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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

Read more

On Being Early to Shows

Note: Getting to shows early, I realized, isn’t really about beating the crowd but about entering the space before it hardens into an event—when the room is still provisional, the bartender relaxed, the band half-mythical figures moving casually through soundcheck, and the whole night feels less like a performance and more like something forming in real time; you notice the lighting before it matters, the empty floor that will later surge, the stray conversations, the merch table still untouched, and sometimes—if you’re lucky—the musicians themselves, unguarded and human, which subtly rewires the experience so that when the set finally begins you’re not just watching a show but inhabiting a continuum that started hours earlier, a private prelude that rewards patience, sharpens memory, and turns what could have been just another concert into a small, self-contained narrative of anticipation, proximity, and the quiet pleasure of being there before everything becomes official.

Epigraph
“There’s a thin line between a guy with a backstage pass /
and a guy walking around with his gut hanging out like a jackass.”

— Sun Kil Moon, “Ben’s My Friend”

I’ve always been fascinated by the green room. First of all, why green? They can’t all be green. Second, there’s the whole rider situation. The rider is where things get really interesting. I think it was Van Halen who had in their rider that all the brown M&Ms had to be removed from a bowl. This sounds totally bizarre, but the point was attention to detail. If the venue screws up the M&Ms, they might screw up something much more important, like stage rigging or pyrotechnics. The M&Ms were just a test.

Other riders go in different directions. Iggy Pop reportedly asked for things like a Bob Hope impersonator and other surreal odds and ends, more like performance art than hospitality. Meanwhile Beyoncé is famous for highly controlled riders: temperature, lighting, water, environment, everything calibrated. One approach is chaos, the other total control. Both happen in the green room, which most of us never see.

My first concert was Dire Straits in Pullman, Washington, in a big arena. I was nowhere near the green room, of course. Most of us aren’t. So the real question becomes: what happens before the show, if you’re not backstage?

One answer came when I saw They Might Be Giants in Spokane with my friend Kelly Rudd. Kelly told me his cousin was in the opening band. They got paid twenty bucks for the show. The whole band. Twenty dollars. Totally unbelievable. Outta fucking control. TMBG were already a pretty big indie band, “Birdhouse in Your Soul” had been a hit, and I liked “Istanbul (Not Constantinople)” quite a bit. But after hearing that story I never quite looked at them the same way. The green room fantasy took a hit. Backstage wasn’t glamorous. It was twenty bucks and a handshake.

Another time I went to see Cat Power at the old Club Quattro in Osaka. I got there early, of course, and there was an opener dressed like a fairy with fuzzy, messed-up hair who sat down at the piano and proceeded to play dirge after dirge for what felt like an hour. Solo piano can be great, but this was brutal. I honestly thought I might have to cap myself. At some point I checked my ticket just to make sure this wasn’t actually Chan Marshall. It wasn’t. Thank god.

Then Chan came on and instead of playing from the stage like other artists do, she wandered through the crowd with a wireless mic, half-rapping, half-singing, talking, improvising. It wasn’t really a concert. It was more like some kind of performance art happening. Totally outta control. If I’d come late I would have missed the whole bizarre prelude. Being early meant enduring the dirges but also getting the full weirdness of the night.

Another early-arriver adventure came when I saw Deerhunter at the Hostess Club Weekender. These shows started early and stacked openers all day long. I once saw Mogwai at one of these and had to leave after fifteen minutes because I was hungry, tired, faded, and they were boring the living shit out of me. It happens.

The Deerhunter show in Osaka was even more outta control. The headliner was scheduled for 7 PM, but there were something like six openers. One of them was Ivo Watts-Russell of 4AD, a legendary figure, but he droned on so long that by the time Deerhunter came on they only had about forty minutes. Bradford Cox introduced him with dripping sarcasm, emphasizing “LABEL BOSS,” clearly taking the piss because the band’s time had been cut. I ended up having to see them again months later in Nagoya to get the full set. That’s the risk of being early: sometimes the openers eat the show.

