Posted on by Matt Thomas

On Nina Van Pallandt: Muse, Witness, Residual Character, and Her Own Woman

Note: Nina Van Pallandt moves through this piece as a kind of drifting hinge figure between art and biography, cinema and scandal, half-real and half-mythologised: from her striking, uncanny presence in Robert Altman’s The Long Goodbye—where she plays the abused, luminous spouse of Roger Wade and becomes, briefly, a kind of muse/anima figure for Philip Marlowe—to her earlier life in the Danish pop duo The Baronets, through her entanglement with Clifford Irving and the great Howard Hughes hoax that later reverberates through Orson Welles’ F for Fake, and onward into the quieter aftermath of fame, reinvention, and partial retreat. The essay follows her not as a stable “character” but as a site where male-authored narratives—Hollywood noir, literary fraud, journalistic myth-making—keep trying (and failing) to fix her meaning, while she keeps slipping free in ways that are at once accidental and oddly deliberate. In the end she becomes something like a case study in cinematic and cultural afterlives: a woman repeatedly written by others, occasionally complicit, sometimes resistant, and finally legible only as a residue of performance, gossip, and unfinished stories that refuse to settle.

I first became aware of Nina Van Pallandt the way most people probably do: not through biography, but through atmosphere—specifically Robert Altman’s The Long Goodbye (1973, The Long Goodbye), a film that feels less like a narrative than a slow collapse of narrative reliability itself. It is a film in which people drift through scenes as if they have forgotten whether they are supposed to be characters or witnesses, and Nina arrives inside it already slightly misfiled, already too composed for the emotional weather she is asked to endure.

She plays Roger Wade’s wife, but “plays” is almost the wrong verb. Altman’s casting logic is not psychological realism in the classical sense; it is something closer to behavioral residue. People are dropped into the frame and asked not to perform identity but to inhabit proximity—to money, to violence, to desire, to failure. Nina’s presence has that peculiar Altman quality: she does not dominate the scene, but she stabilizes it just enough to make everything else look unstable.

Roger Wade (the blocked writer, the alcoholic genius-in-decline) is already collapsing before the plot admits it. Nina is the counterweight that never quite becomes balance. She is care without resolution, intimacy without clarity, the kind of emotional presence that suggests there is a story somewhere but refuses to confirm what it is. And then there is Marlowe, Elliott Gould’s version of Marlowe—half-stoned, half-wandering, permanently a few seconds behind the moral implications of what he is witnessing.

The film keeps staging small ruptures in epistemology. One of the most famous arrives early and feels almost accidental in its perfection: Terry Lennox appearing at 4 AM, asking for a ride to Tijuana. There is a moment—“Tijuana now?”—where Gould’s Marlowe is briefly jolted out of his procedural fog into genuine surprise, as if even he cannot believe how far the plot is willing to drift from explanation. That tonal instability is the world Nina inhabits as well, except she does not get Marlowe’s ironic distance. She gets consequence.

There is a domestic sequence—one of the film’s most disarming—that feels almost out of register with the noir frame: Nina cooking, the soft logic of food and attention, a candlelit dinner shared with Marlowe, where violence and absence are temporarily suspended by something as ordinary as butter and chicken. It is precisely the kind of scene that should resolve emotional ambiguity, but in Altman it does the opposite: it deepens it. Intimacy here is not revelation; it is another form of deferral.

What the film keeps doing, quietly and persistently, is refusing to assign stable moral weight to anyone. Roger Wade is both victim and self-destroyer. Marlowe is both agent and sleepwalker. Nina is both witness and participant, but never allowed the comfort of explanation. Even her suffering—when it arrives—is not narratively sanctified; it is simply another event in a world where events do not accumulate into meaning.

And this is where Nina becomes interesting beyond the film itself. Because she does not resolve into a character arc, she persists as something else: a figure who has been “used” by multiple narrative systems without ever fully belonging to them. In a conventional noir, she would be femme fatale or redemption object or tragic spouse. In Altman, she is none of these cleanly. She is what remains when genre stops enforcing coherence.

What begins to emerge, if one steps back slightly from her, is that she belongs to a broader category of women who are not simply “in” cultural narratives but are written into them by proximity to men who are doing the narrating. The pattern is subtle but persistent: women become legible to the public through the structural gravity of male projects—films, scandals, bands, memoirs—while simultaneously attempting, with varying degrees of success, to assert an interior life that resists that formatting.

It is difficult not to think here of Marianne Faithfull, who occupies a parallel register in the British version of the same phenomenon. Marianne Faithfull is initially rendered publicly intelligible through association—romantic, cultural, chemical—with the Rolling Stones orbit, and specifically through a media ecosystem eager to translate her into a kind of emblem: muse, fallen angel, tragic accessory to male genius. But what is striking about her trajectory is not the initial inscription but the long, stubborn insistence on rewriting it from within.

In both cases—Faithfull and Van Pallandt—the question is not simply “agency” in the abstract liberal sense, but something more structurally constrained: how does a person reassert authorship of self once they have already been written as a function in someone else’s story? Faithfull does this through survival, reinvention, and the eventual authority of her own voice as an artist. Nina does it more quietly, less performatively, by simply not continuing to cooperate with the demand that her life be endlessly narrativized into legible arcs.

And this is where Nina stops being just a cinematic presence and becomes entangled with a second, more volatile narrative system: the world of Clifford Irving and manufactured truth. I remain, in a slightly persistent way, puzzled by Clifford Irving—not in the sense that his actions are obscure, but in the sense that the scale of the gamble still feels oddly disproportionate to the era in which it occurred. Clifford Irving occupies that 1970s threshold where narrative fraud still had room to breathe: before the internet, before instantaneous archival correction, before every claim arrived already cross-checked by a thousand invisible clerks. The rope, in other words, was longer. Not infinitely elastic—but long enough that someone could plausibly believe they might walk it all the way across.

What he did, of course, was fabricate the authorized autobiography of Howard Hughes and briefly convince a publishing system that this fiction was fact. And one cannot quite shake the sense that this sits in a parallel register to Orson Welles’ late-career meditation on forgery and authorship, F for Fake, where the art forger is not simply a criminal but a kind of metaphysical irritant—someone who reveals how fragile the category of “authenticity” already is, even before it is attacked. In Welles’ world, the faker is almost honest about the fact that everyone is faking something. In Irving’s world, the system briefly forgets to notice.

The irony, of course, is that Irving’s fraud depended on a very pre-digital faith in paper trails, intermediaries, and the general slowness of institutional verification. Today it feels almost quaintly physical: forged documents, publishing contracts, phone calls that had to be believed in real time. One can imagine the same scheme now collapsing within hours, not because people are more moral, but because the feedback loops are instantaneous.

And then there is prison. Irving did time—real time, not narrative time—and emerged into a world that had already moved on to other, faster deceptions. Yeah, I mean what did you expect, dude. The arc compresses there in a way that feels almost unsatisfying: scandal, exposure, incarceration, partial reinvention. One wants something more operatic, but what you get is the bureaucratic version of consequence.

The interesting part is not that he was punished, but that for a brief historical window the system was even buildable enough that his plan could function as a kind of temporary reality. That is the shared atmosphere he has with Nina Van Pallandt: not guilt, not innocence, but proximity to narrative systems that were still slow enough to be fooled by their own assumptions.

In later life, Nina becomes harder to place in any of the familiar compartments that earlier decades tried to assign her. The cinematic afterglow fades into cult memory, and the Irving episode recedes into archival texture. What remains is a quietness that feels deliberate rather than accidental—not disappearance, but refusal of continued amplification. She does not convert notoriety into permanent self-mythology in the way later media ecosystems would almost require. Instead, she settles into a lower frequency of visibility: remembered, cited, intermittently revived, but no longer authored by the same pressures that once pulled her forward.

And here the comparison widens again, because what she resembles is not a “sidekick” at all—that word is too structurally comic, too dependent on hierarchy—but something closer to an attendant presence: a figure whose job, in other people’s stories, is to make emotional or moral instability legible without ever fully resolving it.

There is a related category, more neutral and slightly more precise: the faithful interlocutor. Not in the devotional sense, but in the structural one—the person who remains close enough to the main character’s instability to render it speakable, without ever becoming fully absorbed into its explanatory system. Nina performs this function in The Long Goodbyewithout being granted interpretive authority over it.

And there is another: the witness who does not testify cleanly. Not unreliable, but resistant to conversion into stable narrative fact.

We all make mistakes; that much is banal. The more interesting question is what kind of cultural weather those mistakes occur in, and how much agency is genuinely available inside it. Nina Van Pallandt seems, in retrospect, to have lived inside a period when men were still doing a great deal of the writing—of scripts, scandals, explanations—and women were often expected to appear inside those scripts as if they had authored them themselves. Her resistance to that framing is not always loud or declarative. Sometimes it is simply a matter of stepping out of the demand to be continuously interpretable.

And in that sense, what she ultimately carved out is not a grand public myth but something more modest and, arguably, more durable: a minor legacy, lightly held, slightly resistant to over-definition. Not central, not erased, not simplified—just there, in a way that feels unexpectedly intact.

I really like Nina Van Pallandt. In The Long Goodbye, and in the shadow of the Clifford Irving story, it is impossible not to root for her—not because she is resolved, but because she is never fully reducible. She drifts through systems built by men who are busy writing meaning onto the world, and she does not quite consent to being finalized inside any of them. We all make mistakes. She was written into a few. She was also, quietly, a drifter inside Hollywood’s narrative machinery, and what she ultimately leaves behind is a minor but distinct and instinctively cool legacy: not the center of anyone’s story, but one of the few figures who never fully became owned by it.

Posted on by Matt Thomas

On Lou Reed and John Cale’s Album Songs for Drella (aka The Trouble With Classicists)

Note: This post takes up Songs for Drella (1990), Lou Reed and John Cale’s uneasy reunion album/biographical song-cycle about Andy Warhol, moving track by track through Warhol’s trajectory from Pittsburgh outsider to Factory-era icon to post-shooting isolation and mythic afterlife. Along the way it reads the record not just as tribute or elegy, but as a sustained meditation on work, style, and the thin boundary between populist gesture and aesthetic theory—especially in the pointed figure of “classicists” versus Warhol’s downtown anti-orthodoxy. What emerges is less a linear album review than a set of reflections on art, authorship, and cultural literacy, with Warhol as both subject and pretext for thinking about what it means to make anything count as art in the first place.

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In 1990, Lou Reed and John Cale, formerly of the Velvet Underground, latterly famously not getting along, reunited to make Songs for Drella, a tribute/ musical biography of their first patron, Andy Warhol. Drella is a 15 song cycle which takes the listener through Andy’s life and career, from his early days in Pittsburgh, through success in New York, getting shot, latter-day isolation and and loneliness, and ending with an epitaph. The songs fit loosely together in chronological order. Here is the basic scheme: “Smalltown” sees Andy unhappy in Pittsburgh and dreaming of the big city; “Open House” describes the early days of the factory, when all and sundry stopped by and provided Andy with inspiration; “Style it Takes” gives an overview of some of Andy’s famous works and his working method; “Work” explains the considerable work ethic that underlay Warhol’s success; “Trouble with Classicists,” in what is presumably Andy’s voice, provides a series of opinions about “classicists”, “impressionists”, and “personalities”; “Starlight” appears to consider Andy’s flirtation with Hollywood, or Hollywood’s flirtation with him; “Faces and Names” kicks off the second section of the record and finds Andy in despair, something like a midlife crisis; “Images” details Andy’s philosophy of art and hits back at the critics of his method; “Slip Away,” “It Wasn’t Me,” and “I Believe” represent the nadir of the record in which Andy is warned about the people he associates with, confronts a junkie, and is shot by Valerie Solanis; “Nobody But You” sees Andy bereft of companionship hanging out and paying the price of dinner of a nobody; “A Dream” synthesizes all which has come before and puts Andy’s life into fuller perspective; “Forever Changed” sees Andy’s past slipping away; and “Hello It’s Me” represents Reed’s epitaph and apology to Warhol.

Some of the songs are better than others; specifically, I get comparatively little out of “Starlight,” “It Wasn’t Me” and “Forever Changed,” but every song has its place in the story of Warhol’s life and his influence on Reed and Cale, his circle, New York city, and the art world in general. This post will take up the first five songs as a bridge into a wider discussion of the meaning of “classicism” today. There may or may not be a part two to this post.

