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Craig Finn on Nightlife and Adult Relationships III: Jessamine (Craig Finn’s Miniature Masterpiece)

Epigraph:

Jessamine must have had some dreams/ but she never really said what they were.

Craig Finn

Note: This is the third entry in my little ongoing series on Craig Finn / The Hold Steady songs that take up nightlife, messy adult relationships, and the long shadows cast by fleeting encounters. Part I and Part II are available. I’ve also written at length about what I consider Finn’s two greatest songs: A Bathtub in a Kitchen and It’s Never Been a Fair Fight.

Jessamine is track 8 off of A Legacy of Rentals, Finn’s 2022 solo record distributed on his own label, Positive Jam Records. It clocks in at a tight 3 minutes and 25 seconds, and once again I am simply overawed by Finn’s concision and his ability to tell a whole story in just a few words. It is my opinion, and I do not say this lightly, that Finn is the greatest short story writer to have ever lived. 

Jessamine tells the story of a three week relationship between the narrator, who we will continue to call C. for convenience, and a goth girl with a need for speed. A Legacy of Rentals contains at least three excellent songs, the crime caper “The Amarillo Kid,” the gorgeous “The Year We Fell Behind,” and Jessamine. I would love to write about The Year We Fell Behind as well, however Jessamine falls neatly into our conceit of nightlife and adult relationships, although this one seems to depict more of a young person’s relationship. Close enough. 

Jessamine is folky and lilting, of a piece with Finn’s later work which tends toward folk and country as opposed to Lifter Puller’s indie fever dreams and The Hold Steady’s soaring rock anthems. The Finn song that it most closely resembles is “Esther,” from a 2018 EP by The Hold Steady which also depicts an intense and short-lived relationship. “The party ended suddenly, suddenly it’s over/ That left me and Esther all alone and getting older/ All alone and getting older smoking in the street/ Now everything is Esther and it’s been that way all week.”

Jessamine opens thusly:

I met Jessamine in Cherry Hill

Her dress all done in daffodils

The sticker on her skateboard said, “Speed kills”

And yeah, it probably did just what it said

Cherry Hill is in New Jersey, where the song is set. Jessamine is probably a younger woman, and a skater. The first verse foreshadows her ultimate fate. Incidentally, the first time I visited New Jersey was junior year of college with my Asian Art History class. It was also on this trip that I first visited New York City, the most intoxicating place on earth which I have written about relatively extensively. I wrote about my Art professor in my piece on my senior year at Hamilton College, in relation to a girl I had a total crush on, called L. L. was not exactly goth, but she might have been goth-adjacent. And she was totally intense. More on goths in a minute.

Verse II adds a little more context.

I only knew her for like three weeks straight

And the whole time we were wide awake

You know “Trenton Makes, the World Takes?”

She had it spray-painted over her bed

It is my experience that short-term relationships can be, probably are, the most intense and intoxicating type of relationships in a sense. The depth that comes with a true crush, while of a completely different valance from a long-term relationship, is, I believe, without parallel. But then again, I’m an action junkie, as is Finn. I wrote about the power of a crush in my Bad Moves piece where I confessed to a serious crush on their lead singer, Katie Park. I actually sent the piece to the band via Instagram, and they responded saying “Thanks for the write-up.” I don’t know, but I like to believe Katie read, or at least saw, my piece! Unfortunately, Bad Moves are disbanding and are, I believe, on their farewell tour.

The wording “three weeks straight” implies that C. and Jessamine were, temporarily, inseparable, sleep deprived, and deep into each other. Trenton is, of course, also in New Jersey, and though I hadn’t heard of the exact phrase quoted until I listened to the song, it is apparently well known locally and appears in neon on a bridge.

Verses III and IV introduce Jessamine’s death obsession, and to me anyway suggest that she is what I would call a kind of a goth.

We used to hang around her room

Getting off on all the gloom and the doom

Watching cavemen in the cartoons

Playing xylophones made out of bones

She was sexy, but still death-obsessed

She said the bloodshed makes such a mess

But you really don’t even have to market it

Yeah, it pretty much sells itself

Now I am not really into a lot of bones and blood personally, but I do like me some goth girls. In fact, in the course of my life I have sort of quasi-dated a few, and for whatever reason they are just my speed. I find goth girls sexy, like Jessamine, caring, and deeply intriguing. And mysterious, of course. I have a weakness for crazy women; I cannot lie. And already I can totally see Jessamine’s appeal.