The flip side came when I saw The Hold Steady at the Brooklyn Bowl in December 2018. I arrived two hours early, ate a hamburger, and smoked up outside. That’s where I met Austin, a total Steadyhead. He knew everything: lineups, labels, deep cuts, all of it. We talked music, smoked, and waited. When doors opened we grabbed territory near the stage with the other early-arrivers, a semi-cliquey group of diehards.

Later, when Austin wanted to get back to the front for the encore, he told me to follow him. He moved through the crowd at a half jog and the people parted in front of him like he was Barry Sanders hitting holes. Seconds later we were hugging the stage. I knew then I was in the presence of greatness. I also knew he was my friend. I didn’t get the VIP meet and greet, but getting there early gave me something better.

My one true VIP experience came when I saw The Afghan Whigs in Amsterdam in 2017 at the Paradiso Amsterdam, a beautiful converted church. I arrived three hours early, met Greg Dulli and the band, took photos, bought merch, and watched soundcheck with maybe fifteen people. They played “Going to Town” acoustically, which was a revelation. Later they crushed the full electric set, ending with “Faded.” I paid fifty bucks for that meet and greet and it was completely worth it. Being early paid off directly.

Getting to shows early, then, is not really about the green room at all. The green room is a kind of fantasy—green walls, bowls of M&Ms, riders with impossible demands. Most of us never see it, and even when we do, it turns out to be smaller and more ordinary than imagined. And probably not even green. The real action happens in that strange in-between space before the show: the smoking area, the empty floor, the long wait while the openers drift on and off.

If you arrive early, you get all of it. You get the terrible fairy-piano dirges and the label boss who drones on too long. You get the moment of doubt when you check your ticket and wonder if this could possibly be the headliner. You get the rail territory battles and the cliquey early crew. You get the conversations with strangers who turn into temporary friends, like Austin, who parts the crowd like a halfback and gets you back to the stage in seconds. You get the soundcheck if you’re lucky, the acoustic revelation, the quiet before the storm.

Most of all, you get time. And time at a show is a funny thing. Once the lights go down, everything compresses. The band plays, the songs blur together, and before you know it the encore hits and everyone spills out into the night. But if you were there early, the show feels bigger. It has a beginning, a middle, and an end. You saw the room empty and then full. You watched the night assemble itself.

So while some people drift in late, grab a drink, and wait for the headliner, I’ve always preferred the long route. Get there early. Kill time. Smoke a cigarette. Talk to whoever’s around. Endure the openers, good or bad. Maybe you meet someone. Maybe you don’t. Maybe the band walks through the room. Maybe nothing happens at all. But every once in a while, if you’re lucky, something does. And that, in the end, is why I like to be early to shows.

Dedication:

For music lovers everywhere. You are my tribe baby.

The Adventures of the Thin Man and Andrea Available Now!

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

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

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

Matt

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.

Craig Finn on Nightlife and Adult Relationships IV: Sixers

Note: This short reflection began simply as a reaction to hearing “Sixers” from The Price of Progress by The Hold Steady. Over time, however, it became clear that the song belongs to a larger lineage in Craig Finn’s writing: the quiet, observant songs about adult relationships that never quite come together.

Listeners familiar with Finn’s work will recognize echoes of earlier pieces such as “Spinners,” “Tangletown,” “Esther,” and especially “Jessamine,” where a brief encounter carries emotional weight far beyond its duration. What interests me most about these songs is not romance itself but the fragile moment where two people briefly imagine a connection that may or may not exist.

“Sixers” captures that moment with remarkable economy. Like many of Finn’s best narratives, the drama unfolds not through big revelations but through small gestures, passing observations, and the social physics of an evening that slowly runs out of momentum.

The song feels unmistakably rooted in the atmosphere of the pandemic and its aftermath—a period when many people were cautiously trying to reconnect with the world after long stretches of isolation. In that sense the characters in “Sixers” are not unusual figures but recognizable ones: two lonely people improvising a small pocket of companionship inside a quiet apartment building.