“Smalltown” is about leaving Pittsburgh, and introduces us to the fact that Andy was gay:

When you’re growing up in a small town
Bad skin, bad eyes – gay and fatty
People look at you funny
When you’re in a small town

New York is more to his liking, and provides a context for his art to flourish:

Where did Picasso come from
There’s no Michelangelo coming from Pittsburgh

I hate being odd in a small town
If they stare let them stare in New York City

The theme of small town boy (girl) made good in the big city is classic and well worn, of course, but Andy thrives in NYC, and soon “The Factory” is open to all comers (“Open House”):

Come over to 81st street I’m in the apartment above the bar
You know you can’t miss it, it’s across from the subway
and the tacky store with the Mylar scarves

Andy wants people around him, and this is one of the major themes of the record; his ability to work is dependent on company and inspiration from associates, peers, and even hangers-on:

It’s a Czechoslovakian custom my mother passed on to me
The way to make friends Andy is invite them up for tea

It’s a Czechoslovakian custom my mother passed on to me
Give people little presents so they remember me

Whereas “Smalltown” is loud and bracing, the music on “Open House” is soft, elegant, gentle even. But even in his halcyon early days in NYC Andy cannot entirely escape the demands of the market or of other people’s ideas of what he should be doing:

I think I got a job today they want me to draw shoes
The ones I drew were old and used
They told me — draw something new
Open house, open house 

You scared yourself with music, I scared myself with paint
I drew five-hundred fifty different shoes today
It almost made me faint
Open house, open house

Andy’s career takes off, and he clearly has something that people want–he has “The Style It Takes.”

You’ve got connections and I’ve got the art
You like attention and I like your looks
and I have the style it takes and you know the people it takes

I’ve got a Brillo box and I say it’s art
It’s the same one you can buy at any supermarket
‘Cause I’ve got the style it takes

Here, Reed and Cale delve into the perennial question of the definition of art–what’s good, what’s bad, and how do we know the difference? The answer which “Style It Takes” seems to offer is: the status of something as “art” is dependent upon someone with “style” telling so. This observation is at once banal (we know art is art because it hangs in a museum and because of the reverent hush of the patrons), and somehow inspiring (a kid from Pittsburgh, “bad skin, bad eyes – gay and fatty,” can take the New York art world by storm simply be possessing some quicksilver attribute called “style,” something so powerful that a simple box of soap pads becomes accepted as art less on its own merit and more on the strength of its association with Warhol, who by 1964 was rapidly ascending to the status of an icon). This song also sees the first appearance on the record of a little group called The Velvet Underground, who Andy “shows movies on.”

“I’ve got a Brillo box and I say it’s art”–is this a populist claim or an elitist one? Is it classical? Certainly not classically classical, but is there not a way in which Warhol’s “pop art”–which is often read as representing the “emptiness” of modern popular culture, is perfectly sincere and actually uninflected with irony? Another major theme of the record is Andy’s work ethic–he was a working artist on whose sweat the whole Factory scene was dependent. Andy’s work ethic, according to Reed and Cale, even had a religious aspect. “Work” starts with Andy in prayer, and despite the neat twist on the phrase “Protestant ethic” here, we are left with the strong feeling that Andy was no self-ironizing dilettante, and that his blue-collar background stuck with him throughout his life:

Andy was a Catholic,
the ethic ran through his bones
He lived alone with his mother,
collecting gossip and toys
Every Sunday when he went to church
He’d kneel in his pew and he’d say,
“It’s work,
all that matters is work.”

He was a lot of things,
what I remember most
He’d say, “I’ve got to bring home the bacon,
someone’s got to bring home the roast.”
He’d get to the factory early
If you asked him he’d told you straight out
It’s work 

In “Work,” Andy stresses quantity over quality; just as he had painted 550 different shoes in “Open House,” here he advises Reed to write like there is no tomorrow:

No matter what I did it never seemed enough
He said I was lazy, I said I was young
He said, “How many songs did you write?”
I’d written zero, I’d lied and said, “Ten.”
“You won’t be young forever
You should have written fifteen”
It’s work

But despite his working artist approach, Andy is not content to merely record the surface of what he sees. Neither, however, is he given to too much soul-searching or self-analysis about why he is who he is, or why he does what he does. “The Trouble with Classicists” is the central song on the record, the song where Reed and Cale get closest to defining Warhol’s attitude toward art. It is also here from which I was moved to take on the issue of classicism in our times:

The trouble with a classicist he looks at a tree
That’s all he sees, he paints a tree
The trouble with a classicist he looks at the sky
He doesn’t ask why, he just paints a sky

The trouble with an impressionist, he looks at a log
He doesn’t know who he is,
standing, staring, at this log {…}
That’s the trouble with impressionists 

If neither classicism nor impressionism, than who or what is Warhol drawn to? The answer is graffiti artists, of all things:

I like the druggy downtown kids who spray paint walls and trains
I like their lack of training, their primitive technique
I think sometimes it hurts you when you stay too long in school
I think sometimes it hurts you when you’re afraid to be called a fool
That’s the trouble with classicists

Let’s dig a little deeper. Cale, who sings “Classicists,” is himself famously a “classically trained” musician, who has drunk heavily of modernism and dissonance without surrendering what I still see as a fundamentally classical musical and aesthetic sensibility. Moreover, writing a song called “The Trouble with Classicists” in this day and age is in itself a classical act. This I think is a key point; whereas once upon a time a Romantic poet could have defined himself or herself in violent opposition to Classicism and made it stick, today, and perhaps even in Warhol’s day, the ability to criticize classicism as a form or style is evidence of a degree of learning and cultural literacy which can only be described as classical, and, yes, a little elitist.

Is this right? It sounds right, at least, and I would add the following: a) the vagueness with which I am approaching the question of a modern definition for classicism in these paragraphs is symptomatic of the generally pitiable state of true learning on that part of what Edward Said calls “the general intellectual”; b) Said’s general intellectual today tends also to be as Dean Williams has said a “profound modernist”–which is a nice way of saying someone who knows, and cares, very little about Western culture’s classical roots, very little about the Bible, very little about the great religion (at least in any fine grained way), probably very little about Shakespeare for that matter; c) today’s general intellectual knows very little about music compared with his 18th or 19th century counterpart. This is a point which Said makes in his chapter on Glenn Gould in On Late Style: “Today’s literary or general intellectual has little practical knowledge of music as an art, has hardly any experience playing an instrument or studying solfege or theory, and except for buying records or collecting a few names like Karajan and Callas, does not as a matter of course have a sustained literacy–whether that concerns being able to relate performance, interpretation, and style to one another, or recognizing the difference between harmonic and rhythmical characteristics in Mozart, Berg, and Messiaen–in the actual practice of music” (115). Any of my general intellectual readership care to take this argument on? If so, please produce 100 words on solfege without reference to Wikipedia before wading in.

My point, which is, I fear, on the verge of getting lost, is less that Warhol or for that matter Reed and Cale are in any specific way “classical,” but that because what Said calls the lack of “sustained literacy” in music on the part of the general intellectual is not confined to music, but extends to art, classical and great literature (how many of us who name drop Aristotle have actually spent any time reading him? how many of us who attempt to evince first-hand knowledge of Marx have actually broached Capital?), and philosophy. That is to say that the general intellectual today is apt not only to be a profound modernist, but also to be a profound generalist, who knows a miniscule amount about a huge number of things, a little bit about a few things, and knows almost nothing is any truly extensive or impressive detail. In this context, not only is “The Trouble with Classicists” deeply classical, not only is Classical Sympathies, by very virtue of its being and intent, classical, but any attempt to engage in a serious way with issues of aesthetic definition marks one out as both a classicist, and at least a minor elitist. Certainly Said, for all his “oppositional” stances and leftist politics, was both–but the question of how leftism and classicism can co-exist is best left for a latter date; it is time to stop work on this post and risk being called a fool.

Posted on by Matt Thomas

On the Film “My Dinner with Andre” Part I: Wally in New York

Note: Opening a multi-part early series from my first blog Classical Sympathies back in 2009, this piece takes up the beginning of Wallace Shawn’s walk through New York en route to his meeting with André Gregory in My Dinner with Andre, using Wally’s voice-over as a lens on artistic precarity, everyday survival, and the comic disproportion between existential weight and mundane errands. The note situates the film’s opening movement as both narrative setup and philosophical framing: a winter city of post offices, xerox shops, and unanswered calls becomes the psychological prelude to a conversation that will later expand into memory, performance, and self-mythology. This installment follows Wally up to his arrival at the restaurant for the pre-dinner drink, where the film’s central encounter is still suspended in anticipation, and meaning is generated less by action than by the act of getting there.

My Dinner with Andre is the famous, or infamous, 1981 film of a dinner conversation between Wallace Shawn, the actor and playwright, and Andre Gregory, the theater director. If I were to make a twofold claim for the film: i) that it is one of the most action packed films ever made, and ii) that it effectively encapsulates the thematics of the entire 20th century, I do not think this would be overstatement. My intent here, however, is not to establish either of these postulates, but rather to simply “blog” the script in the hopes that what needs to be said works its way to the surface. Fair warning: the undertaking will require several posts.

Money crops up on two of the first three pages of the script, and because money, and the lack of it, is a theme that runs beneath the entire script: Andre has money, has the freedom to travel and to spend several years trying to “find himself”; Wally does not. Still, “having money” is, as ever, a relative concept. At the opening of the film, Wally is seen walking through the streets of New York, heading for the restaurant where he is to meet Andre. It appears to be winter, maybe February. In the opening voice-over, Wally ruminates on the life of the artist: The life of a playwright is tough. It’s not easy, as some people seem to think. You work hard writing plays, and nobody puts them on. You take up other lines of work to try to make a living–acting, in my case–and people don’t hire you. So you spend your days crossing the city back and forth doing the errands of your trade. Today wasn’t any easier than any other day. I’d had to be up by ten to make some important phone calls, then I’d gone to the stationary store to buy envelopes, and then to the xerox shop. There were dozens of things to do. By five o’clock I’d finally made it to the post office and mailed off several copies of my plays, meanwhile checking constantly with my answering service to see if my agent had called with any acting work. In the morning, the mailbox had been stuffed with bills. What was I supposed to do? How was I supposed to pay them? After all, I was doing my best (17).

One of the marvelous things about the film is the tongue-in-cheek humor that is rarely, if ever, directly alluded to. A deeply serious film, Andre is also a comedy, a fact which we can recognize because we see that the writers are having fun with the characters who are in turn themselves. That is, Wally and Andre are playing versions of themselves–we assume that most of the experiences that Andre recounts in the film are based on real experiences, and that Wally’s account of his home life is more or less true to life–but exaggerated versions. As Shawn says in the preface to the script, “I knew immediately that {…} I’d have to distort us both slightly–our conflicts would have to become sharpened–we’d have to become–well–characters {…} It would be an enormously elaborate piece of construction” (14). In this initial passage, the humor lies in Wally’s conception of a difficult life: “I’d had to be up by ten to make some important phone calls.”

Wally’s sense of pressure is, from the outset, deliberately out of proportion to the scale of his circumstances. The tone is one of genuine complaint, but the complaint itself is almost comically domestic: the architecture of a “hard day” is built out of errands, envelopes, xerox shops, and an answering service that may or may not contain salvation in the form of an acting job. What Shawn achieves here, and what the film quietly sustains, is a recalibration of seriousness—where existential weight is not attached to grand events but to the texture of administrative survival. Wally’s New York is not a place of romance or revelation, but of circulation: between post office, mailbox, and telephone, as though modern artistic life has been reduced to a loop of deferred contact with recognition.

At the same time, the humor is never fully separable from sincerity. Wally is not merely being mocked; he is also articulating a recognisable condition of artistic precarity, one that the film refuses to glamorize. The genius of the opening monologue lies in this double register: we are invited to laugh at the disproportion between emotional tone and material fact, but we are also made to recognise how easily that disproportion becomes a lived reality. The “dozens of things to do” are not nothing; they are just insufficiently legible as crisis, which is precisely what makes them feel like crisis.

By the time Wally finally moves through the city toward the restaurant, the structure of the film has already been quietly established: this is a world in which meaning is not delivered through events but through the way events are narrated to oneself while walking between obligations. New York, in this sense, is not a backdrop but a medium of self-composition—an environment in which thought is constantly being assembled under mild pressure, as though consciousness itself were an errand.

He checks the time again, as he has been doing throughout the afternoon, and adjusts his route slightly, not out of urgency so much as orientation. The meeting with André already exists in his mind as something slightly unreal, a fixed appointment that has not yet been granted substance by arrival. He crosses another block, passes into the thinning evening light, and begins to approach the restaurant where, for the first time that day, the structure of waiting will shift from solitary to shared.

to be continued…

Posted on by Matt Thomas

On the Song Prince Hal’s Dirge: Confidence, Reformation, and the Politics of Self-Making

Note: This short essay takes Loudon Wainwright III’s song “Prince Hal’s Dirge” as a lens through which to revisit Shakespeare’s Prince Hal in Henry IV, focusing on the idea of self-fashioning across time. It reads Hal’s apparent debauchery and later reform not simply as moral transformation, but as a theory of confidence—either consciously staged, in Shakespeare’s version, or more instinctively internalized in Wainwright’s. Moving between text and song, the piece explores how both versions hinge on the same underlying question: what kind of inner structure allows a self to pass through disorder, delay, and social misreading without collapsing, and to reconstitute itself as effective action when the moment arrives.