Jessamine has a number of semi-chourses, and the first one goes like this: 

I should’ve asked her before she departed

How did all these wars get started?

Why do rival crews show up to the same parties

If they hate each other so much?

It’s like they’re secretly in love

Again, we foresee Jessamine’s demise up front. Why would Jessamine have insight into the origins of global conflicts? I’m not quite sure, however the image of rival gangs being secretly in love is oddly compelling. However, it is with the next verse and chorus that the song really gets going.

Verse V and Chorus II go like this:

She said, “Suspicion isn’t wisdom

And the drones look just like doves”

And there was something laying siege to her kingdom

But she never really said what it was

While the incense turned to ashes

And the sunrise was unsure

Jessamine musta had some dreams

But she never really said what they were

Yeah, she never really said what they were

Here we learn that our goth girl heroine has something going on that is unarticulated, or perhaps inarticulable. “Jessamine musta had some dreams/ But she never really said what they were” is such a wonderful and moving line. We all have dreams, I suppose; some come to fruition and some don’t. But Finn is in no way judging Jessamine’s relative inability to describe her dreams; instead this aspect of her character only adds to her obliqueness, her mystery.

The next verse and chorus show that Jessamine in the end, and probably in the beginning, had the upper hand in the relationship.

We kinda ended how we began

With Jessamine meeting a man

And liking that man just a little bit more

Than the boy she had before

I hadn’t even seen her since

I guess this new guy was some kind of prince

I guess his castle was a front for some fence

And then the whole damn city got warm

And they were trying to ride out that storm

Again, Finn is a total master of precision and compression. C. is immature, Jessamine is, to some extent, on the make, her new boyfriend is crime-adjacent (so many of Finn’s songs feature characters on the margins of the legal world), and the whole damn city mirrors Jessamine’s flightiness. The crush is over; C. is dumped and he never sees her again. That’s a weird and kind of almost frightening part of short-lived relationships–while their depths are as intoxicating as anything in life, people will just move on and the moment exists only in memory, burned into the fabric of time, but still fleeting.

The next verse points toward C. getting over Jessamine, and alludes to the idea that what may seem for a time to be a storm will pass; a crush, with all its power, is also somewhat illusory.

‘Cause the rain is inconsistent

And the thunder is insincere

‘Cause it makes a big commotion

But eventually it clears

The next verse and chorus puts a pin in Jessamine’s story, and Finn employs his classic penchant for alliteration along the way. Maybe to get away from the scene, or perhaps for some other reason, C. moves out west, loses his shirt, metaphorically, and literally perhaps, and gets word of Jessamine’s demise.

I went out to San Francisco

And some sailor stole my shirt

I was sitting on the passenger side in a taxi

The first time that I heard

That she was probably speeding

And no one else was hurt

Jessamine must’ve had some dreams

But she never really said what they were

Yeah, she never really said what they were

I love the line here “and no one else was hurt.” It’s hard to fully explain why, but it’s oddly moving that Jessamine, on her way out, with all her attraction to blood and bones, didn’t take anyone with her. Finn doesn’t even really register what C.’s reaction is to Jessamine’s death is, he simply repeats the lines about dreams such that she dies as she lived, unknown to herself and unknowable to others.

Overall, Jessamine might seem like kind of a minor song. It’s short, and maybe doesn’t have the deep metaphorical richness as a song like A Bathtub in the Kitchen. Nonetheless, I love it. My sense is that a writer has to write for years and years before they can get to a song like Jessamine. Finn is a few years older than me, and has accumulated the wisdom and compassion to make a song like this look easy. It is not.

I wish her to say a brief word about AI, which may seem unrelated. The other night I met up with a few friends and some friends of friends were there as well. One of them, a slightly older gentleman who used to work in tech, started talking about how much he loved AI music, especially some kind of mash-up of two well-known bands. I appreciated that fact that he liked this “music,” but I have to confess that I could not have cared less. The idea of AI music, especially music with lyrics, interests me not at all. And this is, essentially, because I like people better than machines, but also because I don’t think AI, at least at this point, can come close to writing a song like Jessamine. I won’t get super political here, however the idea that AI can replace, or even duplicate a Jessamine, or Return of the Grievous Angel by Gram Parsons, or Come in from the Cold by Joni Mitchell, for example, just seems absurd to me. As implied above, Finn had to live 50 years, listen to tens of thousands of songs, and write hundreds to get to Jessamine. At 3 minutes and 25 seconds it is a mini-masterpiece.