That the connection ultimately proves fleeting is not really the point. The attempt itself—the knock on the door, the drinks, the conversation—is what gives the evening its meaning.

I came to The Hold Steady a little late. Around 2016 I first heard “Constructive Summer” and “Sequestered in Memphis” from the 2008 album Stay Positive—probably through the Spotify algorithm, which occasionally earns its keep. That was the gateway. Even though I had missed the band’s original wave of excitement, I quickly made up for lost time and worked my way through the entire catalog.

A couple years later I went deeper and began listening seriously to the solo records by Craig Finn. That opened another rabbit hole. My early favorite was “Three Drinks,” but over time songs like “A Bathtub in the Kitchen” and “It’s Never Been a Fair Fight” began to feel like the real center of gravity in Finn’s songwriting. The solo records are quieter and more novelistic than the Hold Steady albums, and in some ways I’ve come to think they are even stronger.

Around that same time a music-obsessed friend I met at two Hold Steady shows at Brooklyn Bowl told me that if I really wanted to understand Finn’s writing I needed to go back further, to his earlier band Lifter Puller. He was right. Lifter Puller turned out to be a wilder and more manic version of the same storytelling instinct. The songs move faster, the rhymes pile up in breathless clusters, and the characters—people like Nightclub Dwight—feel sketchier and stranger than the ones who would later populate Hold Steady songs about figures like Charlemagne. Tracks like “Nice Nice” and the closing songs on Fiasco are still some of the most exhilarating music Finn ever made.

All of which is to say that Craig Finn has gradually become, for me, the greatest living songwriter—even if I still concede that the all-time crown belongs to Bob Dylan.


What makes Finn particularly fascinating is the emotional terrain he covers. Early Hold Steady songs often dealt with youthful chaos—parties, drugs, Catholic guilt, and the reckless mythology of young adulthood. But over time he has developed another genre that may be even more compelling: songs about messy adult relationships.

These songs usually revolve around people chasing the thrill of a connection even when they suspect, somewhere deep down, that the connection will probably be short-lived. The crush, the fling, the brief dalliance—these impulses are deeply wired into human psychology and deeply embedded in the culture and art we consume. Finn understands that instinct perfectly. His characters repeatedly pursue moments of intimacy that are intense, fleeting, and often slightly ill-advised.

You can hear that theme in songs like Spinners, Tangletown, Esther, and perhaps most perfectly Jessamine. What distinguishes Finn’s writing is the concision with which he captures these emotional situations. Few songwriters are better at compressing an entire relationship dynamic into a handful of lines. In that respect “Jessamine” may be his masterpiece: a small, perfectly observed sketch of longing, timing, and missed possibility.

It is within that lineage that the song “Sixers,” from the 2023 album The Price of Progress, finds its place.


The Price of Progress feels unmistakably like The Hold Steady’s COVID-era record. Finn has described the album as a set of narrative songs about people trying to survive modern life—navigating isolation, economic pressure, technological dependence, and the strange psychological residue of the pandemic years. While the previous album Open Door Policyhad largely been completed before the lockdowns, The Price of Progress was written in the wake of that disrupted period when people were cautiously trying to rebuild their social lives.

“Sixers” captures that atmosphere perfectly.

The entire story unfolds inside an apartment building where two strangers live stacked one above the other. Both are alone. Both are restless. Both are coping with their evenings through small chemical adjustments—beer, pills, and cocktails.

The woman downstairs begins the night with a six-pack from the store down the street and a prescription meant to help her focus her attention. The man upstairs has just returned from another steakhouse dinner with coworkers in asset management, a job that is, as Finn notes dryly, “as thrilling as you’d think.” The two have seen each other before at the mailbox, one of those semi-public urban spaces where strangers develop a faint familiarity without ever truly knowing each other.

The encounter begins with a pretext. She knocks on his door and tells him she thought she heard footsteps upstairs.

The truth, of course, is that she is simply lonely.