Epigraph:

Take me to the ale house
Take me to the whorehouse.
If I vomit, keep me off of my back.

Loudon Wainwright

This piece takes as its source the song “Prince Hal’s Dirge” by Loudon Wainwright III, itself based on Shakespeare’s character Prince Hal from Henry IV. The figure of Hal is one of Shakespeare’s most carefully constructed political selves: a young man who deliberately inhabits disorder in order to make his eventual reformation into kingship appear all the more legitimate, even necessary.

In Henry IV, Hal openly announces this strategy to Falstaff and the other tavern companions:

I know you all, and will awhile uphold
The unyoked humor of your idleness.
Yet herein will I imitate the sun,
Who doth permit the base contagious clouds
To smother up his beauty from the world,
That, when he please again to be himself,
Being wanted, he may be more wondered at
By breaking through the foul and ugly mists
Of vapors that did seem to strangle him.

And again:

So when this loose behavior I throw off
And pay the debt I never promised,
By how much better that my word I am,
By so much shall I falsify men’s hopes;
And, like bright metal on a sullen ground,
My reformation, glitt’ring o’er my fault,
Shall show more goodly and attract more eyes
Than that which hath no foil to set it off.
I’ll so offend to make offense a skill,
Redeeming time when men think least I will.

Hal’s logic is explicit: he will cultivate disorder as a kind of aesthetic and political foil. His apparent immersion in low company is not failure but strategy. Falstaff and the tavern world become, in effect, instruments in the staging of legitimacy.

Paraphrased, Hal is saying: I will live among you for a time, but only in order to abandon you later in a way that maximizes my transformation into kingship. He is a political animal who understands reputation as something staged across time.

Loudon Wainwright III’s “Prince Hal’s Dirge” takes up this same figure, but shifts the emphasis in a revealing way. Wainwright—still best known to many for novelty songs like “Dead Skunk,” though his broader body of work is far more substantial—reimagines Hal less as calculating strategist and more as self-contained performer of confidence within disorder.

The song opens in full immersion in debauchery:

Give me a capon
And some roguish companion,
A wench and a bottle of sack.
Take me to the ale house
Take me to the whorehouse.
If I vomit, keep me off of my back.

Here Hal is not yet strategy, but appetite. The political mask is absent; what remains is the world of consumption, drink, sex, and collapse.

But Wainwright then pivots:

My father, he thinks I’m a good for nothing
that I won’t amount to much.
But he’s not aware of my secret weapon.
I can count on myself in the clutch.

This is the key transformation. Shakespeare’s Hal is self-consciously future-oriented: he plans his reformation as spectacle. Wainwright’s Hal, by contrast, carries an interiorized assurance that he will simply “come through.” The emphasis shifts from calculation to instinctive resilience.

This continues in the song’s martial register:

Show me a breach,
I’ll once more unto it.
I’ll be ready for action any day.
I’ll straighten up, and fly most righteous.
In a fracas, I’ll be right in the fray.
I can drink you under twenty-five tables,
Fight and be a ladies man.
But all this will change,
When I’m good and ready,
To become the king of this land.

The phrase “any day” is doing important work here. It carries the rhetoric of readiness without commitment to timing. It suggests immediacy while quietly deferring it indefinitely. The transformation is always available, never enacted.

What emerges is a different psychological structure from Shakespeare’s original. Shakespeare gives us a political actor who consciously engineers perception over time. Wainwright gives us a man who believes in a durable inner core of competence—someone who can be disordered without being undone.

And yet both versions converge on the same underlying mechanism: confidence as political force. Whether staged (Shakespeare) or internalized (Wainwright), Hal’s power rests on the belief that identity can survive its own contradictions and ultimately reorganize them into legitimacy.

Singing “Prince Hal’s Dirge” before work, I find myself struck less by the irony of Hal’s transformation than by the necessity of something like an unbreakable interior core—something sealed enough to survive fluctuation, failure, and delay, but still flexible enough to return to action when required.

That, ultimately, is what both Shakespeare and Wainwright are circling: not morality, not reform, but the strange political psychology of self-belief under time pressure.

Dedication:

For my father, the biggest Shakespeare lover I know.

Note: If you liked this piece, you may also like the pieces below which also take up various literary works.

On Staying in Business Hotels (Featuring a Little 9-ball)
On Raymond Carver’s “Fires”
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My 20 Favorite Songs of All Time With Commentary

Note: This list speaks for itself, it is simply my 20 favorite songs of all time that include lyrics. For this list I have included extended commentary on each song. When I first published this list it was 110 songs long, and I will publish a full 120 this time in 6 installments. With the first publication, several people let me know that they had discovered new songs from it, and honestly that is the best outcomes I could hope for. This list does not include ambient music or jazz, two genres I also love. This list is a product of nearly 40 years of intensive music listening, so it is, at a minimum, highly curated. Thank you for reading, and may you find a new favorite somewhere on this list.

1. Tulsa Queen — Emmylou Harris.

The greatest song of all time, and it’s not particularly close. I get full body chills and my eyes well up with tears every time I hear it. Emmylou is the greatest vocalist of all time by far, and this song is the clearest possible evidence—not because it’s flashy or showy, but because it is so perfectly, devastatingly controlled. She doesn’t overpower the song; she becomes it. When she starts—“I saw the train/ in the Tulsa night/ calling out my name/ looking for a fight”—it’s just pure magic. The phrasing, the restraint, the sense that the story is already in motion before you’ve even arrived—there is nothing like it. You’re not being introduced to a narrative; you’re being dropped into the middle of one that already feels lived-in, already carries weight.

What makes Tulsa Queen so overwhelming is that it distills everything that makes Emmylou Harris who she is as an artist across her entire career: the fusion of country, folk, and rock sensibilities; the emotional clarity; the ability to inhabit a character without ever losing the self; the sense that every line has been earned. From her earliest work through her later records, she has always been able to locate the emotional center of a song with uncanny precision, but here she doesn’t just locate it—she holds it, perfectly, for the entire duration. It exists in the same emotional universe as something like “Boulder to Birmingham”—another wonderful, better-known masterpiece—but Tulsa Queen goes deeper.

Where “Boulder” is open grief, expansive and communal, Tulsa Queen is interior, private, almost dangerous in how close it lets you get to the narrator’s unrest. It feels less like a performance and more like a confession you were never meant to overhear. There are no words in any language to fully describe the feeling of listening to Tulsa Queen. That’s not hyperbole; it’s recognition. The song operates at a level that bypasses explanation and goes straight to the nervous system. It doesn’t ask to be analyzed—it insists on being felt. The GOAT. Pure legend. Full stop.

2. A Bathtub in the Kitchen — Craig Finn.

My favorite of many possible Finn contenders. Bathtub is about friendship, guilt, redemption, betrayal, and mostly about thankfulness. It’s the greatest song ever written about New York City and also about moving to a big city in general. Finn compresses an entire early chapter of a life into a few lines—the arrival, the uncertainty, the desperation to be claimed by the city, and the friend who makes that possible by opening his door. That friend—Francis—is the emotional center of the song. Twenty years earlier, he’s the one who shows the narrator the ropes, lets him crash on the couch, gives him a foothold when he doesn’t have one. He is, in a very real sense, the reason the narrator makes it at all. And now, in the present of the song, Francis is down and out, struggling, a diminished version of the figure who once seemed stable and generous.

What makes the song hit so hard is the narrator’s response to that reversal. There’s hesitation, even avoidance. He tries, briefly, to pass the responsibility off—to suggest that someone else, someone more put-together, might be in a better position to help. It’s a small moment, almost throwaway, but it reveals everything: the discomfort, the guilt, the instinct to deflect when confronted with a debt that can’t really be repaid. Because that’s the truth the song circles around—some debts can’t be repaid. Not cleanly, not proportionally.

In the end, the narrator does give Francis money—two hundred bucks—but it lands with a kind of quiet insufficiency. It’s something, but it’s not enough, and it never could be. You can’t square that kind of ledger. You can only acknowledge it. And that’s where the thankfulness comes in. Not as a resolution, not as a way of tying things up neatly, but as a recognition that what was given mattered, even if what is returned will always fall short. Finn doesn’t offer redemption in the traditional sense. He offers something more honest: awareness, discomfort, and the attempt—however partial—to do right by someone who once did right by you. It’s a stunning, stunning song and an absolutely worthy number 2.

3,. Faded — Afghan Whigs.

The Afghan Whigs lead singer Greg Dulli does something remarkable here, which is blend swagger, menace, mystery, bravado, and also deep insecurity in one package. Seeing the Whigs play this as the encore at the Paradiso in Amsterdam in 2017 was one of the highlights of my life. It lands as an encore because it has to—it’s the only place a song like this can go. It doesn’t just end a set; it empties it out. Faded closes Black Love, which is not just an album but a fully realized world—cinematic, shadowy, saturated with urban crime, bad decisions, and the kind of late-night moral drift that never quite resolves.

Across the record, songs like Going to Town and Honky’s Ladder are all forward motion and attitude, pure swagger on the surface. But that swagger always feels a little overextended, like it’s covering something fragile underneath. By the time you get to Faded, the cover is gone. What’s been hinted at all along—doubt, damage, a kind of spiritual exhaustion—comes fully into view. There is no mystery as to why this has been the encore for every Whigs show for 30 years.

When Dulli asks to be lifted out of the night, to have someone look down and see the mess he’s in, it doesn’t feel performative. It feels exposed. The bravado is still there, but it’s cracked open, and what comes through is something far more human and far more dangerous. Not only is this the best Afghan Whigs song, Black Love is their best album by a mile. Everything they do well converges there—the mood, the storytelling, the tension between control and collapse—and Faded is the final, perfect release of that tension. He is a genius and the motherfucking man, and Faded is the best of many great Whigs songs. A worthy inclusion at number 3.

4. Every Grain of Sand — Bob Dylan. 

I first heard Every Grain of Sand at 6:30 in the morning on AM radio when Bootleg Series I–III dropped in 1991, and I rushed out to buy the box set—my first ever CD purchase. The song is perfect. It summarizes Dylan’s restless, intense, questioning of his faith and suggests both belief and doubt in a truly majestic way.

To get to a song like this, Dylan had to pass through a dozen different selves. The early pure folk troubadour, the protest voice of a generation, the electric poet of love and surrealism, the mid-period wanderer—all of it accumulates here. By the time he reaches the so-called Christian era, he’s already lived several artistic lives. You can hear the turbulence of that transition in records like Street-Legal, with its overproduction and relative lyrical sprawl, before the much cleaner, more direct Slow Train Coming sharpens the message into something more doctrinal, more certain. And yet Every Grain of Sand doesn’t sound certain at all. That’s what makes it extraordinary.

Even coming out of a period of apparent conversion—shaped, at least in part, by the orbit of his gospel-era collaborators and the intensity of that moment—it refuses to settle into simple testimony. It doesn’t preach. It wavers. It searches. The voice in the song is not anchored; it’s oscillating, moving between conviction and isolation, presence and absence.That tension is everything. Dylan is not resolving faith here—he’s inhabiting it, in all its instability. The sense that there might be something there, and the equally powerful sense that there might not be, coexist without canceling each other out. The song holds both, and in doing so, it becomes larger than any one phase or identity he’s ever occupied. Unbelievable.

The bootleg version—with the faint, accidental intrusion of a barking dog in the background—is far prettier and more soulful than the also great album version. It feels less finished, more human, more exposed—closer to whatever fragile truth the song is reaching toward. It’s 3 on the list, but 1 in my soul.

5. The Traitor — Leonard Cohen.

Cohen’s early career began not as a songwriter but as a poet and novelist—already established in literary circles before he ever stepped into popular music. When he moved into song, it wasn’t a reinvention so much as a translation. Early breakthroughs like Suzanne and later Bird on the Wire introduced a voice that felt unlike anything in contemporary pop: formally literary, emotionally restrained, but spiritually enormous.

Across a career that stretches from that early poetic minimalism to late-period gravity, Cohen repeatedly returned to the same emotional territory in different registers. Seems So Long Ago, Nancy carries quiet tragedy without spectacle. Death of a Ladies’ Man leans into chaos and contradiction. Alexandra Leaving and That Don’t Make It Junk show a late-career clarity—less ornament, more acceptance. And then, right at the end, The Night of Santiago from Thank You for the Dance—completed after his death by his son Adam—feels like a final echo rather than a conclusion, as if the voice is still resolving even after it has stopped.

But it is this passage that sits at the center of everything: “I told my mother, mother I must leave you / preserve my room and do not shed a tear / should rumor of a shabby ending reach you / it was half my fault and half the atmosphere.” Quite possibly the greatest verse ever set to paper.

There is something almost unbearable in its tenderness—the attempt to leave without destroying what you came from, to depart without turning departure into permanent damage. “Preserve my room” is not a realistic request; it is a desire for time to stop, for memory to remain untouched while the self moves forward into uncertainty, drift, and likely failure.