Dedication:

For goth girls everywhere.

Note: If you enjoyed this piece you might also enjoy the pieces below, which also cover the singer-songwriter Craig Finn.

Craig Finn on Nightlife and Adult Relationships I: Most People are DJs
On Subcultures and Scenes in Craig Finn’s “It’s Never Been a Fair Fight”
On Craig Finn’s “A Bathtub in the Kitchen”
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Scenes from Hamilton College III: Sophomore Year I (with cameos from Sonic the Hedgehog, Ani DiFranco, and Candle Time)

Note: In Part I and Part II of this series I wrote about my freshman year at Hamilton. Part III will take up sophomore year where I lived down the hill in Bundy Dorm.

All you ladies and gentlemen
Who made this all so probable

Big Star

After freshman year I returned back to Washington State for the summer. I have written glancingly about this period, suffice it to say I was not up to much. Still broke, I did have a short lived girlfriend but she dumped me mid-summer. I spent a few days moping around playing nerf golf at my parents’ house, then got over it. I don’t remember much else from that summer except that I got back in good running shape, and when I got back to campus in the fall I turned out, once again, for the running team.

One thing I neglected to mention in my pieces on freshman year is that I actually competed on the JV running team at Hamilton for a time and ran a few races. I was not in great shape that year, and JV was not that exciting. As I have written, I had other pursuits. Sophomore year, however, I was in better shape and had a shot at making the top five. The only other runner I recall was called Harry. I thought Harry lived in Sig, but Jake tells me he was in a frat called THX, about which I remember nothing. In any case, Jake knew him. Harry was a hardcore runner and scolded me about my lifestyle, wanting me to devote myself to the team. I was not going to do this, but I was able to run with Harry and the first team for a number of practices. In the long run though it didn’t work out–they ran mornings and afternoons, and my summer shape wasn’t going to carry me through a hyper-competitive season. I was a good runner, but I just didn’t have the drive. Sooner or later I left the team, this time for good. I look back fondly on Harry however–he was right; I was lazy and needed a kick in the rear.

As a sophomore I roomed in a double with John Innes (there were two John’s in my friend group, John Innes and John Slack), in a dorm halfway down the hill to Clinton called Bundy. Marc Campbell was also on our floor. Ian was living in his frat, but spent a lot of time in Bundy as he was dating Ann, someone who I became close with over the year as well. Jake was over at Sig and I didn’t see much of him, mostly for geographic reasons.

Bundy was a way different story than North. First, I spent a lot more time in my dorm room with John Innes. Innes would watch the soap opera Days of Our Lives and insist I watched it too. I could have cared less, but watched it to be a good friend. We also played Sega, almost exclusively Sonic the Hedgehog and Sega Hockey, at which John usually beat me (however not in the biggest matches, as I’ll get to later). Innes liked rap music and had a pretty good collection. I could get into some of the rap; I liked Public Enemy, KRS One, De La Soul, and a minor band called Basehead which wasn’t really rap. However I was by then deep into what would today be described as alternative or indie music, so Innes’ taste and mine mostly diverged. We were both good about sharing airtime though, so he got to know my music and I his.

The record I listened to the most, by far, that year was Big Star Third: Sister Lovers from the then mostly forgotten American band Big Star. I loved this record (which was on Rykodisc), and played it endlessly while trying to advance in Sonic the Hedgehog. I stuck my mattress in the closet and hung a tapestry over the door area so I had a little cubby to sleep in. Overall, the whole scene was much more domestic than the pretty chaotic North.

Other than Marc and John Innes, I don’t remember exactly who the other guys who were on our floor, but I’ve been reminded that John Slack was one of them. Ian and Jake were living in frats, and over the year I got to know a new crew of people, including several girls. These included firstly Jenny and Jen, who lived in the female area on our same floor (maybe the second floor? Innes will remember). Innes and I became very close to Jenny and Jen, and spent almost every evening hanging out in their room doing something called “Candle Time.” Candle Time was pretty much exactly what it sounds like–we would turn down the lights, light candles (which was probably against school rules) and talk for hours. We would talk about our days, people and goings on in the dorm, and just life in general. It was really wholesome and again, a major change from North.

