The Great Roast of Bill Simmons, The Podcasting GOAT

Note: Bill Simmons has many gifts, but none more enduring than his ability to take a perfectly good idea and turn it into a totalizing worldview. Chief among these is his obsession with “who gets the keys,” a concept that began as a useful shorthand for late-game NBA hierarchy and has since metastasized into a governing principle for all human activity. In Simmons’ hands, the question is no longer who closes Game 7, but who closes anything: marriages, movies, bands, revolutions, and possibly even the Enlightenment. It is a framework so elastic that it explains everything and therefore, in a quiet and almost admirable way, explains nothing. Yet Simmons returns to it again and again, like a man who has discovered fire and insists on using it to cook every meal. The result is less analysis than ritual: a familiar incantation that reassures both host and listener that control exists, that someone always has it, and that identifying that person is the highest form of understanding. Whether this is insight or compulsion is an open question, but in the meantime, Simmons has the keys—and he’s not giving them back.

I. The Obsessive With the Keys

Bill Simmons is a strange and singular figure in American media, a man whose greatest innovation may have been to take the interior monologue of a slightly obsessive sports fan and publish it wholesale, unfiltered, and then slowly convince an entire industry that this was not only acceptable but essential. He is not quite a journalist, not quite a commentator, and not quite a comedian, but rather a hybrid form: a “Sportish Guy,” as Cousin Sal once put it, who treats every game, every movie, and every stray anecdote as part of a single, ongoing argument about how the world works. Central to that argument is his enduring fixation on control, on agency, on the question he returns to again and again with the devotion of a man checking the locks before bed: who gets the keys?

It is tempting to dismiss this as a bit, and in some sense it is, but like all of Simmons’ best bits, it has metastasized into something larger and more revealing. What began as a useful shorthand for late-game NBA hierarchy—who has the ball, who takes the shot—has expanded into a general theory of human behavior. Quarterbacks have the keys. Movie characters have the keys. Entire bands, dynasties, and historical figures are evaluated based on whether they had, lost, or never quite secured the keys. That Mark Sanchez could, for a brief and inexplicable moment, be discussed in these terms tells you less about Sanchez than it does about Simmons’ commitment to the framework. He does not particularly care if the fit is perfect. The system must be applied.

This is what makes Simmons both compelling and faintly ridiculous. He is, at heart, a “who’s on my team” guy, a loyalist who rewards proximity, familiarity, and shared history, sometimes to a fault. Former colleagues have occasionally noted that he can cool on people once they leave his orbit, a tendency that reads less as malice than as a kind of emotional sorting mechanism: you are either in the ecosystem or you are not. Some, like Kevin O’Connor, speak warmly of early generosity—gifted shirts, guidance, a foothold in Los Angeles when money was tight. Others have been less charitable, and the occasional critique, including a much-circulated piece in The New York Times, has tried to frame Simmons’ blind spots, particularly around race, as more systemic. These critiques are not wholly without merit, but they often feel slightly overdetermined, flattening a personality that is better understood as idiosyncratic rather than ideological. Simmons himself tends to respond not with grand rebuttals but with motion—hiring voices like Van Lathan, insisting, plausibly, that such moves were already in progress, and continuing on as if the conversation will resolve itself over time.

There is also, undeniably, an ego in play. Simmons has built an empire—Grantland, then The Ringer—largely on the strength of his own voice, and he is not shy about asserting it. Stories persist, as they do in any media ecosystem, including the long-running rumor that he played a role in Magic Johnson’s exit from NBA Countdown, a claim Simmons has repeatedly and emphatically denied. More verifiable is the moment that effectively ended his ESPN tenure: a live broadcast of NBA Countdown in which, after a colleague spoke at length, Simmons leaned in with heavy, unmistakable sarcasm—“Oh, is it my turn to talk now?”—a line that was funny, revealing, and, in the context of corporate television, fatal. It was the voice of the columnist breaking through the format, the irrepressible instinct to comment on the comment, to seize the keys even when the structure said otherwise.

What makes Simmons unique, and worth writing about at all, is that these contradictions—generous and insular, insightful and reductive, earnest and performative—are not bugs but features. He is a weird obsessive who has turned his obsessions into a career, and in doing so has given us a language that is at once clarifying and absurd. He loves the game, he loves the conversation around the game, and above all he loves the feeling that somewhere, in any given moment, someone has the keys.