Cohen does something very few writers ever manage: he distributes responsibility without dissolving it. “Half my fault and half the atmosphere” is not an excuse—it is an ethics of existence. The self is accountable, but so is the world that formed it. There is guilt here, but no self-pity. There is clarity, but no absolution. He is naming the condition of being human with a precision that feels almost too large to hold. And what makes the song extraordinary is that it refuses resolution. Cohen never tries to solve the tension he has introduced. Instead, he inhabits it fully.

Across his work—from the early poetic breakthrough to the late songs of acceptance and erosion—he speaks to the quester, the striver, the poet, and the mystic in each of us. Not by offering answers, but by dignifying the act of searching itself. Leaving, longing, failing, seeking—these are not problems to resolve, but conditions to endure with awareness. His voice carries all of it: resignation, yearning, and a kind of quiet, unbreakable grace.

His best by a mile. Simply marvelous.

6. Thrasher — Neil Young.

There are so many great Neil Young songs that could go up here—On the Beach, Roll Another Number for the Road, Albuquerque, Cortez the Killer, Powderfinger. But it’s Thrasher that makes the list. This is a highly allusive, poetic, and suggestive song—TV, the Grand Canyon, diamonds—but it really feels like it’s about the aftermath of the 60s: its disillusionment, its lost promise, the slow realization that whatever was supposed to change didn’t quite change the way anyone thought it would. The idealism curdles, or maybe just hardens. What once felt fluid starts to set.

“They were lost in rock formations / they became park bench formations”—to me, that still reads as a shot across the bow at Crosby, Stills, Nash & Young. Young keeps moving, keeps shedding skins, while the others settle, calcify, become part of the landscape they once tried to reshape. But the line opens up beyond that. “Rock formations” suggests something vast, natural, even awe-inspiring—people absorbed into something larger than themselves. “Park bench formations” is smaller, static, almost resigned—people sitting still, watching instead of acting, becoming fixtures rather than forces. That shift—from movement to stasis, from formation to being formed—feels like the real subject of the song. Not just what happened to CSNY, but what happened to a whole generation that thought it was going to keep moving forever. And then there’s the title.

What the hell is a “Thrasher,” anyway? I mean a thresher is a machine that separates grain from chaff. Something that strips away the unnecessary to get at what’s essential. But a Thrasher? In any case, the song has that quality—it cuts, it reduces, it leaves you with something bare and slightly unsettling. It’s not nostalgic. It’s diagnostic. Young only played it live once, flubbed some lines, and never went back to it. That almost adds to the mystique. It feels like a song that wasn’t meant to be repeated too often, like it captured something too specific, too transitional, to comfortably revisit. The song is delivered in Young’s patented high-pitched voice, with a finely tuned acoustic guitar that gives it a kind of fragile clarity.

It’s a beautiful song and my favorite on a long, long list of great ones.

7. Cape Canaveral — Conor Oberst.

The most beautiful and striking song from Conor, who also wrote my number 13 favorite, Easy/Lucky/Free. The song uses the space program—those televised launches, the spectacle of rockets lifting off into the unknown—as a proxy for growing up in America in the latter part of the 20th century. It’s about distance, aspiration, and the strange way memory reshapes people and moments over time.

It is one of the most gorgeous American songs ever written. “I watched your face age backwards / changing shape in my memory / you told me victory’s sweet / even deep in the cheap seats.” That might be one of the prettiest passages ever set to music. Oberst is doing something subtle and devastating here—he’s taking the language of triumph and reframing it from the margins. Victory’s sweet even deep in the cheap seats is not a grand statement; it’s a salvaged one. It’s about making meaning from distance, from partial access, from watching instead of participating.

That’s what the whole song feels like: an attempt to construct something lasting out of fragments—TV images, half-remembered conversations, the emotional residue of growing up. The rockets go up, but the song stays grounded in what it felt like to watch them, to want something more without knowing exactly what that “more” was. Full body chills every time. Conor is my number 5 artist of all time, and this song is exactly why.

8. It’s Never Been a Fair Fight — Craig Finn.

I have written at great length about Fair Fight elsewhere, and this is the song that I have the most to say about. Mostly, this is because it is one of Finn’s, and music’s, most intellectual song and it takes up the somewhat unlikely theme of the rules and strictures of musical subcultures.

Craig Finn himself has commented on this song and says that “It’s Never Been A Fair Fight”: “Is about the extreme difficulty of staying true to the rigid rules of a subculture as you get older. The character in the song revisits an old peer and finds struggle and disappointment in the place he left behind.” The song sees the narrator describing his old stomping grounds with his ex-lover Vanessa, the purist who is the keeper of the rules of the subculture of hardcore, underground music scene, as well as Angelo and Ivan, fellow scenesters.

The song sees the narrator leaving the culture because he heard a song that he liked on the radio. Pop lusic is verboten in Vanessa’s world, but not in that of the narrator or Finn. Too many goddamn rules. The song closes with a. funeral and what sounds likea suicide, maybe Angelo, and Finn closes the song thusly: Yeah, I knew he was hurting I was not exactly walking in bright lights Yeah, I knew it could happen It’s never been a fair fight.” Life, for many of us, can feel like it’s not a fair fight. Making it in music, or in New York, probably doesn’t feel like a fair fight.

A lot of fights are not fair. Finn is a magician and this is one of his greatest magic tricks. 

9. Never Aim to Please — Tommy Stinson.

Tommy Stinson, the bassist from The Replacements—went on to have, in my opinion, an even better solo career than the band’s lead singer Paul Westerberg. And considering that Westerberg is a genius and an absolute legend, this is saying something.

Stinson was barely out of childhood when the Replacements were at their peak—a teenager holding down the low end in one of the most chaotic, brilliant bands of their era. That early immersion shows up everywhere in his later work: the instinct for melody, the looseness, the sense that a song should feel lived-in rather than perfected. But what’s striking about his post-Replacements career—through Bash & Pop and his solo records—is how much he refines that instinct. The pure thrash and glorious sloppiness of early Replacements material gives way to something sweeter, more polished, but never sanitized. The edges are still there; they’re just better framed.

Never Aim to Please comes from Bash & Pop’s first record, Friday Night Is Killing Me, and Stinson has alternated between Bash & Pop releases and solo records over the 35 years since the Replacements broke up. In the first verse, Stinson sings about the absence of a point of view, and that marvelous line always reminds me of Westerberg’s writing on “Someone Take the Wheel”—that same sense of dislocation, of trying to find footing in a world that keeps shifting under you. There’s a great anecdote from Westerberg that early on, the Replacements pretended to hate The Rolling Stones—it was part of the pose, the punk posture. But it was just that: a pose. They actually loved the Stones.

And you can hear that lineage clearly in Stinson’s work. For all of his originality, he’s very much working in that classic rock tradition—songcraft, groove, emotional directness—but he does it in the best possible way, without nostalgia or mimicry. It feels inherited, not borrowed. Stinson may not claim to have a point of view in this song, but he’s been a remarkable curator and keeper of the Replacements’ legacy, especially as Westerberg has retreated from the music scene over the last decade. There’s a quiet authority in that, a sense of continuity that runs through his work. And the song itself? It just fucking kicks. It hits me in all the feels every time, and it is a worthy number 9.

10. My Life Is Sweet — Simon Joyner.

“Met the drinker for a drink/ back when I was drinking everything but the kitchen sink”—and sure enough this song is about drinking, and drunks. Joyner’s friend is an alcoholic, and at the time of writing so is Joyner. They go to a bar and sit together, talking a little, mostly not, letting the night pass in that particular way that only two people who know each other well can manage.

Ultimately, this song is about male companionship, and how a quiet drink with a quiet friend can be life-saving when you really need it. Joyner takes a taxi home—drunk, or hungover, or somewhere in between—and collapses on the floor. And then the song ends with that extraordinary sequence where the city drops away, becomes something almost beautiful from a distance, and he arrives at that fragile, hard-won conclusion: my life is sweet. Anyone who is, or has been, a drinker will immediately recognize what Joyner is doing here—he is rationalizing the unrationalizable, but at the same time he’s not lying about it.

Is drinking so, so sweet? Yes and no, of course—and that tension is the point of this truly magnificent song. Part of what makes Joyner so compelling is how deeply rooted he is in the Omaha scene that would later produce Conor Oberst. Joyner is the elder figure there—born in 1971, a few years ahead of Oberst, who came up in the early ’80s generation—and his influence on Conor is both documented and unmistakable. Oberst has cited Joyner as a major influence, and you can hear it: the diaristic honesty, the willingness to let a song feel unfinished, the comfort with contradiction.

Joyner was mapping that terrain before it had a name, and before it had an audience beyond the local. He’s also massively underrated. He has other great songs—Fearful Man, One for the Catholic Girls—but My Life Is Sweet feels like the purest distillation of what he does best. There’s no artifice, no attempt to resolve the contradictions he’s living inside. Just a voice, a night, a friend, and the uneasy grace of getting through it. Anyone who’s been there knows: that’s more than enough.

11. Red River Shore — Bob Dylan.

I first heard Red River Shore the same way I heard a lot of Dylan that mattered to me—by accident, or what felt like accident at the time, buried in the sprawl of one of his Bootleg records. It didn’t announce itself. It just was, sitting there, waiting, and then suddenly it wasn’t just another outtake—it was the thing I couldn’t shake.

This is Dylan at his most haunted and most restrained. No overproduction, no grand gestures, no myth-making machinery humming in the background. Just a voice, a melody, and a memory that refuses to settle. If something like Street-Legal feels overstuffed and restless, and even the later Time Out of Mind leans into atmosphere as a kind of emotional amplifier, Red River Shore strips all of that away. It’s clean, but not simple. Bare, but not empty. The song circles around a figure—maybe a woman, maybe an idea, maybe a version of the self that no longer exists—and it never quite resolves what that figure is. That ambiguity is the whole point. Dylan doesn’t give you a stable object to hold onto; he gives you the feeling of reaching for something that keeps receding.

The “shore” itself feels less like a place and more like a threshold, somewhere between memory and myth, where the past is always just out of reach but never fully gone. And then there’s that extraordinary turn in the middle of the song, where he brings in the story of a man from long ago who could raise the dead—a clear echo of Jesus, or at least of the idea of miraculous restoration. Dylan had already passed through his overtly Christian phase by the time this surfaced, but what’s striking is how the language of that period never really leaves him. It just changes form. Here, it’s not testimony. It’s question. If that kind of power once existed—if something lost could be brought back—what does it mean that it doesn’t seem to happen anymore? That question lands hardest when he turns back inward, toward his own invisibility. There’s a line of thought that runs through the song: maybe nobody ever saw him at all, except for that one figure from the shore.

It’s devastating in its quietness. Not anger, not even sorrow exactly—just the possibility that a life can pass largely unrecognized, that meaning can hinge on a single encounter that may or may not have been real in the first place. What’s remarkable is how controlled the longing is. Dylan has written plenty of songs that ache, that burn, that lash out, but this one doesn’t do any of that. It waits. It moves at the pace of recollection, not desire. There’s a sense that whatever happened on that shore is no longer accessible in any direct way, and yet it exerts a gravitational pull on everything that comes after. The narrator isn’t trying to get back there—he knows he can’t. He’s trying to understand why it still matters.

And like the best Dylan songs, it resists interpretation even as it invites it. Is this about a lost love? A spiritual dislocation? A life not lived? Yes, and no. It holds all of those possibilities without collapsing into any one of them. It’s a song about memory as an unstable medium—how it distorts, preserves, elevates, and traps all at once. There’s a quietness to the performance that makes it feel almost private, like something not meant for a wide audience. That’s part of why it lands so hard. It doesn’t feel like a statement; it feels like a confession overheard, or maybe even a thought that slipped out before it could be edited.

Dylan has written hundreds of great songs across more phases than most artists could survive, but Red River Shore sits in a category of its own. It doesn’t rely on his persona, his legend, or even his voice at its most forceful. It relies on something deeper: his ability to inhabit uncertainty without trying to resolve it. That’s why it stays with you. Not because it explains anything, but because it refuses to.

12. April the 14th Part II— Gillian Welch.

I first heard April the 14th, Part II the way a lot of the best music enters your life—over the radio, half by accident, but not really. Conor Oberst had cited it as one of his favorites, and that was enough to lean in, but the song itself did the rest. It didn’t ask for attention; it quietly demanded it. Welch’s partnership with David Rawlings is one of the great creative pairings in American music—two artists so attuned to each other that the line between writer and interpreter almost disappears. Across an extraordinary catalog, they’ve built a sound that feels both ancient and immediate, rooted in tradition but never derivative. April the 14th, Part II sits right at the center of that achievement.