Like many Finn songs, the story unfolds in the semi-public spaces of urban life—apartment hallways, mailboxes, shared walls—places where strangers gradually become aware of each other without ever becoming fully connected. Finn has always had the instincts of an urban anthropologist, observing the small rituals and awkward encounters that define city living.

For a while the evening works. They talk about work and school. They discuss how the city has changed. They make drinks in the kitchen—he measures gin while she crushes pills on the counter. At one point he is “muddling the mint,” a beautifully precise detail that captures the strange domestic intimacy that can arise between two people who barely know each other. Soon they are dancing, sending out for takeout, and even sharing inside jokes.

For a few hours the night begins to resemble a small, improvised relationship.

And then comes the hinge of the entire song.

Sunrise into sundown, sending out for takeout, sharing inside jokes now
He finally tries to kiss her and she says that it’s not like that.

With that single line the entire evening collapses.

Everything that seemed like romantic chemistry turns out to have been a misread signal. The connection was real enough to sustain conversation, drinks, dancing, and jokes, but not the kind of connection he thought it was.

One of Finn’s recurring themes is the almost-relationship—encounters where two people briefly imagine a connection that never quite materializes. Songs like Jessamine, Spinners, and Tangletown inhabit that fragile territory. “Sixers” belongs squarely in that tradition.

Finn doesn’t dramatize the moment with an argument or confession. Instead he shows the social physics of awkwardness taking over: everything slows, the conversation falters, and the energy drains from the room.

The next gesture is even more telling.

She cleans off the countertop and says she should probably go.

It is a tiny domestic act, but it carries enormous emotional weight. Cleaning the counter becomes a way of resetting the scene, erasing the traces of the evening before leaving.

Like many Finn songs, “Sixers” tells its story through objects as much as through dialogue. The room fills with small details: the six-pack from the corner store, the pill bottle in the cupboard, the carefully mixed drinks, Sinatra on the stereo, and one quietly devastating observation about the apartment’s décor.

At one point she notices a Nagel poster hanging on the wall in a silver frame and thinks it looks kind of lame.

It’s a perfect Finn detail. In a single line we learn something about the guy’s taste, his slightly square professional aesthetic, and the quiet judgment forming in her mind even while the evening unfolds.

Months later she sees him again in the hallway. This time he is standing with his fiancée, whose name she can’t quite remember—Kelly or Katie.

The moment closes the loop of the story. Whatever possibility once existed between them has long since evaporated. The evening that once felt full of potential turns out to have been only a brief improvisation between two lonely people passing through the same building.

The song ends where it began, with footsteps.

But this time the sound isn’t real.

She thinks she hears footsteps
But now they’re not really there.

The knock on the door that began the story was an attempt at connection. The footsteps at the end are only the ghost of that attempt, echoing in the quiet of her apartment.

Like many of Finn’s best songs about adult relationships, “Sixers” isn’t about catastrophe. Nothing explodes. No one storms out. The drama is smaller and more recognizable than that.

It is simply about lonely people improvising connection in a time of trouble.

And sometimes getting it slightly wrong.

Note: If you like this essay, you may also like the essays below which also deal with the singer-songwriter Craig Finn and his band The Hold Steady.

On the Other City

Note: This piece grew out of a long fascination of mine with what might be called the “night economy” — the network of bartenders, servers, managers, taxi drivers, and late-shift workers who keep a city alive after most people have gone home. If the daytime city is governed by office hours and commuter rhythms, the nighttime city runs on a different clock entirely.

The two figures mentioned here, Haku and Haru, are part of that world in Kyoto. Haku runs the bar at ING and seems to operate on a schedule that would puzzle most daylight citizens, opening in the evening and closing well into the small hours while somehow producing food, music, and atmosphere in a space not much larger than a good-sized living room. Haru manages a shisha lounge in eastern Gion and moves easily between the daytime and nighttime rhythms of that neighborhood, which has its own distinct ecosystem of bars, touts, and late-night wanderers.

