Posted on by Matt Thomas

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.

Posted on by Matt Thomas

WAYFARER: A PLAY

Note: This piece is a five-act play based loosely on a week I spent in Oxford in 2018. Unlike my previous narrative essays on the same material, (here, here, and here), this is written as a staged work, with dialogue, silence, and structure doing the heavy lifting. At its core, the play explores the tension between experience and narration—what happens when a person tries to turn a living moment into a story too quickly, and what is gained (and lost) in that process. While grounded in real events, it is not strictly autobiographical; it is a shaped and curated version of those experiences. As with all my work, the hope is that it resonates beyond its immediate context. Thank you for reading.

A Five-Act Play

EPIGRAPH

I can’t believe all the good things that you do for me
Sat back in a chair
Like a princess from a faraway place
Nobody’s nice
When you’re older your heart turns to ice

Mark Kozelek — Have You Forgotten

ACT I — THE WAYFARER

Scene 1 — Registration Desk (Threshold)

Lights: institutional white. Gradual warm shift beneath it, as if memory is already leaking into the space.

Sound: distant conference murmur. A faint, unresolved piano note.

A desk. A GATEKEEPER. A lanyard laid out like an object of passage.

MATT enters. Slightly lost. He has clearly been walking longer than intended.

GATEKEEPER
Name?

MATT hesitates. Reaches for something that is not yet ready.

MATT
Here. I think.

He presents credentials.

Stamp sound. Too loud for the space.

The badge is handed back.

CHORUS (from off, soft, not fully placed in space)
Arrival.
Conference.
Inn.
Story begins again.

NARRATOR-MATT (aside, not heard by others)
I thought I came to learn.

The badge feels heavier than it should.

Lights soften.

Scene 2 — Inn Common Room

Warm, slightly unreal hospitality lighting.

Tables. Cups. A space that feels both public and private but refuses to decide which.

ELODIE is present as if she has always been there.

MATT notices her immediately.

NARRATOR-MATT
Voltage.

ELODIE
Tea?

MATT
Yes. Thank you.

Beat. Nothing rushed.

CHORUS (slightly brighter, almost encouraging)
House lady.
Innkeeper.
Muse—

(a correction, quieter)
No. Person.

ELODIE does not acknowledge the Chorus.

Scene 3 — “Sing for Your Supper”

Sound: faint guitar motif. The room subtly shifts into performance space without fully becoming one.

CHORUS subtly rearranges space like memory editing.

MATT sings quietly:

MATT (singing fragment — The Clientele, “The Violet Hour”)
so that summer came and went
and I became cold
yeah I became cold

ELODIE listens. No visible transformation.

NARRATOR-MATT
Hospitality is not destiny.

The room remains unchanged.

Blackout.

ACT II — THE HOT ZONE

Scene 1 — The Casino

Green felt lighting. Rotating overhead spot.

CROUPIER replaces Gatekeeper.

CROUPIER
Place your bet.

MATT
Meaning.

CHORUS
Luck.
Chance.
Myth begins when odds are misread.

MATT places chip.

Sound: chip hits felt—final, sharp.

Scene 2 — Triptych (Three Trips)

Lighting pulses three times. Distinct beats.

MATT (low, repeating)
Three trips.
No more trips.

CHORUS fractures into three figures: GENIE / GHOST / MESSENGER.

NARRATOR-MATT
Inspiration gone.

GENIE (brief, playful)
First.

GHOST (slow, distant)
Memory.

MESSENGER (clear, neutral)
Transmission.

All fade.

Scene 3 — Jungle Confrontation

Green light. Reduced set. No realism.

MATT
Her.
Leave everything.
Frontman.
Practice.

ELODIE
No.

MATT
What is this?

ELODIE
Not your exorcism.

CHORUS
Brink.

Blackout.

ACT III — NAMING THE PATTERN

Scene 1 — Needy Boys

Two chairs. Neutral white light.

ELODIE
Don’t narrate me.

MATT pauses. This lands fully.

NARRATOR-MATT
I was writing her.

Silence.

Scene 2 — Chapel

Stillness. Breath-level sound only.

CHORUS (barely present)
Meaning.
Destiny.
Story.

NARRATOR-MATT
Room, not revelation.

Silence holds.

Scene 3 — Pattern Recognition

Lighting: subtle timeline shifts—memory flickers, not time travel.

