My Favorite Songs of All Time: 1-20 With Commentary

Music motherfucking rules

Me

I hear the aged footsteps
Like a motion on the sea
Sometimes I turn there’s someone there
Other times it’s only me

Bob Dylan

They say that victory’s sweet
Even deep in the cheap seats

Conor Obrest

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 250 this time in several 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 have hoped for. This list does not include ambient music or jazz, two genres I also love. The 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 here.

1. Cape Canaveral — Conor Oberst

For the first time since I began making versions of this list, I have a new number one. Conor Obrest’s Cape Canaveral has slowly, almost imperceptibly, worked its way past every other song I love. I didn’t exactly wake up one morning and decide that it was the greatest song ever. I simply noticed that I had already begun treating it that way. I return to it constantly, and it still gives me full-body chills and moves me to tears almost every time I hear it. After nearly forty years of obsessive music listening, Cape is as good of a number that I can come up with.

Conor is my number five artist of all time, and the fact that Cape Canaveral has become the song above all others that explains why. Number one. There it is. Man oh man. I didn’t see this one coming.

I have loved Cope for about eight years since I first heard it shorty after the release of the record it is on, Conor’s solo self titled debut from 2008. It is in my opinion his most beautiful and moving song. Conor also wrote my number 13 favorite song, Easy/Lucky/Free, which I write about below. Cape Canaveral uses the space program—those televised launches from decades ago, 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 in which 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.” This is one of the loveliest 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, however it is oddly triumphant. It’s about making meaning over time, with partial access, and moving from watching to 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 three artist of all time, and Cape Canaveral is exactly why.

2. Leaving LA — Father John Misty 

As of recently, “Leaving L.A.” is my second favorite song of all time. I first heard it when Father John Misty released Pure Comedy in 2017, and I can remember almost exactly where I was. I was walking after work, headphones on, going down the stairs at a train station on my way to a Starbucks. I have had exactly two genuine musical epiphanies in my life. The first came in the summer of 1991, when I heard Bob Dylan’s acoustic “Every Grain of Sand”—the famous barking-dog version—on The Bootleg Series Volumes 1–3. The second came walking down those stairs listening to “Leaving L.A.” The song absolutely fucking flooded me.

And it is a motherfucker of a song. Thirteen minutes long, mostly acoustic, essentially one enormous unfolding narrative, and utterly unconcerned with whether you have the patience to follow it. Misty moves through his accelerating fame and his profound ambivalence about the same; Los Angeles and the absurdity of being a successful singer-songwriter there; marriage; self-mythology; artistic pretension; mortality; and his own suspicion that perhaps writing a thirteen-minute acoustic song about all of this is itself ridiculous. He even takes a drive-by at Amy Grant and contemporary Christian music along the way. Nobody is safe, least of all Father John Misty.

One of the song’s funniest passages is his description of music that sounds like “dollar signs and Amy Grant,” part of a larger assault on commercially manufactured profundity. But the jokes never exist merely as jokes. Misty keeps using comedy to approach things he cannot quite approach straight on. The strangest and best example is his childhood story about nearly choking to death on watermelon candy while shopping with his mother. An apparently ridiculous memory suddenly opens onto mortality: the adult artist looking backward at the child who could simply have ceased to exist right there, before any of the fame, records, marriage, drinking, jokes, or bullshit ever happened.

That movement—from comic digression into something unexpectedly frightening or tender—is the song’s great trick. “Leaving L.A.” keeps wandering away from its subject only to reveal that the wandering is its subject. This is a song about the stories we construct around ourselves, and about the increasingly absurd position of a man becoming famous for constructing stories about himself while simultaneously distrusting the entire enterprise.

And then the song closes movingly by bringing all that sprawl back down to two people and the possibility of another life: he could quit drinking; she could write her script. Yeah, right. As of this writing, I have no real clue whether Father John Misty has quit drinking, and no idea whether his best girl ever wrote that script. I hope so. What matters inside the song is that for a moment another version of their lives becomes imaginable—less spectacular, perhaps, but also less ridiculous. After thirteen minutes spent exploding his own mythology, Misty ends with something remarkably small and human.

I keep this one beside me at all times. It is one of the handful of songs I love falling asleep to, partly because its length and pace allow me simply to disappear inside it. Sometimes I make it to the end and sometimes I don’t. It hardly matters. I love this song and every line in it.