II: The Bits That Ate the Brain

If the keys are the theory, the bits are the practice. Simmons has always understood that repetition is power: say something often enough, with just enough conviction, and it graduates from joke to canon. Thus “greatest stickman,” a phrase that should have died in a driveway, becomes a legitimate category, and suddenly Burgess Meredith is being floated as an all-timer. “Sal, Sal, BM was the greatest stickman of all time. Every lady wanted a ride.” It is ridiculous, obviously, but also irresistible. The specificity disarms you. The confidence sells it. The framework expands.

This is the Simmons trick: take a private-language riff and run it until it becomes a public one. It does not matter that no one else has ever considered ranking “stickmen.” What matters is that Simmons has, and that he will return to it, again and again, until you find yourself half-convinced that you, too, should have an opinion. It is analysis as inside joke, inside joke as analysis.

III. The Ecosystem

No system survives without a supporting cast, and Simmons has assembled one of the most durable in podcasting.

There is Cousin Sal, the indispensable counterweight, quicker and often funnier, whose primary function is to puncture Simmons at exactly the right moment. The Vegas trips are their shared masterpiece: two grown men insisting, year after year, that this time they will behave differently, and then not. Simmons, improbably, claims that he only smokes in Vegas. No one believes this. The morning-after pod is the payoff—hungover, frayed, the truth leaking out in fragments. “I only had three cigarettes last night,” Simmons offers. Sal, without missing a beat goes: “Yeah, more like three lighters.” It is the kind of line that ends the discussion because it cannot be improved.

There is Joe House, lawyer by day, chaos agent by night, who turns every appearance into a small act of self-destruction. “House Eats” remains a high-water mark: an adult man consuming Chinese food until he vomits, captured and distributed as legitimate sports media content. It should not work. It works perfectly. Drunk House—slurring, swearing, denouncing Daniel Snyder with operatic intensity—is not a bug but a feature. Simmons does not rein him in; he amplifies him. The ecosystem thrives on this permissiveness.

And then there is Nephew Kyle, the quietly essential, publicly baffling producer whose qualifications are, at best, opaque. The nepotism is acknowledged, even embraced. Simmons does not pretend otherwise. He does not have to. The show goes on. The levels are sometimes off. The energy is always on.

IV. The Interviews: High Risk, High Variance

Simmons as interviewer is a study in range. At his best, he is disarming, patient, and genuinely curious, capable of extracting moments that feel both candid and consequential. His conversation with Al Michaels is a case in point: Michaels, relaxed, recounts the day of the O.J. chase, including the now-legendary call-in where a supposed eyewitness punctuates his tip with “Baba Booey.” The co-host takes it seriously. Michaels does not. “It’s a joke, dude,” he essentially says, and in that moment you see the difference between professionals. Simmons knows enough to step back and let the story land. It is radio as it should be: a master talking, a host listening.

The interview with John Skipper is another apex moment. Post-ESPN, Skipper speaks with a level of openness that borders on the shocking—cocaine use, morning routines, the normalization of behavior that would end most careers. Simmons guides rather than pushes, and the result is a “huge get,” the kind of conversation that justifies the entire enterprise.

At the other end of the spectrum sits the Denzel Washington interview, a minor classic of mismatch. Washington arrives as if for one kind of conversation; Simmons is clearly expecting another. The opening is awkward, the rhythms off. To his credit, Simmons does not retreat. He leans in, tries to find common ground, and eventually does, or at least something like it. It is not a triumph, but it is revealing: the limits of the format, the limits of the host, the persistence of the effort.

V. Homerism as Method

Simmons’ greatest cultural contribution may be the legitimization of homerism. Before him, fandom was something to be managed, disclosed, occasionally apologized for. With him, it becomes the point. He is, unapologetically, a Boston guy: the Boston Celtics are not just a team but a lineage, a narrative, a near-mythological entity anchored by figures like Larry Bird, whose legend grows incrementally with each retelling. The takes are, at times, outta control. They are also, in their way, coherent. Simmons is not pretending to objectivity. He is offering a perspective, and trusting that the audience will meet him there.

This approach extends beyond basketball. Baseball, once a central obsession—AL keeper leagues, granular analysis—fades over time, dismissed as too long, too slow, no longer aligned with the rhythms of his life or his listeners’. Basketball remains the core competency, the area where his knowledge is both deep and defensible. Everything else orbits around it.

VI. Family and Formation

The personal mythology is never far from the surface. Simmons’ father, a longtime Celtics season-ticket holder, is both character and audience, the origin point of the fandom that would become a career. The pride is evident, even when unspoken. The access—courtside seats in the 1970s—becomes part of the narrative, a credential as meaningful as any byline.