Candle Time lasted, in my recollection, for a number of months, but not all through the year. Despite spending so much time together, there was no romantic involvement, although I believe Innes and Jen did get together later, and briefly; I’m not really sure. I think it was supposed by some that I myself had a crush on Jen; however although I liked her a lot this was not the case. I did have a little bit of a crush on Jenny, but she had other people who were interested in her and we all hung out so nothing ever happened. That was fine–it was actually really nice to just have close female friends with no expectations.

Jenny and Jen were both from the upstate New York area, broader Rochester as I recall. My guess is they came from relatively less money than many of our classmates, who came from preppier areas, and schools. I actually visited Jenny’s house once or twice, and I think a bunch of us slept over once and watched the film Glengarry Glen Ross. These included Amy Holland, who was one of the coolest chicks around. She was called “Red,” on account of her red hair, and was totally my speed. Everyone else fell asleep during the movie except Amy and I and as I recall she loved what is, to be fair, a pretty stereotypically male film.

Jenny’s house was nice, but seemed pretty middle-class and maybe that’s part of why we all bonded–the richer kids, although I obviously hung around with them a lot, had their own life ways to some extent. I remember one evening Jenny and I went to see the band The New Dylans on campus. I thought they were a good band, and had found their cassette at the campus radio station where John Innes and I had a sports talk show. Their record has a song I liked called “The Prodigal Son Returns Today.” They sounded kind of like a minor league Big Head Todd and the Monsters or something, and are kind of dated today if I’m honest, but I was excited for the show. At first it was pretty full, but people left little by little and by the end it was just me and Jenny. The band played their hearts out for the two of us, including encores! After the show, I joined them for a cigarette outside and chatted. I told them that I really liked the show and they said thanks and all with no mention of the fact that the venue was totally empty. That’s professionalism, I thought, and I imagined that as a band trying to break through playing small colleges and sending cassettes to radio stations they’d had their share of ups and downs. I doubt they are still around, but if so I’m rooting for you guys!

A bigger star that played Hamilton was Ani DiFranco. I saw Ani several times, both on campus and off, as she was pretty huge in New York State at the time. She had not yet released “Dilate,” which came in 1996 and was her mainstream breakthrough to the extent she ever had one, but she was a star on campus, mostly with the women but with a lot of the guys too. Ani put on a great show, and I totally got the appeal. She was kind of the Jeff Rosenstock of the day I suppose.

Shawn Colvin also came, and I knew some of the people who were assigned to take care of her backstage. They reported that she was a total asshole, asked for coke, and generally threw her weight around big time. Shawn Colvin was OK, but no so great that she could act like a diva I don’t think. Full on divas are acceptable-like Joni Mitchell might be a diva and what are you going to do–but minor league divas pretty much suck.

Anyway, like I say over the year although we still saw each other, I saw less of Jenny and Jen, and more of other people like Ann, Amy, and Matt Thornton. I’m not sure where Matt lived, maybe Bundy and maybe not, and I don’t recall either how or when I met him, but we soon became fast friends. Matt was full speed ahead, and argumentative, but I can handle my own in an argument, and I really liked him. Matt ran with an interesting group of friends, including several Asian-Americans who I believe lived on the Kirkland side of campus. Hamilton used to be a guys’ school and Kirkland was the attached girls’ school. Then at some point they merged, but the Kirkland side and the old Hamilton side always felt distinct to me and were separated by a bridge.

One time we were talking about going to New York and Matt told me about some clubs for Asians that he was interested in. Matt’s friends told him that he (or I) could not go to these clubs because we would get the shit kicked out of us. Had to be at least half-Asian apparently. But I think Matt went to these kinds of clubs anyway and did not get beat up, because he just sort of rolled that way.

Matt and I and Ian did go to New York eventually, and spent a few days uptown at some person’s apartment where I commandeered a prime sleeping space and we ordered pizza three times a day. I believe this was actually after graduation, as Matt transferred before graduating from Hamilton.

As I mentioned in an earlier piece, this was also the year Ian and I went to Boston to see music shows. We went with a fellow called Cale who was a freshman. Cale was cool, and also we liked him because of his name, reminiscent of John Cale, violist for the Velvet Underground who Ian and I were both fans of. With Ian and Cale I felt like I was in good company–we were all very simpatico.

My academic performance sophomore year was just OK. I took more English classes, and also started to take some History classes including some Asian History with Tom Wilson. Tom Wilson was a good professor, but I think he was one of those guys who really saw himself at U. Chicago or Yale or something. A lot of academics are like that. Nevertheless, Tom was good–tough but fair–and pushed me to really deepen my research abilities. Outside of Tom’s class, my effort was a little mixed, and during the dead of winter I skipped some morning classes because the climb up the hill was just too tough. The winters in upstate New York are pretty brutal, and I preferred to stay local down in Bundy a lot of the time.