“Leaving L.A.” is the towering centerpiece of Pure Comedy, and it is by some distance my favorite Father John Misty song. There are plenty of others I greatly enjoy—“I’m Writing a Novel,” “The Night Josh Tillman Came to Our Apt.,” “Hollywood Forever Cemetery Sings,” “Chateau Lobby #4 (in C for Two Virgins),” “Mr. Tillman,” and “Nancy From Now On” among them—but none has ever hit me remotely like this one.

Thirteen-minute acoustic songs are not generally how one goes about acquiring casual listeners. Fine. If you are a literate music fan with any tolerance at all for the long, digressive, dirge-like form, give it thirteen minutes and let the bastard work on you. It has been working on me since the first time I heard it walking down those train-station stairs.

Number two. Father John Misty fucking rules.

3. Cruiser — Red House Painters

“Cruiser” is my third favorite song of all time. It narrowly nudges out Whiskeytown’s glorious “Houses on the Hill” and Craig Finn’s absolutely amazing “It’s Never Been a Fair Fight.” Right now I have it placed just behind “Leaving L.A.,” but damn, is it close. Full-body goosebumps. Tears. The whole fucking thing.

Like “Leaving L.A.,” “Cruiser” is a long song, and it has absolutely no interest in hurrying. It seems to be about the singer’s love for, or fascination with, a Japanese woman living in Los Angeles. According to the song, she possesses the “biggest smile from Tokyo,” and she came out to Los Angeles five years earlier. So there we are: Kozelek, a recent Japanese transplant, Los Angeles, and a car. That is more than enough to build a world.

The song meanders and takes its time. Along the way we get a tour of Los Angeles as it existed when Kozelek wrote it: driving around, streets and neighborhoods passing by, the city experienced not as a collection of landmarks but from inside a moving car. That matters. “Cruiser” really does cruise. It has the strange floating quality of driving around a city with nowhere particularly urgent to be, when the person beside you and whatever is coming through the speakers become more important than the destination.

And naturally, music is part of the landscape. One of the things I have always loved about artists like Kozelek is that beneath all the songwriting, mythology, and accumulated weirdness, they remain genuine music fans. Kozelek has spent his entire career listening, absorbing, interpreting, and arguing with other people’s songs. He has covered AC/DC, Modest Mouse, John Denver, Kris Kristofferson, Paul McCartney, and many others, often transforming the source material so completely that the cover becomes a Kozelek song.

I especially love his version of AC/DC’s “Rock ’n’ Roll Singer.” The original is a little too goofy for me; Kozelek strips away the attempted humor and plays the thing completely straight. Under the Red House Painters name, he recorded an acoustic version, and later, under his Sun Kil Moon moniker, he returned to it electrically. Suddenly what had been a cocky young rock song becomes something closer to a statement of purpose: this is what I wanted to become, and this is what I became. His cover of Modest Mouse’s “Never Ending Math Equation” is similarly amazing. Kozelek is an incredible singer, but he is also an extraordinary interpreter of the rock-and-roll canon.

And that musical consciousness matters in “Cruiser,” because the song feels partly like Kozelek constructing his own little canon in real time: the woman, the car, Los Angeles, whatever is playing, memory already forming while the experience itself is still happening. The city becomes inseparable from the music, and the music becomes inseparable from the person sitting beside him.

There are many Kozelek songs I love, and several more will appear below. “Have You Forgotten,” “Michigan,” “Japanese to English,” “Rock ’n’ Roll Singer,” and others all have legitimate claims on me. But “Cruiser,” for my money, stands head and shoulders above the rest.

It is romantic without being sentimental, sprawling without becoming shapeless, and beautiful without seeming to work particularly hard at being beautiful. It just rolls along until somehow you realize it has completely fucking destroyed you.

Number three. My man.

4 (t). Houses on the Hill

“Houses on the Hill” appears on Whiskeytown’s 1997 masterpiece Strangers Almanac. Until about a month ago, I was convinced that Strangers Almanac was by far Whiskeytown’s best record. Their final album, Pneumonia, is great too, of course, and contains “Jacksonville Skyline” as well as the absolutely glorious and unbelievably beautiful ballad “My Hometown.” But recently I’ve been getting deep into their 1995 debut, Faithless Street, and today I consider it every bit as good as Strangers Almanac. Songs such as the title track, “Lo-Fi Tennessee Mountain Angel,” and “Mining Town” stand out, along with many others.