The small bar Ishimaru Shoten, tucked down an alley off Pontocho in the Kiyamachi district, serves in the essay as a kind of neutral ground — one of those places where the various inhabitants of the nocturnal city briefly cross paths once their shifts end.

The central idea is simple enough: most cities contain two cities. The first is the one that tourists and office workers see during the day. The second comes into view only after midnight, when the people who keep the lights on, the drinks pouring, and the plates spinning begin their own quieter rounds.

Epigraph:

Last night, I told a stranger all about you
They smiled patiently with disbelief
I always knew you would succeed no matter what you tried
And I know you did it all
In spite of me

Morphine, In Spite of Me


Most people believe a city goes to sleep around midnight. This is not true. Around that time a city simply changes populations.

The day city winds down: office workers, shopkeepers, commuters heading home, lights switching off floor by floor. But another population wakes up. The bartenders. The shisha managers. The taxi drivers. The people who work the strange hours when the streets are quieter but the human drama is often louder.

This is the other city.

If you spend enough nights wandering around it, you begin to recognize its citizens. They are the people who actually know how the place works after midnight.

One of them is Haku.

Haku runs the bar at ING. He opens around seven in the evening and closes somewhere between three and four in the morning. Prep starts around six. By the time the first customers wander in, the night has already begun for him.

He has long greying hair and rotates through a collection of Rolling Stones T-shirts, something like twenty-eight of them. I have never seen him wear anything else. He smokes constantly, drinks Sapporo if he is drinking at all, and otherwise survives on black coffee.

Somehow he produces a full menu in a kitchen that appears to consist primarily of a Bunsen burner and sheer stubbornness.

Haku’s bar has rules. No Japanese music is the main one. The other rule is that the bar itself is reserved for singles. Groups can sit elsewhere. The bar is for individuals who have come out into the night alone.

But Haku’s real gift is music. He reads the room the way a card player reads a table.

If the crowd is German he might throw on Rammstein. If Scandinavians wander in the speakers might suddenly fill with black metal. Australians get The Saints. If I’m there he might put on My Morning Jacket. The world rotates through the speakers depending on who happens to be occupying the stools that night.

Simply and totally the original man.

Another citizen of the other city is Haru.

Haru manages the shisha lounge in eastern Gion, a part of town where the nightlife becomes a little more ambiguous. The streets there are full of micro-touts, men and women both, gently trying to guide passersby into Thai or Japanese dancer clubs. Small space heaters glow outside doorways and mama-sans smile from behind them like patient spiders.

I never go into those places, though the invitations are often persuasive.

Haru opens the shisha lounge most days at noon sharp. If she is not there, someone named B. or a long-haired young guy handles things until she arrives. She tends the charcoal, mixes my Malibu Milk, and quietly extends the session when the official time runs out.

She knows my habits well enough by now that when I head up the stairs she doesn’t assume I am leaving. She knows I am just stepping outside to smoke.

For a long time she existed in my mind simply as the shisha girl, one of the many figures who keep the other city functioning. But then one night I ran into her somewhere unexpected.

The place was Ishimaru Shoten, a tiny late-night bar down an alley just west of Pontocho in the heart of Kiyamachi. Outside the entrance hang bright red, green, and blue lamps that glow like a small carnival in the dark.

I first discovered the place at four in the morning on a very long night. I was broke that evening, absolutely skint, and there was a very aggressive Japanese guy at the bar who clearly believed the entire establishment belonged to him.

The bar woman, who is about forty-five and still hot as blazes, was batting her eyes at me with what seemed like professional enthusiasm. Meanwhile I realized with growing clarity that I did not actually have the money to pay for the large bottle of beer I had just ordered.

But men are predictable creatures.

I understood immediately that if I played my cards right the territorial guy would buy the drink for me. So I joked with him, gave him a friendly punch on the shoulder, made it clear I recognized him as the reigning emperor of the room. He razzed me a little but saw that I was no threat to his throne.

Sure enough, he covered the beer.

I stumbled home to the Royal Park Hotel on Sanjo Street as the sky was turning pale, crashing into bed around five-thirty in the morning.