NARRATOR-MATT
Senior year.
Again.

ELODIE
Your pattern is yours.

MATT
I see it.

CHORUS
First choice.

Blackout.

ACT IV — RELEASE

Scene 1 — The Offer

Dusk light.

MATT
Part-time.
Scout.
Not jungle.

ELODIE
Boundaries are kindness.

Scene 2 — The Pivot

Warm domestic light replaces earlier symbolic tones.

MATT
Family.
Music.
Life.

CHORUS
Myth.
Escape.
Hero.

MATT
No.

Silence holds. No response from Chorus.

Scene 3 — Chorus Dissolves

Lighting: references dim one by one.

CHORUS removes masks.

NARRATOR-MATT
The story stayed.
The spell lifted.

Blackout.

ACT V — OXFORD CODE

Scene 1 — Gesture

Morning Oxford grey. Minimal space.

ELODIE
Take care.

MATT
You too.

Beat.

No escalation. No closure ritual.

Scene 2 — Benediction (Chapel Revisited)

Same chapel. Quieter now.

Sound: Arvo Pärt piano. Sparse. Non-declarative.

NARRATOR-MATT
Gratitude.

Silence. Breath.

MATT listens without narrating.

Scene 3 — Train

Sound: distant platform announcement. Train readiness.

Gatekeeper becomes CONDUCTOR.

CONDUCTOR
All aboard.

CHORUS
Run back.
Declare.
Confess.

MATT
No.

MATT boards train.

NARRATOR-MATT
The jungle is real.
The girl is real.
The story remains.

Beat.

NARRATOR-MATT (softer)
You think you’ve finished it. Then it comes back different.

NARRATOR-MATT (aside)
She knew more than I could say.

Train departs.

Lights fade with motion, not blackout.

FIN

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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.

Posted on by Matt Thomas

Levels of Lucidity in Dreams: A Close Reading

Illustrations presented with thanks by Riko Kusahara

Note: This piece was written for the Psiber Dreaming Conference offered by IASD in September 2018, under a strict word limit that forced a level of compression I don’t always allow myself. It draws on a series of lucid dreaming experiences to explore how we determine whether we are dreaming or awake, and why those determinations so often fail under pressure. Looking back, I’m less interested in the specific techniques of lucidity than in the broader question the paper circles: what happens when our usual markers of reality—stability, plausibility, even self-awareness—prove unreliable? The result is less a theory of dreaming than a compact record of trying to think clearly inside a system that continually revises its own ground.

Epigraph I:

The difference between most people and myself is that for me the “dividing walls” are transparent.  That is my peculiarity.

—Carl Jung

Epigraph II:

The conventional scientific sentiment has become that—while we don’t totally understand why dreaming happens—the dreams themselves are meaningless. They’re images and sounds we unconsciously collect, almost at random {…} Which seems like a potentially massive misjudgement.

—Chuck Klosterman

Dream I: I awake in a warehouse.  The bed is against one wall–on the other is a thirty-foot mountain of cantaloupes.  I realize I am dreaming.  I get up and run my hands over the cantaloupes.  They feel absolutely real—as tangible as in life.  I remember that tangibility is not a viable reality test—I’ve made that mistake before.  Now fully lucid, I decide to levitate.  The room dissolves, and I float suspended somewhere in dense, colourless space.  Eventually, I feel the need to come back to earth but cannot locate it.  I feel something beneath me.  This is my bed, and I awake back in the warehouse, relieved yet exhilarated.  The cantaloupes are still there, however I don’t question them.  I just happen to live in a room full of fruit.  Moments later I awake again, this time in diurnal “reality.”

The most common dream experience is of waking from a dream we take to be real, only to understand that it was “just a dream.”  However, a subset of dreamers, probably more than we generally imagine, have experienced lucid dreams, dreams in which, to some degree, they are aware they are dreaming.  Lucid dreamers may also experience “false awakenings”[1]— the sensation of waking progressively through dream “levels.”  False awakenings can be disorienting (Robert Waggoner writes that after seven successive false awakenings he “would accept {…} any reality {…} as long as it stayed put”[2]), or sought after (Daniel Love and Keith Hearne have independently developed techniques to induce false awakenings[3]).  Regardless of the desirability of the experience, the existence of dream levels, far from a simple oddity, provides a potential window into massive metaphysical questions.   