However, it is “Houses on the Hill” that remains my very favorite Whiskeytown song.

The lyric is simply wonderful. The song reaches backward into another generation and constructs an entire vanished life out of photographs, letters, houses, war, and memory. My favorite moment comes when the narrator describes a young man being sent off to World War II. He leaves behind the woman he loves and carries her picture with him when he goes ashore. That tiny sequence absolutely destroys me. Ryan Adams can toss off an image like that almost casually and suddenly an entire life—love, separation, war, mortality—is sitting there inside a couple of lines.

Motherfucking full-body goosebumps. Full-body tears.

A lot of songs make me cry, and “Houses on the Hill” is right near the top of the list. Part of its power is how little it insists upon itself. There is no giant emotional announcement. Adams and Caitlin Cary, who co-wrote the song, simply let these remnants of somebody else’s life accumulate until the emotional weight becomes almost unbearable. It is a song about what survives people: houses, photographs, letters, stories—and the people who come afterward trying to reconstruct what those objects once meant.

I especially love the live-in-the-studio version included with the deluxe Strangers Almanac. The studio version is great. I love the studio versions of virtually all my favorite songs, obviously. But for whatever reason, I tend to love live versions even more, and this one is no exception. The performance was recorded for KCRW in September 1997, and it opens the song up beautifully; even the instrumental ending seems to let some additional air into the story. 

Ryan Adams has gone on to have an almost absurdly prolific career. His official discography already runs to dozens of releases, beginning with his solo debut Heartbreaker in 2000 and continuing right through new music in 2026. Heartbreaker contains “Oh My Sweet Carolina,” another of my favorite Adams songs and one that appears later in this list. There are many, many others.

But for now, “Houses on the Hill” remains my favorite Whiskeytown/Ryan Adams song by a little ways.

It simply fucking rules. Stay tuned.

4 (t). It’s Never Been a Fair Fight

5. Tulsa Queen — Emmylou Harris.

For years, “Tulsa Queen” was my answer to the question “what is the greatest song ever.” It was number one I thought. Don’t bother asking me again. And then, eventually, Cape Canaveral by Conor Obrest slipped past it. Barely. This isn’t really a demotion so much as the smallest possible movement inside the topmost tier: Tulsa Queen remains one of the most overwhelming pieces of music I have ever heard, and Emmylou Harris remains, for my money, the greatest vocalist who ever lived.

Then straight into:

I get full body chills and my eyes well up with tears every time I hear it…

The existing conclusion needs the corresponding tiny adjustment. Instead of “The GOAT. Pure legend. Full stop,” which contradicts #2, I’d go:

For a very long time, Tulsa Queen was the GOAT. Now it is number five. Nothing about the song has changed. I did. It is still absolutely legendary. Always will be.

I get full body chills and my eyes well up with tears every time I hear Tulsa Queen. Emmylou is the greatest vocalist of all time by far, and Tulsa presents the clearest 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. The song starts—“I saw the train/ in the Tulsa night/ calling out my name/ looking for a fight”—and it’s just pure magic. Just unbelievable. 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 and 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. Emmylou baby you remain the GOAT.

6. Faded — Afghan Whigs.

The Afghan Whigs’ lead singer Greg Dulli does something remarkable of Faded, 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 seven.

7. 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 ManOne 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.

8 (T). Never Aim to Please — Bash and Pop

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 nine.

9. A Bathtub in the Kitchen — Craig Finn.

My favorite of many possible Finn contendersBathtub 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 nine.

10. Dreadful — The Violet Burning

“Dreadful” by The Violet Burning fucking slaps. That’s really all there is to it. It just slaps. So damn hard.

The song is only two minutes and twenty-eight seconds long, and it is just totally dialed in. There’s no wasted motion, no long setup, no attempt to turn itself into something grander than it needs to be. It comes in, kicks ass, and gets out. I spend a lot of time in hotels and if “Dreadful” is playing when I leave the room, I usually leave it playing as loud as I can for, as I like to say, my good angels. Angels rule. Why not?

The Violet Burning are a criminally underrated band. Basically nobody today knows who they are, but I do, and I have loved them for years. The band began around 1990 in Orange County, California, and from the beginning the central figure has been singer, guitarist, and songwriter Michael Pritzl. The musicians around him have changed repeatedly over the decades, but Pritzl has remained the constant—the voice, songwriter, guitarist, and creative mainspring of the whole enterprise. 