His mother, less present on the pod but frequently referenced, provides another axis: a love of movies, a different kind of cultural literacy that feeds into Simmons’ broader interests. The recurring mention of being a child of divorce functions as a kind of grounding note, a reminder that the voice, however confident, has origins in something more fragile. He seems, by most measures, to have come out fine.

VII. Drift and Discipline

As the empire grows—Grantland, then The Ringer, now under the umbrella of Spotify—Simmons changes in ways both subtle and obvious. He fades certain voices who no longer fit the evolving brand: Adam Carolla, once a regular presence, becomes less so; Michael Rapaport, similarly, drifts out of the rotation. The official reasons are varied—tone, fit, the simple passage of time—but the underlying dynamic is familiar. Simmons is, at heart, a “who’s on my team” operator. The team changes. The roster turns over.

And yet, it is hard to shake the sense that the affection remains. These are not clean breaks so much as quiet reassignments, the byproduct of a system that requires a certain level of control. Spotify money, corporate expectations, the need to maintain a particular tone—these exert their own pressure. The outta-control energy that defined earlier iterations of the pod is still there, but it is managed, channeled, occasionally held back.

VIII. The Countdown Moment

If there is a single scene that captures Simmons in miniature, it is the one that ends his ESPN tenure. On NBA Countdown, a colleague speaks at length. Simmons waits. And waits. And then, with a level of sarcasm that is both unmistakable and, in context, disastrous, he interjects: “Oh, is it my turn to talk now?” It is funny. It is honest. It is, within the rigid structure of live television, unacceptable.

He is removed not long after.

The moment endures because it reveals the core tension: Simmons the columnist versus Simmons the employee, the impulse to comment versus the requirement to conform. He cannot quite suppress the former, even when the latter demands it. He reaches for the keys, even when they are not his to take.


VIII. Conclusion

Bill Simmons is the GOAT podcaster, full stop, and it’s worth saying that clearly at the outset because we only roast the ones we love. Bill Simmons has given us an entire language—keys, stickman, Vegas nights, Sal lines, Drunk House—and if you’ve been along for the ride, those bits don’t wear out, they compound. They get funnier with time, richer with context, a kind of private shorthand that becomes, almost accidentally, a shared culture. You either hear “three lighters” and laugh immediately or you don’t, and if you don’t, there’s not much point explaining it.

This is part of what makes Simmons both beloved and, in certain circles, a little contentious. He has clearly made enemies—inside ESPN, across the broader media landscape, and occasionally among former employees—and while it’s easy to chalk this up to ego or looseness, the better read is that the looseness is largely performative. Underneath the hangout vibe, the teasing, the Nephew Kyle chaos and the Drunk House indulgence, there is a very real set of standards, and Simmons enforces them. He is, at heart, a “who’s on my team” operator, and the team matters. People drift out. Some of that isn’t pretty. Most of it, however, is consistent with how he’s always operated: loyal, selective, and ultimately in control of the room.

At the same time, there is a sense now that Simmons is, if not slowing down, then at least rounding off the sharper edges. He talks openly about retirement in a way he didn’t a decade ago, and you get the feeling that he is aware, at some level, of the limits of the bit. Will he be seventy-five, still ranking stickmen and assigning keys? It’s hard to see it. He’s a boss now, a central figure inside Spotify, with responsibilities that extend well beyond the pod. The insurgent has become the institution, and while the voice is still there, it’s necessarily more managed than it once was.

There’s also the simple fact that Simmons is no longer a writer in the way he once was, and he knows it. The old columns—the mailbags, the trade value pieces, the obsessive digressions—have given way to the pod, to conversation, to rhythm. He jokes that his fingers don’t work anymore, and like most of his best lines, it’s funny because it’s partly true. The Book of Basketball stands as the monument to that earlier phase: long, ambitious, slightly out of control in the best way, complete with the famous pyramid (Jordan at the top, Magic above Bird, a decision that still tells you everything you need to know about him). But the shift from writing to talking isn’t a decline so much as an evolution. Simmons was always more voice than text anyway. The medium finally caught up to the man.

If and when he does step back, what we lose is not just a podcast or a brand but something rarer: a genuinely original voice that bent an entire corner of the media world toward itself. Plenty of people analyze sports. Plenty of people talk about culture. Almost no one has managed to fuse the two into a single, durable, endlessly riffable system the way Simmons has. The keys, for all their absurdity, are real in that sense. He found them early, used them often, and built something that will outlast the bit itself.

And if he eventually decides to set them down, or even just hold them a little more loosely, it will mark the end of a run that, for all its contradictions, was unmistakably his.

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.

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.

3

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.