First, we need to understand how dreamers use evidence to establish whether they are dreaming or awake.  

II: I am in a dreaming contest with another dreamer.  The contest begins and slimy amphibians begin to appear.  Some resemble frogs; others are in shapes that don’t exist in nature.  Their size varies from that of a pinky to that of a fist and they are very colourful.  I am not trying to dream them, rather they are spilling everywhere around my feet.  I sense this is a dream and check on the other dreamer.  He is standing to my right in empty space.  He looks just like me and hasn’t begun his dream. 

This dream is non-lucid at first and becomes lucid because of the bright color and absurd number of the amphibians.  An awareness beyond the dream senses a non-natural situation.  

III: I am picking out fruit at a fruit stand.  There are some huge avocados, almost too good looking.  I wonder if I am in a dream, and touch an avocado to check.  The one I choose is ripe and soft—I squeeze it a little.  There is no doubt that I am having a tactile experience, and I conclude I am not dreaming.  Of course, I am. 

Two dreams, two types of evidence.  In Dream II, I correctly identify the amphibians as anomalous, and become lucid.  In Dream III, my attempt to test the lifelikeness of the avocado as an indicator fails.  Simply put, realistic sensation is not sufficiently indicative of reality.  Love agrees: “we are not looking for a qualitative difference in how realistic the experience feels {…} we are {…} on the lookout for issues with stability and plausibility.”[4]  In Dream I, at first the huge pile of melons in my bedroom appears implausible and triggers lucidity; after moving up a dream level, my mind overrides the implausibility by “justifying”[5] the anomaly.  

Because we awake from sleep and dreams every morning, we are very familiar with the experience of awakening.  It is therefore unsurprising that when we wake inside a dream we accept the new reality as the waking world, even if it contains anomalous elements.  

IV: I am in a huge house where a large group of families on motorcycles arrive.  The families are making noise all night.  I realize I am dreaming and levitate over to the families.  Later I decide to wake up.  I ease myself out of bed, bumping my nose into an ironing board.  The room looks and feels exactly like my room.  I don’t recall the ironing board being there, but whatever.  Moments later I awake again—the situation is identical, only, the ironing board is gone.  I feel a pit in my stomach, wondering what is ultimately real.

Dream IV is a good example of how dream levels can become increasingly realistic as we move through them.  An ironing board in front of the bed is (for me) more plausible than a house full of bikers.  Dreams such as this beg the question of how we can ever be sure we are awake.  I have dreamt of getting up, walking to the front door, opening it, and emerging into the sunshine in my neighbourhood.  At every point, this dream felt entirely realistic with no anomalies.  After experiences like this, is it wholly unrealistic that we could dream an entire morning?  An entire day?

There are different ways to approach this kind of question.  The first is to use rigorous reality tests.[6]  Using reality tests after each fresh awakening can help us filter anomalies in what may be an increasingly realistic dream state. The second is to open ourselves to a wider set of questions.  Although space limitations make full exploration of these questions impossible, modern dreamers would do well to recall that throughout recorded history people have speculated on the meaning of the dream state and what it can tell us about space, time, life after death, and the nature of reality. 

As dreamers, we know that dreamtime behaves very differently than waking time.  Robert Moss distinguishes between Chronos (“linear time”) and Kairos (the “spacious now.”)  He writes that when Kairos operates in waking life, “ordinary time is {…} suspended or elastic,” and that the world can “quiver or shimmer.”[7]  Moss’ Kairos time sounds a great deal like dreamtime.  Jung in his memoir writes “our concepts of space and time have only approximate validity,”[8]  and “there are indications that at least a part of the psyche is not subject to the laws of space and time.”[9]  Jung makes multiple connections between dreams and life after death, suggesting that our waking world,

in which we are “conscious,” may in fact be a projection of a more “real” and permanent, even timeless, unconscious.[10] 

In the Tibetan tradition of dream yoga, the yogi prepares for death through dreams and meditation, entering death consciously by releasing the bodily energy in such a way that the body partially or entirely dissolves into pure light.  This “rainbow body” is well-documented in Tibet and China, and cases of this phenomenon have been reported across multiple religious traditions.[11]  Finally, Moss connects dreams with the much discussed Many Worlds theory, as does, in popular culture, Richard Linklater. [12]

V:  I am among a large group of people on the top floor of a building.  We lie down on our backs and form bundles.  The molecular structure of these bundles begins to dissolve, we become lighter, then totally empty.  This process is dictated by a power outside of us which doesn’t speak.  Once empty, we have the choice to become anything we want.  I choose to become white light.  Suddenly I am transported through space in a burst of pure white light, my old body left entirely behind.  This is the most peaceful and thrilling feeling in the world.  Then, I am back into a new bundle, trying again to become empty.  I make progress, but it is hard and I am over-concentrating.  Progress ceases; I wake up. 