And what an enterprise it has been. Pritzl has made more than twenty albums, EPs, and live recordings under The Violet Burning and related names, toured relentlessly through the United States and Europe, and somehow maintained a fiercely loyal audience while remaining almost completely outside the mainstream. Their early sound drew from post-punk and alternative rock—The Cure, U2, Echo & the Bunnymen—and over time expanded into the huge, atmospheric guitar music that has over time became unmistakably theirs. 

The Violet Burning came out of the Christian alternative-rock world, although Pritzl has never exactly fit comfortably inside that box. That puts him in the same broad lineage as people like Larry Norman, Gene Eugene, and Michael Knott: artists for whom faith was part of the work but never sufficient to explain the work. The music is too strange, too wounded, too beautiful, and often simply too fucking loud for that. Pritzl himself has always seemed interested in the collision between devotion and doubt, beauty and damage, transcendence and straight-up rock and roll.

R.I.P. Gene Eugene, the man. And R.I.P. Michael Knott, the motherfucking badass of all badasses.

In addition to being hugely underrated, parts of The Violet Burning catalog remain frustratingly difficult to find on the major streaming services. That is a real shame, because this is precisely the sort of band that should be continually rediscovered. They built an enormous body of work without ever becoming remotely as famous as the quality of that work deserved. Even at their commercial peak they were essentially an independent proposition, building their audience through touring and word of mouth rather than anything resembling mainstream success. 

I wish more people knew The Violet Burning. I wish more people heard these songs.

My number two Violet Burning song is “Gorgeous,” which we’ll get to a little later. That song is enormous, emotional, and glorious in an entirely different way. But for now, “Dreadful” is the one.

Two minutes and twenty-eight seconds. Nothing wasted.

Number ten.

This bad boy fucking slaps.

11. 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.

12. Gorgeous (live)— The Violet Burning

“Gorgeous” is gorgeous. It is gorgeous, as indicated by the title, and probably one of the most gorgeous songs ever recorded. This is my number two favorite Violet Burning song, as indicated in my discussion of “Dreadful” above. The Violet Burning is a criminally underrated band. I will never understand how they don’t have a bigger footprint. They deserve to be widely recognized and appreciated.

While Dreadful is almost certainly the slappiest song of all time, if that is a thing, Gorgeous is absolutely one of the sweetest. It starts with Michael Pritzl, the band’s lead singer and creative center, singing, “I swear it was the Fourth of July.” Oh yeah, Michael? Are you sure? Okay, baby, whatever you say. So yeah, it’s the Fourth of July: patriotism, mom and pop, apple pie, fireworks—the whole nine. But Pritzl immediately turns all of that American iconography into the language of romantic awe. The fireworks aren’t really the point. The person he is looking at is.

And then the song eventually delivers its payoff: baby, you’re so gorgeous.

Motherfucker.

Of course.

Gorgeous originally appeared on Demonstrates Plastic and Elastic, released in 2001, one of the strangest and more adventurous records in The Violet Burning catalog. The album moves between glam, alternative rock, electronics, enormous guitars, and quieter atmospheric material, with Gorgeous arriving towards the end. It is a perfect example of what makes Michael Pritzl such an unusual songwriter: underneath all the sonic experimentation is a deeply sincere romantic. He can build a wall of noise around a feeling, but he never seems embarrassed by the feeling itself.

Pritzl has described honesty and vulnerability—including honest conversations about God and ordinary human life—as central to what the band does. He specifically included Gorgeous among the songs on Demonstrates Plastic and Elastic that embody that impulse. That combination—spiritual yearning, romantic yearning, distortion, beauty—is basically the Violet Burning universe in miniature.

And Gorgeous has endured. It remained important enough to the band to appear late in sets and sometimes close them many years after its release. I particularly love the live versions because Pritzl can stretch the song outward until what begins as a simple declaration of attraction becomes something much larger. The sweetness survives the volume. If anything, the volume makes it sweeter.

That is also why I can put Dreadful and Gorgeous this high on the same list without feeling remotely repetitive. They represent opposite poles of what I love about this band. Dreadful fucking slaps. Gorgeous fucking glows. One makes me want to turn the stereo up until the walls shake; the other reminds me that sometimes the most effective thing a songwriter can do is look at another human being and say the simplest possible thing: you are gorgeous.

And Michael Pritzl makes me believe him every goddamn time.