The song takes its title—and its loose conceptual grounding—from the date of Abraham Lincoln’s assassination, but it doesn’t approach history in a straightforward way. Instead, it fractures it, reframes it, turns it into something lived-in and contemporary. The past isn’t something to be preserved behind glass; it’s something that leaks into the present, reshaping it in ways that aren’t always obvious. Lincoln is there, but so are highways, bars, long drives, and the peculiar loneliness of being in motion for too long. That’s where Welch’s genius shows most clearly. She understands the continuity between those worlds—the mythic American past and the far less romantic present of touring musicians, late nights, and empty miles. When she drops a line about a girl passed out in the backseat, it doesn’t feel like an aside. It feels like evidence. She knows the road—not the idea of it, not the mythology, but the actual, grinding, disorienting reality of it. The song carries that knowledge without ever turning didactic.

There’s also something deeply American in how she holds all of this together. Not patriotic, not sentimental, but recognizably American in its contradictions—history and amnesia, ambition and exhaustion, beauty and wreckage. In that sense, she stands in a clear lineage with artists like Townes Van Zandt and Emmylou Harris, inheriting their sense of narrative, their attention to emotional truth, and their ability to let a song breathe without forcing it toward resolution. And yet she never feels like an imitator. The voice, the phrasing, the perspective—it’s all distinctly her own. A true American original. April the 14th, Part II doesn’t resolve its tensions. It lets them sit. History and the present, myth and reality, movement and stasis—they all coexist without collapsing into something neat. That’s what gives the song its weight. It’s not trying to tell you what America is. It’s showing you what it feels like to live inside it. And once you hear it, you don’t forget it

13. Easy / Lucky / Free — Bright Eyes.

I love Bright Eyes, but I love Conor Oberst solo even more—Cape Canaveral sits higher for me—but Easy / Lucky / Freeis a killer. It’s one of those songs that feels light on the surface—almost buoyant—but carries a depth that sneaks up on you. That’s a rare trick, and Oberst pulls it off without seeming to try. The song moves with an ease that belies how much is actually going on underneath. There’s reflection, acceptance, a kind of cautious optimism that never tips into naïveté. It feels like someone taking stock of a life that’s been messy, uncertain, sometimes self-destructive, and deciding—quietly—that it’s still worth something. Not in a grand, declarative way, but in a lived-in, almost offhand recognition.

Part of what makes the song endure is how open it is. It doesn’t force a meaning; it leaves space for you to step into it. That’s something Oberst has gotten better and better at over time. The earlier Bright Eyes records—I’m Wide Awake, It’s Morning, for instance—are incredible, but they’re more immediate, more raw in their expression. By the time you get to Digital Ash in a Digital Urn, which I think is the best Bright Eyes record, the songwriting has deepened. There’s more control, more subtlety, more willingness to let a song breathe. Easy / Lucky / Free sits right in that evolution. It’s not trying to overwhelm you; it’s trying to stay with you. And it does There’s also a great conversation around the song in its afterlife.

The Dawes cover is marvelous—faithful but expanded, bringing a different kind of warmth and clarity to it. And then there’s the reciprocal moment: Oberst covering Million Dollar Bill, Dawes’ best song, on their collaboration. It’s a perfect exchange—two artists who clearly hear each other, trading songs and making them their own. Oberst is my number five artist of all time, and it’s songs like this that make that ranking feel inevitable. The songwriting has only gotten deeper with time, more assured without losing that early vulnerability. And even though Cape might sit higher, Easy / Lucky / Free is right there, doing something just as difficult in a completely different register. So, so good.

14. Double — Michael Knott.

This song sits as part of a remarkable one-two punch in Knott’s catalog—Double at 14 and Rocket at 15. Rocket is the better-known, more frequently covered song, the one that tends to travel. But Double might actually be the deeper cut, the one that does more with less and lingers longer once it’s over. On its face, the song is almost disarmingly simple: a guy at a bar knocks over another guy’s drink at the pool table, offers to replace it, and the other guy asks for a double instead. The narrator digs out four bucks—his last—and buys it.

That’s the whole setup. It’s small, almost nothing. A minor act of compensation in a place where those transactions happen all the time. But Knott is never just writing the surface story. What unfolds underneath is something much heavier, something that shifts the song from anecdote to diagnosis. The bar becomes a threshold space—where the choices you make, even small ones, echo into the life waiting for you at home. The song moves forward and suddenly you’re not at the pool table anymore; you’re waking up in a house with responsibilities you can barely face. A child needs you. Your partner is trying to hold things together. There’s church, obligation, the faint outline of a life that’s supposed to be stable and meaningful, and the overwhelming sense that you are not meeting it.

And then Knott does something devastating: he reframes the entire situation through another failing marriage—the preacher, the supposed moral center, the guiding light for years, whose own life is unraveling. The implication lands hard and quietly: if even that doesn’t hold, what chance does anything else have? The song becomes about marriage—not in the sentimental or idealized sense, but in the lived reality of it. Fatigue, compromise, small resentments, moments of grace that don’t quite offset the weight of everything else. The double at the bar starts to feel like more than a drink—it’s a decision, a coping mechanism, a tiny tilt in a direction that’s already dangerous.

Knott’s work has always carried that edge of autobiography, that sense that he’s not writing about struggle so much as from within it. His battles with alcohol were real, long-standing, and central to both his life and his art—something he never fully resolved, only wrestled with in public through his songs. But while that struggle shaped him, it is not officially cited as the cause of his death, which remains undisclosed.  What makes Double so powerful is how much it trusts the listener. It doesn’t explain itself. It doesn’t moralize. It presents a series of moments—bar, home, church—and lets you connect them, lets you feel the throughline without being told what it is. And once you see it, you can’t unsee it. That’s why it might be Knott’s best song, even if Rocket gets the attention. Double doesn’t announce itself. It just sits there, quietly devastating, doing its work long after the song is over.

15. Rocket and a Bomb — Michael Knott.

This is Knott’s best-known—and, for many people, only known—song. It’s the one that traveled beyond the small, fractured world he spent his career navigating, the one that people who don’t know the rest of his catalog can still recognize. And that’s fitting, because it captures almost everything that made him singular. Knott never fit comfortably inside the Christian rock community that was supposed to be his home. He clashed with labels, bounced from one situation to another, tried repeatedly to start his own imprints just to maintain control of his work, and spent much of his career existing in the margins of an already marginal scene. There were too many expectations, too many rules about what a “Christian artist” was supposed to sound like, what he was supposed to say, how cleanly he was supposed to resolve things. Knott refused all of it.

You can hear the lineage—artists like Larry Norman laid some of the groundwork—but Knott is no inheritor in the traditional sense. He’s a total original. Where Norman and others often leaned toward proclamation, Knott leaned into contradiction, mess, unresolved tension. He wasn’t interested in presenting faith as an answer; he was interested in showing what it felt like to live inside it when the answers didn’t come.

His career reflects that restlessness. From the early chaos of Popsicle and Popsavers, through the darker, more aggressive phases of L.S. Underground and LSU, into his solo work and projects like Aunt Betty’s, Knott kept shifting forms, refusing to settle into anything that could be easily categorized. The sound changed, the bands changed, the labels changed—but the core impulse didn’t: tell the truth as he experienced it, even if it didn’t line up with what anyone wanted to hear. Rocket and a Bomb distills all of that into something deceptively simple. There’s humor in it, almost absurdity—“Mr. God, is there a Ms. God? Can she help me find a job?”—but it lands because it’s so nakedly real. This is a man of Christ who is also a man of the world, standing in the gap between those identities, not reconciling them but living them both at once. He’s not asking for salvation in the abstract; he’s asking for something immediate, practical, human. He just needs a goddam job.

That tension runs through everything he ever said and did. His line—“I know Christ. It doesn’t make me good; it doesn’t make me bad; it doesn’t make me anything. It just means I know Christ.”—might be the clearest articulation of his entire ethos. Faith is not a moral upgrade, not a solution, not a transformation you can point to and quantify. It’s a relationship, and relationships are messy. So what is a rocket and a bomb? They’re things most people don’t get to touch. Power, transcendence, impact—forces that exist beyond the everyday. The narrator wants a job, something stable, something achievable. But he also wants more. He wants access to something larger, something explosive, something that breaks the limits of an ordinary life. Knott lived that contradiction. He lived fast, pushed hard, refused to smooth out the edges that made him difficult to categorize or contain. He burned through systems that couldn’t hold him, left behind a body of work that feels both deeply personal and strangely universal. He had to.

16. There Must Be More Than Blood — Car Seat Headrest.

This is a tricky one, because it forces us to deal with a shift—not just in a song, but in an artist. My thesis is that this is Will Toledo going into a kind of relative hiding, and the song reads like a document of that transition in real time. His early work—from Beach Life-in-Death through Nervous Young Man to Sleeping with Strangers—was as direct, as exposed, as heart-on-the-sleeve as anything in the last decade of rock music. He wasn’t just confessional; he was incapable of not being confessional. He was the heart on his sleeve songwriter of his generation. You didn’t have to work to understand him—you just had to be willing to feel what he was feeling.

And then you put that next to someone like John Darnielle—super prolific, deeply lofi in his early approach, but always a little more mediated, a little more constructed. Darnielle throws his material against the wall and lets it accumulate into narrative. Toledo, at his best, just bleeds. So when Making a Door Less Open arrives, even the title signals a shift. Something is closing. Something is being sealed off. The masks—first the normal face coverings, then the Trait mask, then the gas mask—aren’t just stagecraft. They’re statements. The question isn’t “what is he hiding?” but “why does he suddenly feel the need to hide at all?” There Must Be More Than Blood sits right in the middle of that tension. You get these images of dislocation—of a life that used to feel rooted and now doesn’t. The delta, the shoreline, the houses stripped away—it doesn’t read like a literal disaster so much as an internal one. The sense of ground disappearing. Of structures—family, identity, whatever “home” used to mean—losing their coherence. He talks about wasting time, but you know that’s not true. He’s one of the most prolific songwriters around. What he’s really describing is a shift in how that time feels from the inside.

And then there’s the second movement—the red-eye flight, the self-recognition that barely qualifies as recognition at all. He sees himself, but only as an outline, a set of lines without substance. That’s the real break from the early work. The old Toledo was hyper-present, almost overwhelmingly so. This Toledo is thinning out, becoming harder even for himself to locate. So what do you do when you can’t see yourself clearly anymore? You disappear further. You become, in a sense, the Invisible Man. That’s what the masks start to feel like—not affectation, but adaptation. A way of dealing with a self that no longer feels stable enough to present directly. And if you follow that thread forward, you get to The Scholars—The Scholars—his most recent record. It’s even more oblique than Door. There are great songs there—Stay With Me (I Don’t Want to Be Alone), Equals—but they’re harder to parse, less immediately accessible. The emotional core is still there, but it’s buried deeper, refracted through more layers.

Part of that may simply be life catching up with him. Toledo dealt with serious health issues in the lead-up to that record—long COVID, histamine intolerance—and the process became more collaborative, less singularly driven. That alone changes the texture of the work. The lone voice becomes one voice among several. The signal diffuses.So There Must Be More Than Blood starts to feel like a hinge point. The moment where the old mode—pure exposure, pure immediacy—begins to give way to something more guarded, more fragmented, more difficult to access. But the core hasn’t disappeared. It’s just harder to reach. And that’s why the song matters. It captures an artist in the act of losing something essential—or at least transforming it into something less direct, less available, maybe even less comforting. Will Toledo is a mysterious guy. Deep, fragile, a little haunted, clearly carrying more than he lets on. He’s dealt with some tough stuff, and you can feel it in the way the work shifts over time. And for anyone still saying “rock is dead”—they can fuck off. There is still The Hold Steady and Car Seat Headrest making records that matter, records that wrestle with something real. You just have to be willing to meet them where they are now, not where they used to be.

17. Oh My Sweet Carolina — Ryan Adams.

One of the most beautiful and sad songs in modern American songwriting. The record Heartbreaker—Adams’ solo debut after his run fronting Whiskeytown—remains his peak for many listeners. It’s also the album where everything still feels unforced: the writing, the pacing, the emotional exposure. Later records like Gold brought wider recognition, and something like Chris gets close in flashes, but Heartbreaker has a coherence of mood that he never quite replicated.

What defines Oh My Sweet Carolina is its dual perspective. On the surface, it’s a travel song—young man on the road, drifting through cities like Cleveland, accumulating damage, spending energy and money with a kind of reckless momentum that feels both chosen and inevitable. But underneath that motion is something much older: a pull backward, toward origin, toward a place that isn’t just geographic but emotional. North Carolina isn’t just home—it’s coherence.

The Cleveland passages (So I went on to Cleveland and I ended up insane/ I bought a borrowed suit and learned to dance/ And I was spending money like the way it likes to rain/ Man, I ended up with pockets full of cane) carry that classic Ryan Adams contradiction: charm and collapse in the same breath. The narrator moves through instability with the confidence of someone still convinced that motion equals meaning, even as that belief is starting to fail him. It’s the sound of someone learning, mid-stream, that movement alone doesn’t resolve anything. And then the emotional center of the song reveals itself: (Oh mw sweet Carolina/ what compels me to go/ oh, my sweet disposition/ may you one day carry me home), the longing not just to return, but to be returned in one piece. Not improved, not transformed—just intact.