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…

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.

The Most Insane People of All Time: #3 Elizabeth Holmes (aka You’re Outta Control!)

Epigraph: 

“This is the dawning of the age of Aquarius…”

— Aquarius/Let the Sunshine In, The 5th Dimension

Elizabeth Holmes emerges in Silicon Valley with the full prodigy package: Stanford dropout, world-changing ambition, and a carefully constructed persona. She leans hard into the comparison with Steve Jobs — black turtlenecks, minimalist language, intense seriousness — and presents herself as the young visionary who will revolutionize medicine. The pitch behind Theranos is irresistible: hundreds of diagnostic tests from a single finger prick. Investors, politicians, and media figures line up. The board fills with heavyweight names including George Shultz, and the company’s valuation soars to roughly $9 billion. Holmes becomes, on paper, the youngest self-made female billionaire. It’s classic Silicon Valley moonshot energy — bold claims, secrecy, and belief outrunning reality.

The problem, as insiders begin to realize, is that the technology doesn’t work at all. Engineers and lab staff struggle to produce reliable results, while Holmes and her partner Ramesh Balwani continue presenting the system as revolutionary. The company begins quietly using conventional lab equipment while maintaining the illusion. Whistleblowers emerge, including Shultz’s own grandson, who raises concerns at significant personal cost. The leadership circles the wagons. Meanwhile, John Carreyrou of The Wall Street Journal begins investigating, encountering secrecy, evasive answers, and mounting contradictions. His reporting — later expanded into the book Bad Blood — becomes the turning point. The narrative collapses, regulators move in, partnerships evaporate, and the once-mythic startup implodes.

Legal consequences follow. Holmes and Balwani are charged with fraud, and after a long, high-profile trial she is convicted on multiple counts. She delays reporting to prison after becoming pregnant, later giving birth with partner Billy Evans. Eventually she begins serving her sentence in a minimum-security federal facility. Even there, the mythology lingers — supporters, critics, and observers debating whether she was a calculating fraud, a true believer, or some combination of both. The arc is striking: Stanford prodigy, Jobs imitation, $9 billion valuation, total collapse, and prison. Less chaotic than John McAfee, less creepy than Keith Raniere, but still unmistakably outta control — a billion-dollar story built on belief, performance, and a technology that never worked.

Steve Jobs represents the template Elizabeth Holmes tried to emulate. Jobs cultivated a minimalist aesthetic, black turtlenecks, product mystique, and a “reality distortion field” that persuaded investors, employees, and customers to believe in things before they fully existed. But the crucial difference is that Jobs ultimately delivered. From the original Macintosh launch in 1984 to the iPod in 2001 and the iPhone in 2007, Apple shipped real, transformative products. Jobs bent reality rhetorically, not technically; Holmes attempted to bend reality where physics and chemistry refused. The comparison highlights both the ambition and the failure — she borrowed the style, but not the substance.

Bernie Madoff represents the classic institutional fraud parallel. A former NASDAQ chairman, Madoff operated a decades-long Ponzi scheme through Bernard L. Madoff Investment Securities, promising steady returns that attracted elite clients, charities, and feeder funds. By the mid-2000s, billions were under management, including investments tied to major institutions and wealthy families. In December 2008, amid the financial crisis, Madoff confessed to his sons, was arrested, and the scheme collapsed, revealing losses estimated at roughly $65 billion in paper value. The deception persisted largely through reputation and trust — investors assumed competence because of his stature. Holmes operated similarly: prestigious board members, high-profile endorsements, and a narrative of inevitability masked a system that didn’t work. Like Madoff, she benefited from credibility cascading downward — once enough influential people believed, the illusion sustained itself.

Sam Bankman-Fried provides the modern startup-era comparison. Bankman-Fried founded the cryptocurrency exchange FTX in 2019, and within a few years it was valued at around $32 billion. He cultivated a quirky, disheveled persona and promoted “effective altruism,” pledging to donate vast sums to global causes. FTX attracted major investors including venture firms and high-profile endorsements, while its sister trading firm Alameda Research operated closely behind the scenes. In November 2022, liquidity concerns triggered a rapid collapse, revealing commingled funds and massive shortfalls. Bankman-Fried was arrested in December 2022 and later convicted in 2023 on fraud and conspiracy charges. The arc mirrors Holmes: meteoric rise, media fascination, complexity masking weakness, and sudden implosion once scrutiny arrived. Where Jobs built something real and Madoff ran a traditional financial fraud, Bankman-Fried and Holmes sit in the same modern category — startup mythology outrunning reality.