13. Albuquerque Mark Kozelek (Neil Young Cover)

Well, they say that Santa Fe
Is less than ninety miles away
And I got time to roll another number and rent a car
Oh, Albuquerque.

Oh my God, Neil. What are you doing to me? Neil, baby, you’re breaking my heart. Neil, shut the fuck up.

“Albuquerque” appears on the back end of Neil Young’s 1975 record Tonight’s the Night, immediately before “New Mama.” “Roll Another Number (For the Road),” with which I constantly confuse it for reasons that will shortly become obvious, appears a few songs earlier. Tonight’s the Night, as many readers will remember, is Neil’s record most haunted by death. It was largely recorded in 1973 but held back until 1975, and the deaths of Crazy Horse guitarist, singer, and songwriter Danny Whitten and Young’s roadie Bruce Berry hang over the entire thing.

Berry is famously eulogized in the two versions of “Tonight’s the Night” that bookend the record: “Bruce Berry was a working man / He used to load that Econoline van.” Neil, my man.

Obviously Neil Young loved Bruce Berry and Danny Whitten. He basically wrote an entire record out of the grief that followed their deaths. Tonight’s the Night is consequently a strange, ragged, drunken, grief-stricken motherfucker of a record. It sounds at times as though everybody involved is barely holding the thing together, which is exactly why it works.

Tonight’s the Night also includes one of the first Neil Young songs I ever heard, “Tired Eyes,” with the stone-cold classic opening: “Well, he shot four men in a cocaine deal / And he left them lying in an open field / Full of old cars with bullet holes in the mirrors.”

Neil. Bullet holes in the mirrors? Really, baby? Again: oh my.

In any case, I often get “Albuquerque” and “Roll Another Number” confused, simply because “Albuquerque” itself contains the line, “So I’ll roll another number for the road / I feel able to get under any load.” Obviously Mr. Young was rolling his own during this period.

Probably other periods too.

But my favorite lines from “Albuquerque” are these: “So I’ll stop when I can / Find some fried eggs and country ham / I’ll find somewhere where they don’t care who I am.”

Motherfucker.

By 1975, Neil Young was already a global superstar. He was massive in his native Canada, massive in the United States, and increasingly massive around the world. In his wonderful song “Don’t Be Denied,” Young writes about reaching that point—record executives suddenly all over him and the band when all he really wanted to do was play rock and roll. Neil, fucking do it.

And that context is part of what makes “Albuquerque” so moving. This is a famous man singing about wanting to disappear. He doesn’t want the record company, the expectations, the mythology, or apparently anybody asking where the hell Neil Young is. He wants to get into a car, roll another number, eat some fried eggs and country ham, and go somewhere where nobody cares who he is. It is an almost comically modest fantasy of escape, which is precisely why it works.

And then there is Mark Kozelek. I love Neil Young’s original, obviously, but it is Kozelek’s cover that gets the spot on this list. Kozelek has always been a magnificent interpreter of other people’s songs—AC/DC, John Denver, Modest Mouse, Paul McCartney, Kris Kristofferson, and many others—and he understands exactly what makes “Albuquerque” work. He doesn’t try to improve Neil Young. He slows everything down, opens up the spaces between the words, and lets the loneliness that was already buried in the song come completely to the surface.

That is what the best covers do. They don’t replace the original; they reveal something that was already there. Neil Young wrote a great song about escape. Mark Kozelek heard the loneliness inside the escape and made it almost unbearably beautiful.

Fried eggs. Country ham. Nobody caring who you are. Sometimes that is the whole fucking dream.

Neil, my man. My god what an amazing song.

14. 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 ApproximatelyOh My God, Whatever, Etc.Still a CageBirmingham—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 fifteen.

15. (T) Montreal Rock Band Somewhere — Happyness

“Montreal Rock Band Somewhere” is totally out of control. Of course it is. What else can you say about a song that contains the lyric, “I’m wearing Win Butler’s hair / There’s a scalpless singer of a Montreal rock band somewhere”? Win Butler is, of course, the lead singer of Arcade Fire, who suck.

They suck.

Arcade Fire hit the big time with Funeral, released in 2004. I like Funeral okay, but I haven’t listened to it in more than a decade, and I probably never will again. It just isn’t my speed. It sounds to me like a concept record: operatic, overblown, and the production lets it down at every turn.

So yeah, I don’t like Arcade Fire.