Weeks later I returned to Ishimaru and found Haru sitting there.

I teased her gently about sometimes opening the shisha lounge five or ten minutes late when she bikes over from home. I suggested she must be hungover. She laughed, not the polite laugh people sometimes use for customers but a bright, real laugh.

She said she was happy to see me.

And that was when I learned her name. Haru.

We talked for a while. I drank a White Russian and ate dashi maki while she sipped something that might have been shochu or nihon-shu. I felt a strange rush of adrenaline the whole time, those goosebumps that run up both arms when the night suddenly opens into possibility.

Not necessarily romantic possibility. Just the larger sense that anything could happen.

Anything can come.

After twenty or thirty minutes she said goodnight and promised we would meet there again sometime. We did run into each other once more about a week and a half later, though the evening remained just as light and brief as the first.

But something had shifted.

She was no longer simply the shisha worker in my mental map of the city. She was Haru, a fellow traveler in the other city.

And that is the thing about the people who live their lives after midnight. They know parts of the city the rest of us never really see. They watch the celebrations and the arguments, the flirtations and the quiet breakdowns. They see who walks home alone and who finds someone to share the long dark streets.

Every city has two maps.

The one everyone uses during the day.

And the other one that only appears after midnight.

Dedication:

For the men and women of the night. Who keep the drinks coming and the plates spinning. It’s a rocky world, and you rock it baby.

Note: If you enjoyed this essay, you may also enjoy the two essays below, which also feature Kyoto and Osaka nightlife in all it’s beautiful glory.

On Some Meetings and Close Encounters with Musicians II

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

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

Epigraph

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

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

— Dire Straits, “Skateaway”

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

Here are a few such encounters.


I. Initiation

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

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

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

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

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

I would later learn otherwise.


II. Revelation

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

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

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

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

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


III. Chaos

Not every show produces reverence.

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

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


IV. Theatre

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

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

Then Cat Power appeared.

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

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

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


V. Ritual

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

It was less a performance than a ritual.

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


VI. Canada Night

Not all memorable shows are mystical.

Sometimes they’re simply loud.

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

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

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


VII. Breakdown

Not every concert goes well.

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

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

The show never recovered.


VIII. Redemption

Fortunately the story has a better ending.

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

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

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

Dedication

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


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

Shotgun in Seth’s Ford Explorer

Note: This piece takes place in Spokane, Washington in the fall of 1991, during our senior year at St. George’s School. CDs were still a relatively new luxury item for teenagers, Zip’s runs counted as real excursions across town, and a hunter green Explorer in the school parking lot could serve as the center of an entire small social world.

Epigraph:

Out with the posse on a night run
Girls on the corner, so let’s have some fun
Donald asked one if she was game
Back Alley Sally was her name
She moved on the car and moved fast
On the window pressed her ass
All at once we heard a crash
Donald’s dick had broke the glass

Ice T

Seth drove a green Ford Explorer, which meant two things: he was always the driver, and John Innes almost always called shotgun.

Ours was a class of twenty-eight boys at St. George’s School, which meant the social landscape was less a battlefield than a small archipelago of cliques. Everyone knew everyone, and everyone more or less supported everyone else. Still, there were natural groupings. Seth, Innes, and I spent a good deal of time together, with Kelly sometimes orbiting the car and Richard Barkley frequently around as well.

The Explorer usually lived in the SGS parking lot behind the lower school. During the day it sat there waiting for the moment seniors could leave campus, which we could do whenever we wanted. When that moment came, Seth’s Jeep became a kind of small republic on wheels.

There were rules, or something close to rules. Seth drove. Innes called shotgun. He cared about it the most and therefore usually got it. Occasionally Barkley or I would challenge him, which would inevitably produce an argument about whether the call had been made properly or whether the timing had been unfair. The exact legal framework of shotgun was never fully settled, but the outcomes were usually predictable.