This is where the collaboration with Emmylou Harris matters. Her voice doesn’t decorate the song; it stabilizes it. It sounds like witness. Adams has written other songs that brush this same emotional territory—English Girls Approximately, Oh My God, Whatever, Etc., Still a Cage, Birmingham—but none of them quite hold the same balance of youth and exhaustion, romance and reckoning. Oh My Sweet Carolina feels like a hinge between those states: a young man already speaking like he understands what the older version of himself will miss. It’s a debut record moment that feels strangely final. A song about going forward that only makes sense when you understand what it costs to leave things behind. A truly majestic entry—and a worthy entry here at 17.

18. Killer Parties — The Hold Steady.

Everything else is commentary. The band isn’t just a band; Finn isn’t just a frontman. The Hold Steady is a community, a lineage, a shared memory palace built out of long nights, near-misses, inside jokes, loud guitars, and people who actually want to be there. We are the Hold Steady. And Craig baby you are goddamn right, I am the Hold Steady. The Hold Steady is my favorite rock band of all time. I could make the case for a few others—The Velvet Underground, Grateful Dead, The Replacements, Car Seat Headrest—but for my money The Hold Steady most cleanly expresses what rock music is for. Not just sound, not just attitude, but shared experience turned into narrative.

Coming out of Lifter Puller, Finn was already writing in tight, clipped internal rhymes, dense alliteration, and nocturnal fragmentation. But with The Hold Steady the perspective opens up. The chaos is still there, but it’s filtered through memory and reflection. The language becomes more legible without losing its edge. Killer Parties, from the 2003 debut Almost Killed Me, is told from the perspective of someone older, someone who has already lived through the hardcore-to-indie-to-rave-up continuum and come out the other side. He’s been through Minneapolis basements, New York nights, Ybor City mythologies—the so-called party capital of America—and what remains is not nostalgia exactly, but accounting.

What did it cost, and what did it mean? It pairs naturally with Most People Are DJs (“I was a Twin City trash bin / I’d jam it all into my system”) and Soft in the Center (“And I’m just trying to tell the truth, kid / I’m just trying to tell the truth / You can’t get every girl / You get the ones you love the best”). Across these songs, Finn is already moving toward the older register he occupies now: less urgency, more reckoning. Like Faded in the Afghan Whigs canon, Killer Parties has remained a live staple—an encore song, a release valve, a communal shoutback. And its central refrain is exactly what it says it is: killer parties almost killed me.

No metaphor is needed beyond that. Finn has been there and done that. He has lived it, absorbed it, and returned from it with something closer to clarity than regret. And even in this early form, you can already hear the direction of travel: toward the reflective, grounded, older voice that defines him now. A truly great song—and a blueprint for what comes after the chaos stops being infinite.

19. Rock n Roll Singer— Mark Kozelek (AC/DC Cover).

The original Rock ’n’ Roll Singer is by AC/DC—a raw, early cut from T.N.T. (1975). It’s already got the skeleton of something great: the ambition, the defiance, the simple declaration of identity. But it’s also messy in that early AC/DC way—loose production, Bon Scott’s sardonic asides cutting across the sincerity, a kind of pub-rock sarcasm that slightly diffuses the emotional core instead of locking it in.

Kozelek hears it differently. And more importantly, he means it differently. Across multiple incarnations—solo, Red House Painters, and Sun Kil Moon—he’s returned to this song like it’s a personal doctrine. It’s not a cover so much as a repeated self-interrogation. The acoustic version strips everything down to confession; the Sun Kil Moon electric version adds weight and repetition; but it’s the live performance at The Chapel in San Francisco (Aug 19, 2017, on YouTube) that feels definitive. Electric guitar, but unpolished. Less mannered than the studio SKM version. More immediate. More exposed. And Kozelek just inhabits it.

The lyric isn’t complicated: working-class childhood, parental expectation, school, rebellion, long hair, refusal to conform. It’s the classic origin myth of rock music itself. But in Kozelek’s hands it becomes something more existential. Not just “I want to be a rock singer,” but this is the only coherent identity available to me that feels real. That chorus—repeated, rising, almost mantra-like—isn’t just aspiration. It’s fixation. He pushes it harder each time, voice tightening, almost ecstatic. There’s a strange joy in it, but also something like compulsion. This is not a person imagining a career. This is a person locking onto a destiny.

And then the darker undercurrent: the devil-in-the-blood logic of ambition. The sense that the desire itself has a cost baked into it. Kozelek doesn’t play that as metaphorical flourish; he plays it as recognition. If you want this badly enough, you don’t just chase it—you surrender something to it. That’s why it works as his thesis statement. Because Kozelek’s entire career is that tension stretched over decades. Early Red House Painters records gave him Have You Forgotten and Cruiser—songs of melodic melancholy and emotional clarity. Then the Sun Kil Moon era brings the breakthrough again with Benji (2014), an album that suddenly re-centers him in the conversation. “Ben’s My Friend” in particular catches that strange inversion of time and status—his connection to Ben Gibbard now reframed through shifting fame and distance, with that brutal line about the thin line between backstage access and feeling like an impostor in your own life.

From there, things expand—and fragment. The later Sun Kil Moon output becomes looser, more digressive: breakfast details, cats, long spoken passages, emotional drift that sometimes feels like composition and sometimes feels like overflow. The public persona starts to wobble. He writes songs like War on Drugs Can Suck My Cock after disputes over live volume at festivals. A collaboration with Jesuturns into extended monologue rather than song structure. He comments on audience demographics, once saying he used to play for “cute chicks” and now plays for “guys in tennis shoes.”

The self-mythology becomes unstable—at times self aggrandizing, at times self-undercutting, often both in the same breath. Then there are the controversies, the accusations that circulate without ever fully resolving into clean narrative closure. Combined with the relentless release schedule—multiple records a year, nearly impossible to track in full—it creates a figure who is always present and slightly out of phase with how he is being received. And yet. And yet he still lands inside my personal canon. Because at his core, Kozelek keeps returning to that original statement: I wanted to be a rock ’n’ roll singer, and I became one. Everything else—digression, controversy, excess, fatigue—is built on top of that irreducible core.

My great friend Ian (who thinks I’m nuts for still following him, despite also loving Red House Painters) isn’t alone in that reaction. Kozelek divides listeners precisely because he refuses to stabilize into a single, manageable artistic identity. But for me Singer remains clean. Not in execution, but in intent. A mantra. A declaration. A life chosen and lived, even when it gets strange. And that’s why it sits so high for me: not because it’s simple, but because it’s absolute.

20. Malibu Love Nest — Luna.

The simplest song in the top 20 and also the silkiest. First things first: Sean Eden, Luna’s long-time guitarist, is an absolute genius. His playing sits in that rare tier—alongside people like Mick Taylor or Mark Knopfler—where the instrument stops sounding like accompaniment and starts sounding like commentary. He doesn’t decorate the song; he inhabits it.

And by all accounts, he had to work for that role. In Dean Wareham’s memoir Black Postcards, there’s that wonderfully deadpan passage about Bryce reorganizing Sean’s process:
“Sean is a brilliant guitarist… but he is one of these people who equates the music-making process with a great deal of pain.”

That line captures something essential about Luna: the tension between ease and effort. The music feels effortless, but it absolutely isn’t. Once Eden joins the band, everything lifts. Luna becomes something more refined, more cinematic, more self-aware without losing its cool distance. Malibu Love Nest—from Rendezvous, which for my money is their best record (though Penthouse is right there)—is the clearest expression of that shift. It’s also my favorite Luna song by a distance, ahead of Chinatown, Tiger Lily, and Slash Your Tires.


On the surface, it’s almost disarmingly simple. Romantic imagery, luxury signifiers, travel, repetition of place-name refrain. A kind of dream-pop postcard written in real time. But Wareham is doing something subtler: he’s writing the fantasy while simultaneously showing you its constructedness.
The lyric moves through diamonds, bathrooms, planes, buses, trains, Italian magazines, streets, beaches—all the surfaces of a life that looks expensive and weightless from the outside. But the repetition of writing a name in all these places gives it away. This isn’t possession. It’s inscription. It’s someone trying to leave evidence inside a world that may not actually be theirs.

And that’s where Britta Phillips comes in—not just as bassist, but as tonal shift. Her presence gives the song its low-end pulse, that understated, sultry movement that turns the whole thing from detached dream into something bodily. Luna stops being just a guitar band and becomes something more fluid, more intimate, more ambiguous.

There’s also that Black Postcards anecdote about Wareham in therapy after his divorce, where he’s asked whether he’d prefer $200 or $150 per session and immediately says $150. It’s funny, but also perfectly revealing: the instinct toward practicality inside a life that otherwise drifts toward aesthetic distance. That’s Luna in miniature—romance always checked by cost, beauty always adjacent to accounting.

And then the final shift: “You will call me Robespierre…” Suddenly the dream cracks open into history, revolution, collapse, irony. The romantic fantasy is no longer just private—it’s unstable, politicized, slightly unmoored. The air changes.

That’s what makes Malibu Love Nest work. It’s not just a soft-focus love song or a beachside reverie. It’s a controlled drift between aspiration and awareness—between the life being imagined and the life quietly acknowledging it might never quite arrive. Silk on the surface. Restlessness underneath. A perfect Luna move.

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On Subcultures and Scenes in Craig Finn’s “It’s Never Been a Fair Fight”

New Note: It has been a little while since I last posted this piece, and I’m glad to bring it back into view. It remains my very favorite essay on the Kyoto Kibbitzer, and has continued to circulate far beyond what I ever expected, with many hundreds of reads over time. In an entirely unscientific but pleasingly persistent corner of the internet, it still seems to rank #2 in search results for the term “Katie Park Bad Moves,” just behind Wikipedia, which is pretty cool. I have no idea what to make of that, but I’m not complaining.

The piece itself—on Craig Finn’s “It’s Never Been a Fair Fight”—has always felt to me like one of the most complete things I’ve written about music, scenes, and subcultures, and I’m grateful for the continued readership and responses it has received. Reposting here in full for anyone who missed it the first time around, or wants to revisit it.

Original Note: This piece is about an absolutely amazing song by Craig Finn called “It’s Never Been a Fair Fight” released in 2020 on All These Perfect Crosses from Partisan Records. We will also expand on the song’s theme, which is how subcultures (and “scenes”) operate. Finn is, in my opinion, the greatest lyricist working today (not the greatest living lyricist, that’s still Dylan). I’ve written about about Finn before here, and here.

Craig Finn himself has commented on this song and says that “It’s Never Been A Fair Fight”:

“Is about the extreme difficulty of staying true to the rigid rules of a subculture as you get older. The character in the song revisits an old peer and finds struggle and disappointment in the place he left behind.”

In this case, the narrator had been part of the punk/hardcore scene in the 1980’s and 1990’s, has left the scene, and reflects on his time there and what it meant as he meets his old friend—and we suppose former lover—Vanessa. I’m not sure I understand the entire chronology of the song, as it engages in some apparent time jumps that can be a little hard to follow. Overall however, it is pretty clear what the song is about.

The opening verse sees the narrator (let’s call him C., because while we will grant Finn the understanding as an artist that his characters are characters, in this case the song feels pretty autobiographical) checking in with Vanessa. The song opens in the present day.

Finn has C. meet her “right in front of her building,” Vanessa “vague in taste and drowning,” telling him she’s “got a new man…in a new band,” and “they’ve got a new sound.”

We get the impression that C. has been out of the scene for a while, while Vanessa is very much still in it: new man, new band, new sound, same old place. Vanessa’s man, we assume, is in a hardcore band, and I believe it is the case that Finn came up through the hardcore scene before forming his first band Lifter Puller. Lifter Puller is not a hardcore band, and I don’t know if Finn was actually in a hardcore band or just in the scene.

Then comes one of Finn’s perfect little deadpan truths. C. shrugs that “hardcore’s in the eye of the beholder,” a funny line for a number of reasons (it also reminds me of the classic David Berman line: “punk rock died when the first kid said / punk’s not dead.”) The humor hits because it’s both self-aware and scene-aware.

After C. recalls his “broken heart from 1989,” Finn pivots the timeline. The song shifts back—back to when C. was attending hardcore shows, hot and sweaty, elbows in his eyes. The chronology bends, but the emotional logic stays firm.

Vanessa says there are “threads that connect us,” and “flags and wars we should never accept.” Angelo’s off seeing “snakes in the smoke” from someone’s cigarette. And Ivan? He isn’t concerned at all — for him it’s mostly just about “what you wear to the show.” C. admits he “heard a song…on the radio” that he liked, which we can assume violates at least one of Vanessa’s unwritten rules.