One more thing I remember from this year is starting, and then dropping, photography class. I had an old camera that barely worked, and was interested in learning how to develop film in a darkroom. However, photography class was really expensive because we had to regularly buy these huge rolls of film which cost like $50 at the school store. A classmate I’ll call C. to protect his identity told me, “just tuck your pants into your socks and drop the film down your pants and walk out. That’s what I do.” But I wasn’t going to steal film all year and there was no way I could pay the outrageous costs. On top of that, I wasn’t all that good–certainly my classmates outclassed me, crappy camera or not. So I dropped it after six weeks or so; however now that I think about it I may well have met Matt Thornton in that exact class. It’s a possibility.

Note: That will do it for Part III. In Part IV I’ll write more about my friendship with Ann as well as the Sports Talk Show we did on the Hamilton radio station.

Dedication: For the whole Bundy dorm, actually. It was a pretty chill year.

to be continued…

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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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.

Craig Finn on Nightlife and Adult Relationships I: Most People are DJs
Craig Finn on Nightlife and Adult Relationships III: Jessamine
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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.

Tuesday Kyoto Bar Crawl
The Night of Fucking Adam
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On Some Meetings and Close Encounters with Musicians II

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

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

Epigraph

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

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

— Dire Straits, “Skateaway”

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

Here are a few such encounters.

I. Initiation

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

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

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

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

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

I would later learn otherwise.

II. Revelation

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

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

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

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

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

III. Chaos

Not every show produces reverence.

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

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

IV. Theatre

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

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

Then Cat Power appeared.

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

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

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

V. Ritual

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

It was less a performance than a ritual.

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

VI. Canada Night

Not all memorable shows are mystical.

Sometimes they’re simply loud.

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

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

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

VII. Breakdown

Not every concert goes well.

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

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

The show never recovered.

VIII. Redemption

Fortunately the story has a better ending.

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

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

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

Dedication

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

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

On the Four Times I Met Yo La Tengo
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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.

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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:

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In Defense of Mayo Thompson

Note: This essay reflects on the artistic approach of Mayo Thompson and the work of Red Krayola, particularly the band’s deliberate challenge to conventional ideas of musical skill. The famous observation that Thompson plays the guitar “badly, on purpose,” often cited in critical discussions of the group’s work — including later reassessments of records such as Malefactor, Ade — captures something essential about that approach.

The phrase can sound dismissive at first, but it also points toward a deeper artistic intention. From the late-1960s underground scene through later recordings, Red Krayola consistently treated rock music less as a polished craft than as an open field for experimentation. Imperfection, disruption, and instability were not accidents but part of the aesthetic design.

Whatever one ultimately makes of the results, Thompson’s work continues to raise an interesting question: how much of what we call musical “skill” is simply a set of habits that artists occasionally need to break.

There are certain musicians whose reputations survive largely through footnotes. They appear in the histories. Critics cite them as influences. Other artists speak their names with reverence. Yet relatively few listeners spend their evenings actually playing the records.

Mayo Thompson, the guiding figure behind Red Krayola, occupies precisely that strange territory. His band is frequently described as “important,” “experimental,” or “avant-garde,” words that often function as polite signals that the music itself may not be especially enjoyable. Red Krayola records circulate through the culture like curious artifacts — admired, studied, but approached cautiously.

And the most famous criticism of Thompson’s musicianship captures the problem perfectly.

A critic once observed that Thompson plays the guitar “badly, on purpose.”

The line, often repeated in retrospective discussions of Red Krayola’s music, originally surfaced in commentary surrounding the band’s 1989 record Malefactor, Ade. Whether in a Pitchfork reassessment or earlier critical recollection, the phrase stuck because it seemed to summarize the entire aesthetic in five devastating words.

Badly. On purpose.

For many listeners the sentence reads like a dismissal. But read another way, it becomes the most accurate description of Thompson’s artistic method ever written.

Because the key word in that sentence is not badly.

It is purpose.

From the beginning, Red Krayola treated rock music not as a set of rules to master but as a field of possibilities to disrupt. When the band first appeared in the late 1960s, rock was rapidly developing its own conventions — tighter songwriting, increasingly polished production, guitar virtuosity becoming a badge of seriousness. Thompson responded by moving in the opposite direction.