Inside the Explorer there were CDs everywhere. Not in a messy way—Seth kept the car pretty well—but there were dozens of them, probably stored in one of those large CD wallets that seemed to exist in every car in the early nineties. Seth would sometimes come back from Hastings with six or eight discs at a time. I remember watching those purchases with something close to disbelief. I could rarely afford a CD myself, so when I did manage to acquire something like Tindersticks or Billy Bragg’s Spy vs. Spy, it was a very big deal.

The music rotation in the Explorer was remarkably tolerant. Seth tended to favor Judas Priest and Metallica, while Innes leaned toward Ice-T. Joe Tyllia loved Cat Stevens and so Cat Stevens appeared frequently. I personally preferred Dire Straits at the time, which never quite made the regular rotation, so I generally waited for Warren Zevon or Cat Stevens to come back around. Nobody vetoed anyone else’s music. Whatever disc was in play generally stayed there.

The Explorer had a few regular destinations. State B basketball games were one. Another was Zip’s on the north side of town. Seniors could leave campus whenever they liked, and sometimes that meant simply deciding that a run across Spokane for burgers was necessary. Seth’s house was another stop, as was Hastings, where the CD acquisitions occurred.

Occasionally the driving extended further into the South Hill at night. Sometimes we would pass near Manito Park, though I remember doing those wandering drives more often with a slightly different crew—Dyche, Jonah, Karin, and Lisa. Once that group went to a show by They Might Be Giants, and afterward Kelly reported that the band had stiffed the opening act and paid them only ten dollars. Kelly knew this because his cousin was in the opening band.

The one time I ever took shotgun from John Innes without calling it came on the ride home from the state cross-country meet during our senior year. Our team had finished second by a single point, which felt at the time like the most unfair outcome imaginable. James Johnson had been our first runner, Cam Turner second, and I was third.

When we piled into the Explorer for the three-hour drive back to Spokane, I simply grabbed the seat. No call. No discussion. Just took it. And for that ride home I ran the decks.

For a while Seth’s Explorer was simply part of the landscape of our lives. It sat behind the lower school during the day, appeared at the Coleman house west of the South Hill at night, and carried us between games, fast-food runs, music stores, and wherever else we decided to go.

Then, like most small countries of teenage life, it quietly disappeared

Dedication: For my homies.

On Comebacks and Failed Comebacks III: Amy Winehouse

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

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

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

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

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

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

Amy Winehouse was one of those voices.

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

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

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

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

But the lyrics are something else entirely.

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

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

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

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

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

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

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

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

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

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

Winehouse lived inside that contradiction.

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

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

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

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

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

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

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

Note:

Some Everyday Catalyzed Emergencies

Note: The examples in this piece are drawn from moments in my own life where the structure I call a catalyzed emergency appeared in miniature.

What these moments share is not their subject matter but their pattern. A system—whether emotional, institutional, or social—exists in a temporary equilibrium. Then a relatively small catalyst activates tensions that were already present beneath the surface. Once activated, the situation accelerates and decisions that previously seemed distant are suddenly made in real time.

In each case, the catalytic moment itself was small: a candid remark during a conference break, a humorous but revealing line in a professional meeting, or a single sentence spoken in a social situation. Yet in each instance the effect was immediate. The atmosphere shifted, ambiguity collapsed, and the underlying structure of the situation suddenly became visible.

The personal examples described here are therefore not offered as dramatic events in themselves. Their significance lies in the way they illustrate, at the scale of everyday life, the same structural pattern that appears in larger historical crises.

Catalyzed emergencies, it turns out, are not rare occurrences reserved for moments of world history. They happen quietly and frequently in ordinary human experience.

Once you begin thinking about catalyzed emergencies, it becomes difficult not to see them everywhere.

Most of life proceeds in a kind of provisional calm. Conversations unfold along familiar paths. Institutions conduct their meetings, relationships drift through their usual rhythms, and the tensions that exist beneath the surface remain politely contained. Decisions are postponed. Conflicts are softened by habit. The system holds together because nothing has yet forced it to reveal its deeper structure.

Then something small happens.