Finn is an absolute master of sketching characters in just a line or two. Here, he uses a sort of pointillistic approach to introduce us to two additional members of the scene, Angelo and Ivan. With just a few short verses we already understand a great deal about “the scene.” Here is what we can deduce:

i) All four members of the scene have very differently valenced loyalties. Put another way, they want different things from it. Vanessa is a purist; for her being part of the scene is like being part of an tribe, an army, and we take her to be a fierce protector of the in-group/ out-group aspects that tend to arise in subcultures. Angelo, it seems, is a little out there; he’s seeing snakes in the cigarette smoke and probably not all that interested in the ultimate nature or meaning of the scene. Ivan likes the t-shirts and jeans, likes the look. He’s not a purist either. And C., well he likes a little pop music, an inclination we assume is strictly verboten for folks like Vanessa.

ii) Probably because of the differences in ideas and ideologies between the scene members, C. sees things coming to an end, both with the scene and between he and Vanessa. Here we are reminded of the difficulty of keeping any kind of group together, whether a scene, a band, or just a group of friends. Everyone knows the feeling of having a group of friends who tell each other they will be tight forever, however life doesn’t usually work that way. The best film about this dynamic is Whit Stillman’s Metropolitan, which depicts a young group of friends in Manhattan who come together and then slowly, but inevitably, come apart over the course of a winter. There is a great moment in Metropolitan where the main character, Tom, looks around and realizes the scene is dead. Where did it go? It was here one day, gone the next. Scenes are like that, and this is what Finn is writing about.

iii) The inherent differences between people which make keeping the scene together are also something that Finn celebrates to a certain extent I think. One of the most salient features of Finn’s writing is his compassion. Finn has compassion for Angelo and his snakes, Ivan and his jeans, and for Vanessa, in all of her rigidity. As of the time of the song we know for sure that Vanessa is still in the scene and C. is not. I guess that neither Angelo nor Ivan is still around, however if only one of them is my money’s on Angelo, if he’s still alive.

Through the course of my own life, I have been involved, for a shorter or longer time, with a variety of subcultures. One category of subculture that I have frequented is what we could broadly call “new age.” My explorations of this category have been reasonably extensive. Back in my early 20s, I was involved for about 4–5 months with a Tibetan Buddhist group back in Washington State. I would get up at 4 AM, drive an hour across town to a beautiful old house on the hill, and meditate with the folks there. This group also organized some outings, such as mountain hiking.

I enjoyed the group and the meditation. The group leader, a slightly older woman who was lovely, asked me to pay like 6 dollars for a little book with chants in it, which I did. There was a total cross-section of people in the group of different ages and backgrounds, and all in all I liked it there. However, I peeled off from the group after a time for reasons very similar to those discussed by Finn. There were two specific things that led to me leaving. The second I’ll discuss a little later. The first was one day I was chatting with one of the members on the street outside after meditation. He was telling me how his daughter used to play chess, however he would no longer allow her to do so because it was interfering with her studies of Tibetan Buddhism. “There’s just not enough time,” he told me.

I had talked with this guy before and he was a perfectly nice guy, but I didn’t agree with his approach. I felt, in fact, that it was bad action. Now, I understood that people joined the group for different reasons and had different levels of investment. I was not looking to become a Tibetan Buddhist or anything—I was just “checking it out.” To circle back to Finn, the valence gap between this fellow’s take on the subculture and my own was vast, and his entire approach turned me off. This was the first step in my deciding to leave.

The next three verses of “It’s Never Been a Fair Fight” see C. trying to keep the door open to Vanessa even as he edges out of the scene. He wants to meet her and if she agrees he will know that she like him feels that “punk is not a fair fight.” Finn doesn’t say, but I’m guessing Vanessa doesn’t show.

If things change quickly/ just remember I still love you/ and I’ll circle ’round the block tonight/ between 9 and 10 o’clock tonight

If you’re still standing here, I’ll take that as a sign/ that you agree it was a sucker punch/ punk is not a fair fight/ it’s never been a fair fight

We said there weren’t any rules/ but there were so many goddamn rules/ we said that they’d be cool/ but then there were so many goddamn rules

Verse VII is the hinge-point of the song and basically its thesis. Finn’s point is straightforward: the appeal of the scene is the potential for freedom, exploration, rebellion, however once inside the subculture C. finds himself increasingly hemmed in by the strictures of that culture and the requirements necessary to remain within it. The very thing that drew C. to the subculture (flight from an over-determined social reality) is that thing that ultimately drives him away. “It’s Never Been a Fair Fight,” appears in two versions on All These Perfect Crosses; the main version is horn driven and upbeat, and there is also an acoustic version. On the main version, Finn, realizing perhaps that the repeated line is a bit poetically unorthodox, spits out a laugh on the “then” in “but then there were so many goddamn rules,” and in the process underlines the centrality of the sentiment to the song as a whole. It’s a great verse, and one which tells us something fundamental about C.’s nature: he likes the action, and as such needs to be free to pursue it wherever it may be. Action is not limited to the Minneapolis hardcore scene, after all.

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The Adventures of the Thin Man and Andrea Available Now!

Well everyone, today is the day. My first novel, The Adventures of the Thin Man and Andrea is now available on Amazon and wherever books are sold.

This one took a while—written in fits and starts, in bars and hotel lobbies here in Kyoto—but it finally found its shape. More than anything, today I just want to thank all the readers of The Kyoto Kibbitzer, wherever you hail from; I’ve always thought of this as an ongoing conversation, and a lot of this book grew out of that exchange.

If you do pick it up, I hope you enjoy the ride—and if it lands for you, a quick review on Amazon would mean a great deal. Thank you, as always, for reading.

Matt

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On The X-Files: The Paranoid Style of 1990s Television

Note: This reflection comes out of a long-standing fascination with The X-Files, one of the most distinctive television shows of the 1990s. When it first aired, the series managed to occupy a strange and compelling middle ground between science fiction, horror, conspiracy culture, and something closer to philosophical inquiry. Week after week the show asked the same unsettling question from slightly different angles: what if the world is not quite as stable or intelligible as we assume?

What made the series especially effective was the dynamic between Fox Mulder and Dana Scully. Mulder represented the pull of belief, intuition, and pattern-seeking; Scully stood for skepticism, evidence, and scientific restraint. The tension between those two orientations created a kind of philosophical engine that powered the show for many seasons.

The major episode discussed here is one of the early “mythology-adjacent” stories that sits near the boundary between the show’s monster-of-the-week format and its deeper conspiratorial arc. Watching it again years later, what stands out is not only the eerie storytelling but also the way the series captured a particular cultural mood of the 1990s — a time when technology was expanding rapidly, institutions were increasingly distrusted, and the possibility of hidden systems operating beneath the surface of ordinary life felt strangely plausible.

In that sense, The X-Files was never just about aliens or government cover-ups. It was about uncertainty itself — the uneasy space between explanation and mystery.

Epigraph:

“Autorerotic asphyxiation is not a pleasant way to go, Mr. Mulder.”

Clyde Bruckman, The X-Files

The X-Files is my second favorite television show of all time, behind only The Wire, and it’s not close.

That may sound like a bold claim given the sheer amount of television produced over the past thirty years, but for those of us who came of age in the 1990s the show hit a nerve that very few cultural artifacts ever have. It wasn’t just entertaining. It was atmospheric. It was unsettling. It felt like it was plugged directly into the cultural nervous system of the time.

To understand why, you have to begin with a simple generational fact. I was born in 1974, just eleven short years after the assassination of John F. Kennedy. That event cast a shadow that lingered for decades. My parents’ generation and my grandparents’ generation were deeply scarred by it in ways that people my age never fully understood. Something in the national psyche broke that day. Trust in institutions never really recovered.

Historians later described this cultural mood as “The Paranoid Style of American Politics,” borrowing the famous phrase from the essay by Richard Hofstadter. Whether one agreed with Hofstadter or not, the phrase stuck because it captured a very real undercurrent in American life: the suspicion that unseen forces were operating behind the scenes.

The genius of The X-Files was that it leaned directly into that atmosphere. It didn’t treat paranoia as pathology. It treated it as narrative fuel.

Discovering the Show

I was an early adopter.

The show premiered in 1993, and by 1994 I was already watching it in the dorms at Hamilton College with a group of friends. If possible we’d get a little baked first, which in hindsight may have been perfect. The X-Files is a show that rewards slightly altered states of perception.

At first it was something of a cult discovery. A few people watched it religiously while others barely knew it existed. But by the time the second and third seasons rolled around it had become a communal ritual. Thursday nights meant Mulder and Scully.

The chemistry between the leads was immediately apparent.

David Duchovny and Gillian Anderson had what we would now call “shipping chemistry,” although that term didn’t really exist yet. We simply knew that something electric was happening on screen. The characters worked because they embodied opposing ways of understanding the world. Mulder believed everything. Scully was more skeptical. Between them the truth hovered in an unresolved middle ground.

The show was also disciplined enough to hold that tension for years. In an era before streaming algorithms and social-media speculation, viewers waited week to week to see how the relationship evolved.

Hovering over them was their boss, the enigmatic Walter Skinner. For several seasons it was impossible to tell whether Skinner was helping Mulder and Scully or quietly managing them on behalf of darker forces. That ambiguity was one of the show’s greatest pleasures.

In a delightful twist of pop-culture irony, the actor Mitch Pileggi was at one point named TV’s Sexiest Man by a glossy magazine. Which is hilarious when you remember that Skinner is essentially a bald FBI bureaucrat in a gray suit. Such was the cultural power of the show.

The Smoking Man

Then there was the figure lurking in the shadows.

The Cigarette Smoking Man is one of the great villains in television history. Played with eerie understatement by William B. Davis, he appeared whenever the conspiracy thickened.

He looks exactly like the kind of man who would be at the center of a decades-long government cover-up. Three packs a day. Cheap cologne. A lingering Jameson hangover. The sense that he spends most of his time in dim Washington parking garages and windowless offices and only emerges from his crypt when the conspiracy requires it.

It’s a performance so physical that you can almost smell the character through the screen.

Three Essential Episodes

Every long-running show has defining episodes, and The X-Files produced dozens. But three in particular illustrate what made the series so special.

The first is the pilot itself, which introduces Mulder investigating mysterious disappearances in the Oregon woods. A key moment occurs when the agents experience missing time on a dark forest road. The scene establishes the tone immediately: eerie, ambiguous, and faintly plausible.

The second is Fallen Angel, an early classic that introduces the lovable conspiracy obsessive Max Fenig. Max’s jittery paranoia captures the spirit of the show perfectly. When he remarks that “someone’s always watching, Mr. Mulder,” it feels less like dialogue than like a thesis statement.

The third is the masterpiece of dark humor, Clyde Bruckman’s Final Repose, written by the great Darius Morgan. In it, a weary insurance salesman named Clyde Bruckman discovers that he can foresee the exact circumstances of people’s deaths. Played beautifully by Peter Boyle, the character delivers a hilarious and oddly touching performance. It is Bruckman who also delivers the immortal line that also gives us our epigraph: “Autorerotic asphyxiation is not a pleasant way to go, Mr. Mulder.” Run roh. Take that belt off Fox baby.

What makes the episode remarkable is that it gently mocks the show’s own hero. Mulder spends the entire series searching for hidden meaning in the universe. Clyde Bruckman, by contrast, believes life is largely arbitrary and tragic.

His prediction of Mulder’s death—immortalized in the epigraph above—is both absurd and strangely profound. It’s also a sign that by Season Three the show had gained enough confidence to poke fun at itself.

When the Mythology Expanded

Like many successful serialized shows, The X-Files eventually struggled under the weight of its own mythology. One of the central narrative engines involved Mulder’s missing sister, Samantha Mulder. Early on, the mystery added emotional depth to Mulder’s obsession with the paranormal.

But as the seasons progressed the storyline became increasingly convoluted. Samantha might have been abducted by aliens, or replaced by a clone, or transformed into something else entirely. Meanwhile the conspiracy expanded to include frozen alien ships in Siberian ice, shadowy government syndicates, and the infamous black-oil virus that seemed capable of possessing human hosts.

At a certain point the mythology began to chase its own tail.

Then, as the final blow, David Duchovny left the show. Gillian Anderson remained excellent, but The X-Files was always fundamentally a two-hander. Without Mulder and Scully together the balance of the series shifted in ways it never fully recovered from.

Why It Still Matters

And yet, for all the narrative tangles of the later seasons, the early years of The X-Files remain extraordinary television.

The show captured a very particular moment in cultural history: the twilight of the pre-internet era, when conspiracy theories spread through late-night radio programs, photocopied newsletters, and whispered conversations rather than social media feeds.

It was a time when the idea that powerful institutions might be hiding enormous secrets still felt plausible rather than merely exhausting.

For a few seasons in the 1990s, Thursday nights belonged to the weirdest, smartest, most paranoid show on television.

The truth, as Mulder kept reminding us, was out there

Dedication

For Dana and Fox. You know we still want to know what went down in that motel room baby.

Note: If you enjoyed this essay you may also enjoy the two essays below, both of which, in different ways, take up themes of intrigue and mystery.