In the end, the most astonishing thing about Elizabeth Holmes is not just the scale of the deception but the audacity of it. How, exactly, did she think she was going to get away with it? Blood testing is not social media. It’s not software. It’s chemistry, biology, physics — things that eventually either work or don’t. Yet she and Ramesh Balwani kept pushing forward, covering, deflecting, and doubling down as the gap between claim and reality widened. That’s the outta-control element: the belief that charisma, secrecy, and prestige could override science indefinitely. At some point, the story had to collapse. But like many figures in this series, Holmes seems to have inhabited a gray zone between calculation and belief — part fraud, part self-hypnosis — which made the whole thing both more dangerous and more surreal.

Then there’s the broader cultural context, including the willingness of powerful people to buy in. Even Barack Obama publicly embraced the Theranos narrative early on, holding Holmes up as a symbol of innovation and entrepreneurial promise. Chump. In retrospect, it’s striking how easily the image worked: the black turtleneck, the calm intensity, the world-changing pitch. Smart people — very smart people — saw what they wanted to see. It’s a reminder that charisma plus narrative can override skepticism, especially when wrapped in Silicon Valley optimism. The episode becomes a cautionary tale: will future founders learn from this, or will the same hubris reappear in new forms? The myth of the visionary is powerful, and the temptation to believe in it hasn’t gone away.

The quiet hero of the story, meanwhile, remains the Theranos whistleblower — George Shultz’s grandson — who raised concerns when doing so meant alienating family, risking his career, and standing against a multibillion-dollar narrative. He saw that the technology didn’t work, said so, and held his ground. In a story dominated by hype, status, and belief, that kind of stubborn insistence on reality stands out. Holmes’s rise is outta control, her fall inevitable, but the ending belongs to the people who refused to play along.

Note: If you liked this piece, you may also like the other ones in out “You’re Outta Control” series.

When the Taxi Driver Loses the Plot: A Poem

Note: This poem is a reconstruction. The original version appeared briefly on my first blog, Classical Sympathies, sometime around 2010, and like many things from that early site it was eventually lost in the digital shuffle. What remains here is an attempt to recreate the spirit of the piece from memory.

The poem itself is a mash-up of two real taxi rides that somehow fused together in recollection. One took place in Adelaide, Australia, during a ride from a hotel to the airport where the driver became thoroughly disoriented and began looping through unfamiliar streets. The other occurred years later in Kyoto, somewhere north of Sanjo, when a similarly confused driver managed to transform a short ride into a wandering tour of the nighttime grid.

Over time the two rides merged in memory into a single universal experience: the moment when a passenger realizes that the person holding the wheel may no longer fully know where he is going.

The result is presented here, perhaps a little mythologized, as a small recovered relic from the early days of the archive — a lost classic of the wandering taxi ride.

The haunted sweating taxi driver
took another right,
the meter ticking bravely
in the middle of the night.

The city slid past sideways
in a crooked grid of light,
and every turn he promised
somehow made the journey slight.

The haunted sweating taxi driver
muttered to the wheel,
as if the streets were hiding
some essential missing deal.

A restaurant we’d passed before
returned into my sight,
which meant the haunted driver
had again chosen wrong from right.

The haunted sweating taxi driver
took another right,
and wiped his brow dramatically
beneath the yellow light.

Now when your taxi driver loses the plot
this could go on all night,
because the man who holds the wheel
is captain of your flight.

You sit behind his kingdom
like a mildly troubled guest,
while every wrong decision
slowly multiplies the rest.

The haunted sweating taxi driver
leans forward in his seat,
as though the road might whisper
some confession through the street.

The meter ticks its steady hymn
to time and mortal plight,
while hostage to the haunted man
who’s searching for the right.

The haunted sweating taxi driver
takes yet another right,
and somewhere in the city
dawn prepares its quiet light.

But we remain in orbit
of his navigational blight—

for when your taxi driver loses the plot
this could go on all night.

Note: If you like this poem, you may also like the poems linked below. Happy reading!

On Comebacks and Failed Comebacks V: Rod Blagojevich

Note: This essay concludes the small series “On Comebacks and Failed Comebacks.” The earlier pieces explored several very different kinds of returns: the moral vindication of Kofi Annan, the sly tactical persistence of Joe Nash of the Seattle Seahawks, the tragic artistic authenticity of Amy Winehouse, and the mythic public legend surrounding Muhammad Ali.


The story of Rod Blagojevich introduces a different category altogether: the shameless comeback.