Although I have thought at length about dreams, I am a normal person with a normal job, dreaming anonymously night after night.  I don’t belong to a spiritual tradition, am not a yogi or a meditating hermit.  As a lucid dreamer, like many of us, I am self-taught.  While we anonymous dreamers are wise to suspend judgement about the particularities of a theory as mind-boggling as dreams as an interface to infinite parallel universes, it is perhaps not by chance that my dreams of ascending to a state of pure white light bear close resemblance to innumerable near-death experiences or the reported manifestations of a lifetime of dream yoga.  Although admittedly outside of our normal rational mode of apprehension, the experience of journeying through multiple dream levels, and the energy and amazement which often accompany these experiences, may point the way toward worlds far above, below, or beyond our own.  

Who are we in our trek through life?  Are we the maker, or the made?  The writer, or the page?  The actor, or the stage?  The happening, or the happened to?  Perhaps, our ability to exercise agency in the vastness of forever depends in part on learning to navigate levels of “reality,” however we encounter them.  Or, perhaps, journeying to the far side of the dream can bring us face to face with that which is actually dreaming us.

Bibliography

Jung, Carl. Memories, Dreams, Reflections. Vintage Books, 1989.

Linklater, Richard, director. Slacker. Orion Classics, 1990.

Love, Daniel. Are you Dreaming? Enchanted Loom Publishing, 2013.

Moss, Robert. Sidewalk Oracles. New World Library, 2015.

Rinpoche, Gyalwai Nyugu.  “About Rainbow Body.” http://www.gyalwai-nyugu.com/about-rainbow-body/.  Accessed 24 July 2018.

Rinpoche, Tenzin Wangyal. The Tibetan Yogas of Dream and Sleep. Snow Lion Publications, 1998.

Thomas, Matthew.  “On Coming Through”: A New Meditation on Intention. https://craftfollowsconcept.com/2013/05/13/on-coming-through-statement-of-intent-on-the-approach-of-my-39th-birthday/#more-11. Accessed 24 July 2018.

Waggoner, Robert. Lucid Dreaming. Moment Point Press, 2009.

[1] Waggoner, 61

[2] ibid., 63

[3] Love, 131

[4] Love, 71

[5] Love cites “poor reasoning skills” as one common reason for failing to recognize dream signs and achieve lucidity.  Love, 73.

[6] Love, 78-79; Waggoner, 259.  (Wagonner uses the term “reality check” instead of “reality test.”)

[7] Moss, 49

[8] Jung, 300

[9] ibid., 304

[10] ibid., 324

[11] Tenzin Wangyal Rinpoche, 314; Gyalwai Nyugu Rinpoche

[12] Moss, 74-74; Linklater

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On the Pre-Game (aka A Response to Neil Strauss’ The Game)

Note: This piece overlaps my three essays on my week with Isobel series (I–III), though it approaches that week from a different direction. Where those pieces follow the arc, this one lingers on the moment before it resolves—the pre-game, as I’ve come to understand it. It is also a direct response to the book The Game, by Neil Strauss. In what follows I don’t intend to rebut Strauss so much as correct what I see as a fundamental weakness in the subculture he dissects. The reader will judge whether I succeed.

Epigraph

“No one else could play that tune, you know it was up to me.”

— Bob Dylan, Up to Me

Part I: Ippei

I’m at Zaza, the club on Kiyamachi in Kyoto. It’s around 11 PM and just getting going. Zaza is a late night place. It doesn’t peak until well past midnight, and at this hour it’s still stretching, still finding its rhythm.

I’m there by myself, drinking a White Russian.

A Japanese guy comes up to me. He’s about fifty-five. No preamble, no easing into it. He introduces himself—let’s call him Ippei—and within seconds it’s on.