However, Happyness is massively underrated. Other than The Violet Burning and maybe Daddy Issues, Happyness is, to my mind, the most underrated band of all time. And that is saying something.

“Montreal Rock Band Somewhere” runs 5:04, and it is a sprawling guitar workout that somehow feels much bigger than its running time. The Happyness boys can really fucking play. That sometimes gets obscured by how funny they are, and by the deliberately tossed-off quality of the whole operation. The songs can sound as though three guys wandered into a room, made each other laugh, picked up their instruments, and accidentally recorded something brilliant. But listen underneath the jokes: these guys know exactly what they are doing.

There is also some weird history surrounding the song’s placement. Weird Little Birthday was originally released in the UK in 2014 as a 13-song record without “Montreal Rock Band Somewhere.” The expanded 2015 release added four bonus songs, with “Montreal” coming immediately after what had originally been the album closer, “Monkey in the City.” That expanded record also contains “Orange Luz” and the wonderfully titled “Refrigerate Her,” but those were already part of the original album. 

I am fascinated by song order on records, and I spend a ridiculous amount of time thinking and writing about it. “Janie Jones” goes first. “Rocks Off” goes first. Some songs simply announce themselves as openers or closers. “Montreal Rock Band Somewhere” feels to me like a closer: sprawling, funny, strange, guitar-heavy, and just unresolved enough to leave the record hanging in the air after it ends.

There are plenty of other great songs on Weird Little Birthday, including the title track and “Leave the Party.” In “Leave the Party,” for example, the narrator proposes killing everyone at the party and then heading home.

Really, baby? You’re going to murder the whole party and just jet like that? Settle down. Take a shower. Think things through. Not the best move perhaps.

They followed the debut with Write In in 2017 and eventually Floatr in 2020, a much slower, denser, stranger record. I like Floatr, but it is not an easy record to get into. The immediacy and wiseass humor of Weird Little Birthday are still there in places, but everything feels more submerged. It is the sort of record that asks you to come toward it rather than coming toward you.

And maybe that helps explain why Happyness never really broke through. They were always slightly sideways to whatever might have made them commercially successful. They can write hooks, they can make enormous guitar noise, the songs are genuinely beautiful, and they are extremely funny. However for some reason they never seemed particularly interested in making things easy for their audience. Even their best songs tend to wander around, stop somewhere unexpected, make a joke, get sad, and then suddenly fucking explode.

“Montreal Rock Band Somewhere” contains almost the entire Happyness proposition in five minutes. It is funny without being a novelty song, melancholy without announcing itself as melancholy, and loose without actually being sloppy. Beneath the Win Butler joke is a genuinely beautiful piece of guitar music made by a band that understood exactly how much room a song sometimes needs.

They never became Arcade Fire. Good. I’ll take Happyness every day of the week.

15. (T) Crushed Out — Bad Moves

17. Caribbean Wind — Bob Dylan

18. (T) Center of Asia — Paul Pena 

19. (T) 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.

20. 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.

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.

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

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 dont 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 hasnt 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 dont 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 doesnt 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

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.

I Have a Crush on Katie Park From Bad Moves

Epigraph:

Could you read between the lines
Or was it just so obvious?

Bad Moves

New Note: This is an older piece, however I am re-releasing it here. I recently shared a longer piece about some aspects of my life, including, quite centrally, music, so this seemed like a good time.

As with anyone’s story, there are layers to mine. One pretty big layer is when in 2018 I traveled to New York/ Brooklyn, Boston, Philadelphia, and Washington D.C. to see the band Phosphorescent. I saw Phosphorescent four times total on their C’est La Vis tour and they were amazing. I bought a sweatshirt from the merch table and the merch gal told Matthew Houck, the lead singer, about me because I told her I’d come all the way from Japan to see the band. He came down from the stage and gave me a big bearhug, not once but twice at two of the shows. He knew I was going through it, and I needed a hug. He’d been through it too, big time, before and when he was writing Muchacho a few years prior.