Unlike the other figures in the series, Blagojevich’s return to public life does not depend on moral vindication, heroic persistence, or cultural myth. Instead it illustrates something more peculiar about contemporary politics and media. In an age of fragmented audiences and constant attention cycles, a disgraced figure may sometimes reappear simply by refusing to leave the stage.

Whether one sees Blagojevich’s re-emergence as comic, absurd, or oddly instructive, it provides a fitting final example for the series. Not every comeback is admirable, but each one reveals something about the strange ways public life allows stories to continue.

Not all comebacks are noble.

Some are heroic, like the moral vindication of Kofi Annan. Some are tactical, like the sly fourth-quarter returns engineered by Joe Nash of the Seattle Seahawks. Some exist somewhere between tragedy and authenticity, like the brief blazing career of Amy Winehouse. And some, like the legend of Muhammad Ali, grow into something close to myth.

But there is another type of comeback altogether.

The shameless comeback.

For that, it is difficult to find a more perfect case than Rod Blagojevich, the former governor of Illinois whose political career once appeared to have ended in spectacular disgrace.

The original scandal is by now familiar. In 2008 federal investigators revealed that Blagojevich had been recorded on FBI wiretaps discussing how he might profit from appointing a replacement to the U.S. Senate seat vacated by President-elect Barack Obama. The recordings were devastating. In one of the most memorable lines in modern American political scandal, Blagojevich described the Senate seat as something valuable that he was reluctant to give away for nothing.

The fallout was swift. Blagojevich was impeached and removed from office by the Illinois legislature. Later he was convicted on multiple corruption charges and sentenced to federal prison. For most politicians, this sequence would represent the end of the story.

Disgrace. Prison. Silence.

But American public life has always contained another possibility: the comeback powered not by redemption but by spectacle.

Even before his imprisonment, Blagojevich seemed instinctively drawn toward the theatrical dimension of his situation. He appeared on television talk shows, launched media interviews, and treated the unfolding scandal almost as if it were a strange kind of reality program in which he remained the central character.

His appearance on The Celebrity Apprentice, hosted by Donald Trump, felt less like an attempt to restore dignity than a recognition that modern politics and entertainment had already merged.

Then came the commutation.

In 2020 Trump commuted Blagojevich’s prison sentence, releasing him after several years behind bars. The decision itself was controversial, but the effect was unmistakable: the stage was suddenly open again.

And Blagojevich, to his credit—or perhaps to his creditlessness—walked right back onto it.

The most striking feature of his post-prison public life has been the absence of embarrassment. Many disgraced politicians attempt some form of contrition when they re-enter the public conversation. Apologies are issued. Lessons are discussed. A tone of humility is adopted.

Blagojevich chose a different path.

Instead he embraced a kind of shameless persistence, appearing in conservative media outlets, repositioning himself politically, and speaking about his case with the tone of someone who believes the whole episode was misunderstood or exaggerated. The ideological shift from Democrat to Republican was particularly striking, not because party changes are unheard of but because in Blagojevich’s case it seemed less like a conversion than a strategic recalibration.

It was, in other words, a comeback powered by the modern media ecosystem.

In an earlier era, a corruption scandal of this magnitude might have consigned a politician to permanent obscurity. But the fragmented media landscape of the twenty-first century offers a different possibility. There is always another audience somewhere, another platform, another narrative waiting to be constructed.

Blagojevich appears to understand this instinctively.

Which is why his story belongs in a series about comebacks, even if the comeback itself is of a peculiar variety. Unlike the moral return of Annan or the mythic return of Ali, Blagojevich’s version depends less on redemption than on endurance.

The secret of the shameless comeback is simple.

You refuse to leave the stage.

You keep talking. You keep appearing. You keep telling your version of the story until, slowly but inevitably, the scandal itself begins to blur into just another chapter in the larger spectacle of American politics.

In that sense Rod Blagojevich may represent a distinctly modern form of comeback: not heroic, not tragic, but theatrical.

And in the strange carnival of contemporary public life, theatrical persistence can sometimes be enough.

On Comebacks and Failed Comebacks III: Amy Winehouse

Note: This short piece reflects on the strange artistic tension that defined the career of Amy Winehouse: the way her extraordinary authenticity as a singer seemed inseparable from the personal instability that surrounded her life.

Winehouse’s music—especially the songs on Back to Black—felt at once timeless and painfully immediate. The sound drew deeply from earlier traditions of soul and rhythm and blues, yet the emotional directness of the lyrics was unmistakably modern. Few artists have managed to sound so rooted in musical history while simultaneously feeling so exposed to the present moment.