A sentence is spoken a little too plainly.
A truth appears unexpectedly in the middle of a casual conversation.
Someone says something in a meeting that suddenly exposes the machinery of the institution.

The catalyst itself is often tiny compared to the shift that follows. Yet once it occurs, the atmosphere changes almost immediately. Decisions that once felt distant suddenly move into the present. The underlying structure—emotional, institutional, or relational—becomes visible.

Once you start noticing these moments, you realize they are everywhere.

I remember one such moment during a conference break with the young woman I call Isobel. We were talking in that loose, slightly intimate way people sometimes do between sessions, when the formal structure of the day has momentarily dissolved. The conversation drifted into unexpectedly personal territory, and at one point she mentioned something about her private life that was startlingly candid.

The remark itself was quiet and almost offhand. Nothing in the hallway changed. People were still pouring coffee, drifting between rooms, checking their schedules. The conference continued exactly as it had a few minutes before.

Yet internally something shifted very quickly.

A boundary that had previously existed only as an assumption was suddenly visible. The emotional geometry of the situation rearranged itself in an instant. It was one of those moments when the surface calm of an interaction suddenly reveals the deeper structure beneath it.

Looking back, it was a perfect example of a small catalyzed emergency. The remark itself did not create the tension that followed. It simply activated something that had already been present but unspoken.

Institutional life produces similar moments, though usually in a different register.

Years ago I attended a meeting where Steve Keegan, then responsible for development at the International Baccalaureate, delivered one of the most unintentionally perfect lines I have ever heard in a professional setting. Attempting to strike a tone of humility, he reassured the room that the organization should not think too highly of itself.

“We are not special,” he said.

Then, after a brief pause that only improved the effect, he added:

“Of course we are unique and special in many ways.”

The room erupted in laughter, not because anyone intended to mock him but because the remark revealed something everyone recognized instantly. Institutions often survive on carefully balanced narratives about themselves—humble yet exceptional, ordinary yet distinctive. When those narratives momentarily contradict themselves in public, the entire room suddenly becomes aware of the structure holding the organization together.

Again, the catalyst was small: a single sentence.

But in that moment the underlying psychology of the institution briefly revealed itself. Everyone in the room could see the gears turning.

The same pattern appears in more personal moments as well, sometimes with surprisingly decisive consequences.

I remember a night when a man was attempting to pick up Mariko. It was the sort of situation that unfolds quietly in bars and restaurants all over the world—nothing dramatic, just two people talking while someone else tries to determine what role they themselves are supposed to play in the unfolding scene.

For a while the equilibrium held. The conversation drifted, the man continued his efforts, and I watched the situation with the vague uncertainty that sometimes accompanies these moments. Was I a bystander? A friend? Something else?

Eventually I said something very simple.

“We’re together.”

That was it. A single sentence. A declaration that had not existed in explicit form until the moment it was spoken.

But the effect was immediate.

The conversation stopped. The geometry of the room rearranged itself instantly. What had previously been ambiguous became clear. The situation resolved itself within seconds.

Looking back, it was another catalyzed emergency. The sentence itself did not create the underlying possibility. That possibility had already been present in the emotional structure of the evening. What the sentence did was activate it, collapsing uncertainty into decision.

The remarkable thing about these moments is how small they often appear at the time. They do not arrive with the dramatic clarity of historical turning points. They slip quietly into the flow of ordinary life—a conversation during a break, a remark in a meeting, a sentence spoken in a bar.

Only later does the pattern become visible.

Most of life feels gradual while we are living it. Days follow one another in a steady rhythm. Institutions maintain their procedures. Relationships drift along familiar channels. The tensions that shape events accumulate quietly beneath the surface, rarely forcing themselves into view.

Then something small happens.

A remark.
A confession.
A declaration.

And suddenly the structure reveals itself.

The catalyst may be nothing more than a sentence spoken at exactly the right moment. But once the reaction begins, the system rarely returns to its previous state unchanged.

Note: This is Part III is our series on the concept of the “Catalyzed Emergency.” You can read the other two essays below.