“See those two ladies over by the window,” he says. “Wanna help me pick them up?”

I’m intrigued. Not because I’m especially interested in the outcome, but because I’m a curious guy and I want to see what he’s doing.

“Ok,” I say. “What’s the play?”

He doesn’t hesitate.

“You’re my old friend from California. I haven’t seen you in twenty years. I just ran into you by chance here. Take it from there.”

That’s it. That’s the entire setup. Handed to me fully formed.

I ask him, just to check, “Is this going to work?”

He smiles, completely unbothered.

“Yeah,” he says. “I do this every night. Had a threesome last night.”

Well alright then.

We walk over. He starts talking immediately, in Japanese, smooth, fast, confident. “This is Matt, my best friend from California. Would you believe I just found him here?”

I met him five minutes ago.

It doesn’t matter.

In no time the two women are completely engaged. Smiling, leaning in, laughing. The story has landed. The reality has been accepted. They’re not being approached. They’ve been included.

And I’m there, but I’m not really there. I’m not trying to win anything. I’m not trying to escalate. I’m watching. Taking it in. The nightlife anthropologist, just observing the field.

After a while I step out to the balcony to smoke.

Twenty minutes pass.

When I come back down, he’s still there. Still going strong. Still inside the same story.

That’s when it clicks.

He didn’t need me.

He needed the role I filled.

He needed a premise.

Part II: Neil Strauss

Neil Strauss’ The game

That night at Zaza stuck with me, not because of what happened, but because of what it revealed.

There is a whole body of writing—call it a subculture, call it a system—that attempts to explain and formalize moments like that. The most famous version of it is The Game, by Neil Strauss, which I’ve read twice.

I want to be clear about something before I go any further.

I’m not anti–Neil Strauss. In fact, I respect him. He’s an elite investigator of subcultures, and I love subcultures. He embedded himself in a world, learned its language, mapped its hierarchies, and reported it out with real precision. That’s not easy to do. It’s a serious piece of work.

What follows is not a dismissal of Strauss.

It’s a response to what the game represents.

Because once you move from observing a system to adopting it, something changes.

At its core, the game assumes that attraction can be engineered. That with the right language, the right sequence, the right calibrated signals, you can break down a woman’s resistance and get to the desired outcome, which is of course bed.

It’s a kind of a linguistic technology and NLP at its worst. A system designed to move someone from one state to another.

And for me, that’s where I part ways.

For me The Game is a massive turnoff, because it flattens everything and kills any chance at romance.

It scripts what should be alive. It reduces seduction to a manual and turns something unpredictable into something repeatable. And in doing so, it drains it of the very thing that makes it worth pursuing in the first place.

There’s no space for real connection. No space for the unexpected. No space for the moment where something happens that neither person could have predicted. No space for the kind of encounter that might actually change your life.

And beyond that, it produces a life that I don’t want.

The guys in The Game end up living together in this kind of shared house—Mystery, Strauss, Courtney Love—surrounded by other guys, talking about women, thinking about women, analyzing women. It’s a sausage fest. And it’s not cool.

The Gamers think they’re players. I prefer to think of them as incel-adjacent. They’ve optimized the system, but they’ve lost the thing itself. They’ve mastered the game and stepped outside of life.

Part III: On Action

I’ve had a handful of sexual partners that I’ve gone all the way with. The precise number is under an NDA. I’ve made out with more. But I haven’t been especially active, at least not in the way the game would define it.

What I have done is, flirt with, connect with, and have crushes on dozens of women.

And the truth is, I enjoy it.

I actively enjoy the pre-game.

I enjoy getting close. The moment before something becomes something else. The tension. The ambiguity. The recognition that something might be there, and neither of you has named it yet.

The thrill of newness and the possibility of a spark. If it burns, great. If it flickers, that’s also good. For most men, the pre-game is a means to an end. For me, it’s the end.

And that’s the difference.

This doesn’t mean I’m not interested in action. I am. Very much so. In fact, I’m something of an action junkie. But I’m a highly specific kind of action junkie. Like Wittgenstein, who was said to have manufactured his own oxygen, I manufacture my own action.

I don’t chase it blindly. I don’t optimize for it. I don’t try to force it into existence through systems or scripts. I generate it. Selectively. Intentionally. And in moments where it actually means something.