The song Rehab stands as the clearest example of this tension. Its humor, defiance, and vulnerability all exist in the same breath, making it one of the most distinctive pop recordings of the twenty-first century.

Like many listeners, I remember the late-2000s period—particularly around the Glastonbury era—when Winehouse was both an enormous star and visibly struggling. Watching those performances could feel uneasy, yet the brilliance of the voice was undeniable. The same intensity that made the music so compelling also made her career difficult to sustain.

This piece is simply an attempt to think about that paradox: how authenticity and self-destruction can sometimes become intertwined in the lives of great artists.

There are many great singers, but very few voices that feel instantly definitional—voices that seem to arrive already carrying an entire world inside them.

Amy Winehouse was one of those voices.

By the time her second album, Back to Black, exploded in the mid-2000s, it already felt as though she had stepped fully formed out of some earlier musical era. The sound was unmistakably rooted in Motown and 1960s soul, yet the lyrics were brutally modern—messy, confessional, sometimes almost painfully direct.

Winehouse didn’t just sing about heartbreak and addiction. She sang about them as if the audience had wandered into the middle of a private argument she was having with herself.

That tension—between authentic confession and visible self-destruction—became the defining element of her career.

You could hear it most clearly in Rehab, which remains one of the most distinctive pop songs of the twenty-first century. The song is catchy, almost playful on the surface, driven by a swinging brass section that feels lifted from a lost Stax session.

But the lyrics are something else entirely.

They tried to make me go to rehab / I said no, no, no.

It’s funny. It’s defiant. It’s also deeply unsettling, because the listener quickly realizes that the singer is not playing a character. The refusal at the center of the song is real.

In that sense “Rehab” became more than a hit single. It became a kind of thesis statement for the strange artistic space Winehouse occupied. The same vulnerability that gave her music its emotional power also exposed the raw nerves of her life to public view.

You could feel that tension during the years when she was both at the height of her fame and visibly unraveling.

The Glastonbury era captured this perfectly. Winehouse had become a massive international star, yet her stage presence could swing wildly from moment to moment. One minute she would be commanding the crowd with that huge, smoky voice; the next she might appear distracted, fragile, or physically unsteady.

Watching those performances could be oddly uncomfortable. The audience was witnessing genuine brilliance, but it often felt as though the brilliance was emerging from a life that was spinning out of control.

And yet the authenticity of the music was inseparable from that volatility.

Winehouse sang as if every lyric had been torn directly out of lived experience. There was no polite distance between the artist and the material. When she sang about jealousy, addiction, or heartbreak, it sounded less like performance and more like confession.

That quality made her music electrifying. It also made her career precarious.

Pop music has always had a complicated relationship with self-destructive artists. Audiences are drawn to performers who seem emotionally transparent, but the same intensity that produces great art can also be difficult to sustain under the glare of fame.

Winehouse lived inside that contradiction.

The tabloids followed her relentlessly. Every public misstep, every argument, every sign of physical decline became part of a growing media narrative. The spectacle sometimes threatened to overwhelm the music itself.

Yet when she stepped to the microphone and began to sing, the spectacle vanished.

What remained was that extraordinary voice: raw, soulful, and oddly timeless, as if it had traveled forward from another musical generation. In a pop landscape often dominated by carefully engineered personas, Winehouse sounded startlingly real.

That authenticity is why her work still resonates long after her death in 2011.

Many talented singers release successful albums. Only a handful manage to create songs that feel permanently etched into the culture. “Rehab” is one of those songs. The moment those opening horns start, the listener knows exactly what world they are entering.

It is the world of Amy Winehouse: funny, defiant, wounded, brilliant.

A place where honesty and self-destruction were never quite separable—and where the truth of the music was powerful enough to survive them both.

Note:

On Comebacks and Failed Comebacks I: Kofi Annan

Note: This piece begins a small series I’m calling “On Comebacks and Failed Comebacks.” Political and public life are full of attempted returns. Leaders lose elections, wars, or moral arguments and then try to reclaim the stage. Most of these efforts fail. The moment has passed, the audience has moved on, and what once felt urgent has dissolved into what might be called moral fatigue. Yet every so often a different pattern appears. Occasionally someone loses the immediate battle but remains present long enough for history itself to shift. When that happens, what first looked like defeat begins to resemble something closer to a delayed victory. Kofi Annan provides a particularly interesting case. His opposition to the Iraq War did not stop the invasion, and at the time it appeared that the argument had been decisively lost. Yet as the years passed and the consequences of the war became clearer, the moral judgment he articulated gained increasing weight.
In that sense, the story of Annan’s career suggests a useful distinction: some comebacks succeed not because the player reclaims the moment, but because the argument itself eventually catches up with history. Future pieces in this series will look at other figures—some who managed remarkable returns, and others whose comebacks never quite arrived.