As I was seeing Phosphorescent I also took the opportunity to see a few other bands. I saw Yo La Tengo twice at the Borwey Ballroom, Jay Som in Boston, and most memorably The Hold Steady twice at the Brooklyn Bowl where they were playing a three night set. The opener for The Hold Steady was a band called Bad Moves. I had never heard of this band, however, and I don’t say this lightly, they put on a better show than The Hold Steady. Now an opener should try to do just this, to “steal the show,” so to speak. A Bad Moves stole it big time. I was enraptured by their lead singer Katie Park, and met her at the merch table which she was running, which is recounted below. My friend I met at the shows, Austin, pushed me to check out their album Tell No One in depth, which I did, and I loved it. On the train from Washington D.C. back to New York I wrote the first version of this piece, which has been fairly extensively edited since then. This is my sneaky favorite piece, maybe not my best, but you can be the judge. Here it is:

I love live music. More than that, I love live music fans, and music fans in general. This piece is basically about being a music fan, and was inspired when I saw the band Bad Moves open for The Hold Steady in 2018 at the Brooklyn Bowl. They were touring on the back of their first full length, Tell No One. While at the Bad Moves/ Hold Steady show a music geek introduced me to a band called Swearin’. Swearin’ has been around a little longer than Bad Moves, and in 2018 had released Fall Into the Sun. The two bands don’t really sound all that much alike (Bad Moves is basically “Power Pop” and Swearin’ is basically “Indie”) but they write somewhat similarly about matters of love and friendship.

Let’s play a game that we live in a world where a record by a band like Bad Moves or Swearin’ would produce radio hits. I want to live in that world. Or maybe I don’t; maybe it’s better for everyone that bands like these stay a little more on the DL. Let’s first take a look at Fall Into the Sun. (Swearin’s frontwoman is Allison Crutchfield, and the band is mostly her baby.) My pick for the single would be the lead off track, “Big Change.” 

The song opens with this soft-spoken reminiscence — basement shows, empty cans, old romances, long nights of half-drunken idealism. Crutchfield sketches a friendship held together by music, chaos, and the sense that they’d accidentally stumbled into their own mutant little world.

I really like what Crutchfield does here. She is basically writing about a friendship solidified over a shared love of music. Now, I know a lot of people. I also have some friends. When you ask an adult, “How many real friends do you have?” the number will vary widely. A lot of people will say “four or five,” something like that. People in general have surprisingly few real friends. I have ten or fifteen, maybe more, but am only in regular contact with about half that number. A good friendship, in my opinion, is one where no matter how long you and your friend have not hung out, if you see them it’s as if not a day has passed. With this sort of friend, I’ve found, there is between yourself and them something fundamental shared. It can be anything really. For example, I first met my good buddy when we were both in graduate school in Arizona, and at first I thought he was a total dick. He was loud, interrupted people constantly, and loved being the center of attention. One night we were drinking as a department and he started razzing me there on the street, just casually insulting me left and right. Suddenly I got where he was coming from. This was, in fact, his way of offering to be friends. Once I understood this, I began to give it right back to him. Called him every name in the book. And he ate it up. By the end of the night we were fast friends and have been ever since, because we share an understanding that our friendship is based, in part, on ripping on each other. Music, obviously, is another great basis for a friendship.

When Crutchfield sings “no art degree, no conservatory/ just Katie and me,” I’m reminded of the refrain from Don DiLillo’s Underworld: “who’s better than us.” If they can do it, why not us? Fuck ’em. That’s what attitude looks like kids–take notes.

So “Big Change” is my single from Fall Into the Sun. (“My single” here just means the song I would choose as the single. For some records, the single is super obvious, while for other records it’s debatable. Bands and producers, in my opinion, do not always get this right.) A good record will tend to have at least two singles; three is a bonus.

For Fall Into the Sun’s second single I’ll go with “Grow into a Ghost.” It opens with a chugging guitar riff with an almost Krautrock drum line. The song is a perfect 3:10–in and out. Do you know anything about lost love? Swearin’ does.

Midway through the record, she writes to an old love with that drifting, half-in-the-desert melancholy she does so well — remembering who she’d been before they met, watching someone fade into absence until they feel more like a ghost than a memory.

Swearin’ is good, but Bad Moves is better. And the star of Bad Moves is the exquisite Katie Park. (I know they are a collective, but my world is my world baby.) Before their show Katie was at the merch table selling…magic eye! That she made by hand. And what did it say? The magic eye said “Bad Moves.” Obviously. I checked it out and chatted for a few minutes with Katie, trying to play it cool. It was the highlight of my year. 20 minutes later she and the band were on stage, crushing it.