Part III: Luna

I’m at Umineko with a friend—call him Mr. Editor. It’s early, maybe six in the evening. We’re mid-bar, having a beer, when I notice a woman sitting off to the side.

She’s stunning. And I HAVE to go talk to her. Not because I expect anything to happen. Not because I’ve calculated the odds. But because the moment demands it.

I tell Mr. Editor what I’m about to do. He nods. “Go for it,” he says. “I’ll watch.” I walk over and ask her name. She smiles. “Call me Luna.”

We speak in Japanese. The conversation flows. I bring everything I have to the moment—attention, presence, curiosity—and it lands. There’s a spark. Not forced. Not engineered. Just there.

We talk for a while. Long enough for the room to shift slightly around us. Eventually I ask for her Instagram. She gives it to me. I walk back to the bar and sit down next to Mr. Editor. I’m on Cloud 9. The next day, in the late afternoon, carefully timed, I send her a message but she doesn’t reply.

Failure? Not for the pre-gamer. Because the pre-gamer already got what he came for. The moment. The spark. The approach. The brief, electric possibility that something might happen. That was the action. That was the point. For the Strauss guys, the night ends when the text goes unanswered. For me, the night ended at the bar.

Up to this point, the pre-game is contained. Safe, even. A space where things can happen or not happen without consequence.

But sometimes it doesn’t stay that way.

Isobel Revisited:

I have written about my week with Isobel extensively elsewhere, however part of that story is relevant to what we are discussing here. I met her at the Faculty of Astrological Studies, held at Exter College, Oxford, in late August 2018. We spent the week together and I fell in love. But I didn’t sleep with her. My choice. What follows is a light re-write from my essay “On My Week with Isobel: Part II”:

Wednesday.

I wake up early and we have breakfast together in the dining hall. By this point, people are noticing us. Comments here and there, snickers, sideways smiles.

Morning and lunch blur into one long conversation—the garden, the bench, a little grass, nothing hidden. We’re finishing each other’s thoughts. I’m in deeper than I’ve ever been.

We don’t attend much of anything.

In the afternoon break she goes to change. I go back to my room and put on The Mendoza Line with the full weight of obsession. She comes back after and tells me, without shame, that she had pleasured herself during the break. Just fucking states it.

This is a complication.

That night she changes again. A red dress. Short, but not careless. Stunning. We sit at dinner whispering, touching lightly, laughing against each other. Everyone knows by now.

After dinner there’s wine again, talking with the tutors, the long courtyard. I meet Darby Costello in person for the first time. She’s fully alive, drinking wine, holding the room effortlessly. I’m so happy she’s my astrologer. But I’m elsewhere.

We stay late. Clear the courtyard. Around two in the morning we part. Cheeks touched. No bedroom. No act. No close. Back in my room, lights low, Mendoza Line still in my ears, I lie on the narrow bed and I know exactly where I am standing.

I will keep going. I will see where this leads. But I will not sleep with her. I can’t.

It’s not that I don’t want to. I do. Totally and much more. But I can see it. The complications. For her, for me. The chain of events that would follow. I’m old enough to see it coming. And I know, standing there in the courtyard, with the last of the wine and a cigarette burning down, that it’s on me.

I have to be the one to say no. That’s the shape. That’s the decision.

=====

Up to this point, the pre-game has been something I could enter and exit at will. A space I could step into, generate action, feel the spark, and leave intact.

With Ippei, the action was scripted. With Strauss, it was systematized. With Luna, it was self-contained.

But there’s another version of the pre-game, and it’s the one that matters most. The one where the moment doesn’t stay light. The one where it deepens. Where the spark doesn’t just flicker—it starts to take shape. And at that point, something shifts. Because now it’s not just about whether something will happen. It’s about whether it should.

This is where the line from Dylan starts to carry real weight. No one else could play that tune. There’s no system here. No script. No borrowed language. No Ippei handing you a premise. There is only the moment as it actually exists, and your ability to see it clearly.

And then the second part. It was up to me. Not to escalate. Not to optimize. But to decide. The game ends when something happens. The pre-game ends when you decide it should.

Dedication

For pre-gamers everywhere. May you get a little action tonight baby.

Note: If you liked this piece, you may also like the following pieces that also take up the themes of romance and seduction.

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