Political life especially produces them in abundance. A leader loses a battle—an election, a war, a moral argument—and disappears into the quiet margins where yesterday’s figures slowly fade. The public moves on. The moral urgency of the moment dissolves into what might be called moral fatigue. Outrage that once seemed unstoppable becomes background noise. A new crisis appears, and the world’s attention shifts.

Once this fatigue sets in, comebacks are difficult. The audience that once cared has already drifted elsewhere. The stage has changed. Most players who attempt to return find that the moment that once belonged to them has passed.

Yet every so often a different pattern appears.

Occasionally a figure loses the immediate battle but remains present long enough for the moral tide itself to turn. When that happens, what looked like defeat begins to resemble something else entirely.

Kofi Annan offers one of the most intriguing examples of this phenomenon.

In 2003 the United States and the United Kingdom invaded Iraq. The invasion was justified by a mixture of strategic arguments, intelligence claims, and moral rhetoric about tyranny and liberation. In Washington and London the momentum of the moment was overwhelming. The war was framed as both necessary and inevitable.

The United Nations, by contrast, found itself sidelined. Annan, then serving as Secretary-General, watched as the institution he led was bypassed by the coalition preparing for war. The moment belonged to the advocates of intervention—particularly the group of American policy thinkers who had spent years arguing for the removal of Saddam Hussein.

At the time, it was not at all clear who would ultimately win the argument. What was clear was that the United Nations had lost the immediate struggle for influence. The invasion proceeded without explicit UN authorization, and the diplomatic machinery that Annan represented appeared powerless to prevent it.

The moral emergency that had animated the debate quickly hardened into geopolitical reality.

Then, in September 2004, Annan said something remarkable. In a BBC interview he stated plainly that the invasion of Iraq was illegal under international law.

It was an extraordinary declaration. Rarely does a sitting Secretary-General of the United Nations describe the actions of the world’s most powerful government in such blunt terms. Yet the statement did not produce the dramatic reversal one might imagine. The war continued. Washington and London dismissed the criticism. The machinery of global politics moved forward largely unchanged.

In the short term, Annan had lost the battle.

And the personal toll of that moment appears to have been considerable. In his biography there is a striking image from this period: Annan alone in his darkened living room, unable for a time to rise from the floor. The room itself reportedly kept in near darkness. It was not exactly depression, at least not in the clinical sense, but something close to exhaustion after a prolonged moral struggle that had failed to alter events.

It is a haunting scene. One of the most powerful diplomats in the world sitting on the floor of a dark room, confronting the limits of his influence.

At that moment, the story of Kofi Annan could easily have ended as the story of a failed comeback. A leader who tried to reassert the moral authority of international law and found that the world had already moved on.

But history has a way of rearranging the meaning of certain moments.

As the years passed, the Iraq War came to be widely regarded as a profound strategic and humanitarian mistake. The claims that had justified the invasion collapsed. The war itself destabilized the region and reshaped global politics in ways that few of its original advocates had anticipated.

Gradually, the moral argument that Annan had made—quietly but firmly—became the prevailing historical judgment.

After leaving the United Nations, Annan did not retreat entirely from public life. Instead he reappeared in a different role as a member of The Elders, a group of former statesmen attempting to exert moral influence outside formal political structures.

It was a curious transformation. No longer the head of the UN, Annan had less formal power than he once possessed. Yet his voice now carried a different kind of authority—the authority of someone who had remained in the arena long enough for events to vindicate his judgment.

By the end of his life, the moral verdict on the Iraq War had shifted decisively. Few serious observers still defended the intervention with the confidence that characterized the early years of the conflict. The consensus had moved, slowly but unmistakably, toward the position Annan had articulated when it mattered least.

In this sense, his career offers an unusual example in the history of comebacks.

He lost the battle.
But he may have won the argument.

That distinction matters.

Most political figures attempt comebacks by trying to reclaim the exact moment they once dominated. They want the same stage, the same audience, the same authority. When the moment has passed, the comeback fails.

Annan’s story suggests a different possibility. Sometimes the moral argument itself continues moving through history long after the political battle appears settled. If a leader remains present long enough, the tide may eventually turn.

Which leads to a simple but revealing observation about great players in any arena.

A truly great player is never entirely out of the game.

The moment may pass. The audience may drift away. But if the underlying argument proves sound, history itself has a way of reopening the field.

And when it does, the comeback is already underway.