The single here is pretty easy. It’s “Crushed Out.” The band released “Crushed Out,” “Spirit FM” and “Cool Generator” as the singles, all of which are excellent. Maybe “Spirit FM” is catchier than “Crushed Out”? Possible. But “Crushed Out” has more lasting power in my opinion. “Crushed Out” is about exactly what it sounds like. It has a basically perfect power pop structure with a killer hook, a classic bridge, and a theme at once super obvious and super deep–the power of a crush.

The whole song is a tumble of infatuation — that feeling where you can’t focus, can’t think straight, and every look or scribbled message feels like it should be obvious to the other person. It captures the power-pop rush of a crush so clearly it almost stings.

Baby, if you are crush-prone that power never goes away. Bad Moves knows this–it’s kind of what the record is about. Crushing out that way can be pretty obvious–do you think I’m crushing out on Katie at all? Nah, this is just a piece of music appreciation.

Cool Generator is my second favorite song on the album, but my “sneaky favorite” is “Missing You.” A sneaky favorite is just what it sounds like: it’s that song that may fly under most people’s radar but that you have a special soft spot for. My all time sneaky favorite song is “Three Drinks” by Craig Finn of the aforementioned Hold Steady. “Three Drinks” shows up on Finn’s 2016 EP Newmyer’s Roof. It’s nearly acoustic, unlike most Hold Steady songs, and sounds just a little bit country. Three Drinks is about a woman (most great songs are) who may have been a child star once upon a time, and is now a drinker. It is an example of a certain type of song that Finn is amazing at, the deeply empathetic look at adult relationships in all of their gloriously flawed complexity. In this sense, Three Drinks fits in with “Spinners” from The Hold Steady’s 2014’s Teeth Dreams, “Tangletown” from Finn’s 2017 solo record We All Want the Same Things, and “Esther” a Hold Steady single from 2018. Finn’s writing on Three Drinks and Tangletown is at its absolute apex. 

“Three Drinks” delivers Finn at peak empathy. A woman with a messy past drifts through a hotel lobby filled with minor disasters, trying to hold herself together until that magic window — the hour between the third drink and the one that tips the night over the edge. Finn nails that space between fear and transcendence where people feel briefly holy.

The refrain focuses on that magic hour between drinks 3 and 4, when matters begin to move from the slightly anxious first stage of the evening to something entirely other:

So anyway, my sneaky favorite on Tell No One is “Missing You.” The song starts like the others, high-speed power pop, and after two verses switches to a near-spoken word breakdown of the tug-of-war between a crush and the expectations of the world around. Guess which wins?

“Missing You” turns into a spoken-word confession halfway through: the push-and-pull between what the world tells you not to do and the crush that keeps winning anyway. It’s simple rhyming, almost naive, but devastatingly effective.

I officially support these sentiments. .

So that’s my sneaky favorite –doesn’t mean it’s better than “Crushed Out” (it isn’t) it’s just a little sneaky. I’m all about sneaky babes and sneaky favorites, on all levels.

In addition to the Magic Eye, Bad Moves also engage in a little publishing. A little literature. Specifically they publish a pamphlet called “The Virtues of Wearing White.”

Chatting with Katie, she acknowledged more than a passing familiarity with the literature of the Jehovah Witnesses. I love Witness literature. Both Witness and Bad Moves publications have a real “it’s gonna be a bright, bright sunshiny day” vibe. If you know me this is not a secret, but I’m a hardcore closet New Ager. There, secret’s out. I’ve messed around with all kinds of New Age action. Once I attended a Kabbala meetup in Manhattan. There were some hardcore New Agers there too, seriously. Those folks were not in the closet at all. Shining eyes, whatever color they are wearing. Me, I like black because it’s easier to launder, but Bad Moves have me thinking. (One other publication you should take a look at if you are into this kind of thing is the Christian Science Monitor. It’s a serious piece of literature. God is great baby, god is great.)

When I was younger my parents had a friend called Tom Hutchinson, who, predictably, went by “Hutch.” Hutch owned a boutique coffee shop there in town and I drove a delivery van for him for a bit. But that’s another story. Anyway, Hutch was a weird guy and he hated the Witnesses. It was one of his favorite topics. He’d call them the “Witlesses,” and say: “When they come to my house I turn the hose on ’em.” People thought this was pretty funny, but I was not that into Hutch’s attitude to the Witnesses. I mean, he didn’t want anyone trying to convert him on his property, which is fair; however, I felt, and still feel, that if someone wants to come to my door, give me a little literature, and talk about how god loves me I’m gonna let them. I genuinely like the Witnesses. They seem like lovely people. Read more