The Thin Man in Singapore Part I: Washing Ashore
Are There Aliens In Our Oceans? An Objective Investigation
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On Some Meetings and Close Encounters with Musicians II

Note: This is the second piece in our series “On Some Meetings and Close Encounters with Musicians.” You can find the first installment here.

The encounters described here span more than thirty years and several cities — from a first arena concert in Pullman, Washington in 1991 to small club shows in Cambridge, Osaka, and Kyoto over the decades that followed. As with many memories of live music, the exact setlists and dates blur, but the rooms themselves — the sounds, the atmosphere, the strange and fleeting meetings between artists and audiences — remain vivid. These sketches attempt to capture a few of those moments as they were experienced at the time.

Epigraph

No fears alone at night she’s sailing through the crowd

In her ears the phones are tight and the music’s playing loud

— Dire Straits, “Skateaway”

Live music produces strange meetings. Sometimes you meet the musicians themselves. More often you meet a moment — a room, a sound, a feeling that sticks with you for decades while entire years of ordinary life quietly disappear.

Here are a few such encounters.

I. Initiation

My first real concert was the On Every Street tour in 1991.

The band was Dire Straits, the venue was Pullman, Washington, and the company was the usual Spokane crew: Seth, Innes, Kelly.

I was the biggest fan in the car by far. The others liked the band well enough but I was the one who had studied the records, who knew the guitar parts, who was ready for the moment when the lights dropped and the first notes hit the arena. This was the On Every Street tour, which turned out to be their final record.

They played everything: Money for Nothing, Walk of Life, Sultans of Swing. It was a great show, and one of their last before retirement, though at the time I had no real way to judge such things. It was simply enormous — lights, volume, spectacle. I bought the black and blue tour shirt and wore it for five years.

At the time I thought concerts were supposed to be like that: huge, polished, and far away.

I would later learn otherwise.

II. Revelation

Several years later, during the Hamilton years, I saw Red House Painters at the Middle East in Cambridge.

I went with Ian. The room was small, maybe a few hundred people at most. Nothing about it resembled the arena in Pullman. And then, near the end of the set, Mark Kozelek began playing “Little Drummer Boy.” It lasted nine minutes. You could hear a pin drop in the room.

No spectacle. No lights. Just absolute concentration from everyone present. When the final notes faded the silence lingered for a moment before the applause came.

Afterward Ian and I drove back toward New York through the cold night with the windows cracked open, heaters flying out into the darkness, and Hell’s Ditch blasting through the car stereo to keep us awake.

That was the night I realized concerts could be something else entirely.

III. Chaos

Not every show produces reverence.

I once saw The Fall with Ian as well. The band’s leader, Mark E. Smith, seemed to be operating in his traditional mode of total hostility. The set was short — twenty-eight minutes by my estimate. Ian later checked the official record and insisted it was forty-three. Either way it felt brief and volatile. Smith barked into the microphone, glared at the band, and treated the entire enterprise with the air of someone barely tolerating the existence of the audience.

Which, to be fair, was exactly what many people had come to see.

IV. Theatre

The strangest performance I ever witnessed may have been Cat Power at Club Quattro in Osaka.

The evening began badly. An opening act — a woman in what appeared to be a fairy costume — sat at the piano and played for what felt like an eternity. Forty-five minutes at least. Perhaps longer. By the end of it the audience was openly confused.

Then Cat Power appeared.

Or rather she refused to appear in the conventional sense. Instead of remaining on the stage she wandered through the venue with a handheld microphone, singing and rapping while walking amongst the crowd, occasionally placing an arm around a patron or leaning against the bar.

At one point she came right up to where I was standing near the back rail and sang a line or two before drifting off again into the room.

The entire show felt less like a concert than a piece of improvised theatre.

V. Ritual

A few years later I saw Damo Suzuki at Club Metro in Kyoto. Damo had once fronted the legendary German band CAN, but this night bore no resemblance to those recordings. Nothing recognizable from the catalog appeared. And here he stood, just a few feet away from the audience with long black-and-grey hair flowing, bellowing and chanting over a constantly shifting improvisational band.

It was less a performance than a ritual.

Damo passed away not long ago. RIP and prayers up. I’m grateful I saw him when I did.

VI. Canada Night

Not all memorable shows are mystical.

Sometimes they’re simply loud.

One such evening occurred at Club Quattro in Osaka when Broken Social Scene and Death From Above 1979 came through town.

The Canadian ambassador was present and delivered a brief speech before the set explaining that Death From Above 1979 represented a fine example of Canadian enterprise because they were “only two men making so much noise.”

The room was packed with Canadian expats and the atmosphere was celebratory chaos. The ambassador was probably correct.

VII. Breakdown

Not every concert goes well.

I once saw Bonnie ‘Prince’ Billy at the small Kyoto venue Taku Taku. Something had clearly gone wrong with the lineup. The guitarist appeared to be brand new and could barely navigate the chords.

Will Oldham tried to push through but quickly grew frustrated and began openly calling the guitarist out from the stage. It was uncomfortable for everyone involved.

The show never recovered.

VIII. Redemption

Fortunately the story has a better ending.

Some years later I saw Bonnie “Prince” Billy again, this time at the beautiful Kyoto venue Urbanguild and everything worked great. Low benches and tables filled the room, Heartland beer bottles glowed green under the lights, and the band played a relaxed, confident set drawn mostly from the Bonnie “Prince” Billy catalog with a few Palace songs mixed in.

Opening the evening was an instrumental group called Bitchin Bajas whose sound reminded me faintly of early Phosphorescent if Phosphorescent had chosen to make instrumental records. After the show I found myself talking with three members of the band while they drank beer and ate fries. They were humble, friendly, and slightly surprised that anyone in Kyoto knew who they were. We talked for a while about touring and the constant challenge of trying to make a living as working musicians. Eventually the conversation drifted off and the room began to empty.

The music was over. The musicians were just people again, finishing their drinks and preparing to move on to the next city. And that, in the end, may be the most interesting encounter of all

Dedication

For live music fans everywhere. My true people. I love you baby.

Note: If you enjoyed this essay, you may also enjoy the essay below on the four time I met Yo La Tengo. Happy reading!

On the Four Times I Met Yo La Tengo
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On The Dubious Anna Delvey

Note: This essay reflects on the curious cultural figure of Anna Delvey, whose rise and fall in the New York art and social scene became one of the stranger morality plays of the late 2010s. Delvey—born Anna Sorokin in Russia—gained notoriety for presenting herself as a wealthy European heiress while attempting to secure loans and social capital for an ambitious but largely imaginary cultural venture known as the Anna Delvey Foundation.

The events described here draw on widely reported elements of the case: Delvey’s years moving through luxury hotels in Manhattan, her efforts to obtain financing for a private art and social club, the unraveling of her financial claims, and the now-famous trip to Dubai in which a friend—later a magazine writer documenting the experience—was left responsible for an enormous hotel bill after promised funds failed to appear.

The piece does not attempt investigative reporting. Instead, it approaches the story in a spirit of cultural anthropology. Cities like New York have always attracted individuals engaged in various forms of self-invention. The line between ambition, performance, exaggeration, and outright fraud can sometimes appear only after events have run their course. Delvey’s story is compelling partly because it dramatizes this thin boundary in unusually vivid form.

If the tone here sometimes drifts toward sympathy rather than condemnation, that is intentional. Many urban cultural scenes—especially art worlds—operate on the energy of strivers who are, in one way or another, attempting to become something slightly larger than their present circumstances allow. Most of them eventually succeed or quietly disappear. A very small number, like Delvey, collapse in public.

Their stories reveal something not only about themselves, but about the environments that briefly believed in them.

Epigraph

“For all the crazy people who can never get it right.”
— Drugstore

I. The Entrance

There is a certain kind of person who arrives in a city not merely to live there but to declare themselves into existence. Cities like New York attract them the way bright lights attract moths. They arrive with luggage, ideas, clothes that signal belonging, and an almost reckless confidence that the future will eventually arrange itself around their intentions.

Anna Delvey was one of these people.

When she appeared in the New York art scene, she seemed to possess the basic ingredients required for entry into that peculiar ecosystem: style, confidence, and an air of European mystery. She wore expensive-looking dresses and shoes. She wore aa lot of make up and had her hair done at expensive salons. She seemed for a while to ooze money. She spoke casually about ambitious cultural projects. She moved through hotels and restaurants as if she had always belonged to that world. In New York, that is often enough.

The city runs on confidence performances. Every ambitious young person who arrives there is, in some sense, performing the life they intend to have. The art world especially is full of people who are not yet what they claim to be but are working very hard to become it.

Delvey fit into that theater perfectly.

II. The Vision

The striking thing about Delvey was that she didn’t simply want to attend the art scene. She wanted to build something inside it. Her idea was the Anna Delvey Foundation: a kind of private cultural club and exhibition space in downtown Manhattan. It would combine gallery spaces, social rooms, events, artists, patrons, and the atmosphere of a private cultural salon. A place where the city’s creative and wealthy classes might gather.

The plan was grand. But it also had a strange plausibility. New York is full of institutions that began with the ambition of a single person who simply decided that something should exist and then spent years convincing others to believe in it.

Delvey spoke about the project with total conviction. She behaved like someone who already possessed the financial backing required to make such a thing happen. And because she behaved that way, many people assumed the money must exist somewhere.

This is one of the basic mechanics of social confidence. If someone carries themselves like a person whose financial arrangements have already been verified by someone else, most people will not ask too many questions.

III. Hotels

Hotels played a central role in the Delvey story.

Luxury hotels are perfect environments for people living inside ambitious performances. They operate on the assumption that their guests are legitimate. The bill will eventually be settled. The credit line exists somewhere. The guest’s presence itself is treated as evidence of solvency.

Delvey floated through some of New York’s most expensive hotels as if she were simply another wealthy European visitor temporarily residing there while arranging various cultural affairs. The lobbies, the restaurants, the rooms—all of it provided a stage set that reinforced the story she was telling.

Hotels also create a particular social atmosphere. Everyone is temporarily suspended between identities. People are traveling, negotiating, arriving, leaving. It is a place where someone can exist slightly outside the ordinary structures of verification.

For a while, the performance worked.

IV. The Father

Like many figures who construct elaborate new identities, Delvey carried with her a somewhat murky origin story.

She spoke of family wealth. Of connections. Of a background that seemed to hover somewhere between Russia and Germany, between modest beginnings and more glamorous narratives.

Her real childhood was more ambiguous. Her father had worked as a truck driver and later operated a heating and cooling business. It was a respectable, ordinary life. But it did not contain the European aristocratic wealth that sometimes appeared in Delvey’s stories.

This kind of ambiguity is not unusual among people attempting radical self-invention. The past becomes something flexible, something that can be rearranged slightly in order to support the person one intends to become.

In cities like New York, such reinvention is practically a tradition.

V. Dubai

The most extraordinary episode in the Delvey saga took place far from Manhattan, on a trip to Dubai. Delvey traveled there with a friend—a magazine writer who was documenting the glamorous world that Delvey seemed to inhabit. The trip was meant to be luxurious: private villas, elaborate dinners, the kind of extravagant travel that confirms a person’s social status.

For a few days everything unfolded according to the script. And then the bill arrived. The charges for the trip reached roughly $60,000. Delvey’s payment arrangements suddenly failed. The promised wire transfers did not appear. The hotel demanded settlement.

And the friend—the magazine writer who had been invited along for the ride—found herself responsible for the enormous bill. So Delvey left her there. Super bad business Anna baby.

It was a moment that perfectly captured the strange mechanics of confidence artistry. The performance works right up until the moment when reality insists on payment.

Someone, eventually, must pay the bill.

VI. Collapse

Once the financial machinery began to fail, the unraveling accelerated. Banks wanted documentation. Hotels wanted payment. Institutions that had briefly entertained the idea of supporting Delvey’s foundation began to ask more detailed questions about the supposed trust fund that would finance it.

The answers did not exist. The performance collapsed. Delvey was eventually arrested, tried, and convicted of fraud.

VII. The Strange Sympathy

And yet the Delvey story produced a strangely sympathetic public response. Perhaps it was because she had not simply been extracting money for luxury purchases. She had been trying, in her own improbable way, to create something. A cultural institution. A social space. A downtown hub for art and ambition.

The plan was impossible, but the ambition was recognizable. Many people—especially those drawn to cities like New York—understand the impulse to reinvent oneself, to construct a future through sheer force of belief. Delvey simply pushed that impulse far beyond the point where the arithmetic could sustain it.

VIII. Coda

In the end, the most interesting thing about Anna Delvey may not be that she fooled people. New York has always been full of people attempting improbable social performances. The interesting thing is that, for a moment, she came very close to building the life she imagined. And perhaps that is why stories like hers continue to fascinate us. They remind us that the line between visionary and impostor is often visible only in hindsight.

Dedication: For Anna baby (you’re hot BTW) and all the beautiful strivers out there. May your world-curated art spaces someday come true.