Instead of improving technique, he destabilized it.

Instead of polishing songs, he dismantled them.

Instead of reassuring the audience, he occasionally seemed to provoke it.

To understand this impulse, it helps to remember the strange cultural environment out of which Red Krayola emerged. The late-1960s underground was full of what might loosely be called the freak scene — a loose constellation of psychedelic bands, communal happenings, and avant-leaning musicians who were less interested in building careers than in testing the boundaries of sound itself. In Texas, where Red Krayola formed, that scene intersected with the surreal humor and anarchic spirit of the local counterculture. Musicians were experimenting with noise, collective improvisation, and absurd theatrical gestures long before those practices acquired respectable academic labels.

Red Krayola fit naturally into that environment. Early performances sometimes resembled happenings more than concerts. Songs dissolved into noise. Improvised ensembles wandered across the stage. Audience expectations were occasionally disrupted on purpose. It was not chaos exactly — more like a deliberate challenge to the idea that a rock performance had to behave in a predictable way.

Thompson understood something fundamental about rock music that many technically superior players missed. The genre had always contained a certain productive roughness — a willingness to accept imperfection as part of its expressive vocabulary. Chuck Berry’s guitar was not elegant in the classical sense. Early garage bands could barely tune their instruments. Punk would later turn this roughness into a formal principle.

Red Krayola pushed that principle further than almost anyone else.

By “playing badly on purpose,” Thompson exposed the hidden assumptions behind musical skill. What does it actually mean to play well? To hit the expected notes? To follow the established structure of a genre? To demonstrate control over the instrument?

Or might it mean something else entirely: the ability to reshape the instrument so that it produces new kinds of thought?

Listen carefully to Red Krayola’s recordings and the supposed incompetence begins to look suspiciously intentional. The guitar lines wobble, fragment, and reassemble themselves in unexpected patterns. Rhythms appear and disappear. Melodies emerge briefly before dissolving into something stranger. The music behaves less like a traditional composition and more like an argument unfolding in real time.

The phrase “avant-rock” is often used to describe this territory, but the label can make the music sound colder than it actually is. Beneath the disruption lies a restless curiosity about what rock music could become if freed from its habits. Thompson’s playing does not reject the guitar so much as treat it like a tool for questioning the very idea of guitar playing.

Which brings us back to that famous line of criticism.

“Playing the guitar badly, on purpose.”

For some listeners the sentence still reads as an indictment. But for others it begins to sound like a manifesto. What if the deliberate abandonment of technical mastery allows a musician to explore new expressive territory? What if awkwardness becomes a form of freedom?

The history of experimental music is filled with similar gestures. Artists deliberately violate the rules of their medium in order to discover what lies beyond them. Painters distort perspective. Writers abandon traditional narrative structure. Filmmakers fracture chronology. Thompson simply applied the same logic to the electric guitar.

And the results, while sometimes difficult, have proven surprisingly durable. Decades after Red Krayola’s earliest recordings, the band’s influence can be heard echoing through the strange corners of indie rock, post-punk, and experimental pop. Musicians who grew up absorbing Thompson’s restless attitude toward form learned an important lesson: rock music does not have to choose between intellect and instinct. It can contain both.

Thompson himself has often downplayed his role in the process, describing music as merely a “means to an end.” That humility is part of the puzzle. The work was never about demonstrating personal virtuosity. It was about using the medium of rock music as a way of thinking — testing ideas about sound, structure, and audience expectation.

Which explains why Red Krayola’s catalog continues to feel oddly alive. The records are not polished monuments to technical achievement. They are documents of exploration, full of wrong turns, strange detours, and flashes of accidental beauty.

In a culture that often equates artistic success with increasing refinement, Mayo Thompson chose the opposite path. He embraced awkwardness, instability, and deliberate imperfection as creative tools.

And if that occasionally meant playing the guitar badly — well, that too was part of the design.

Badly, perhaps.

But never accidentally.

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In Defense of Conor Oberst

Note: This essay focuses on the songwriting of Conor Oberst and the broader arc of his work as a writer and performer. It does not attempt to settle every critical debate about his career or evaluate the many shifting narratives that have surrounded him over the years.

Instead, the argument here is simpler: when listeners return to the songs themselves — especially pieces like “Cape Canaveral,” “Easy/Lucky/Free,” and “I Didn’t Know What I Was In For” — the caricature of Oberst as merely an overwrought diarist becomes difficult to sustain. Whatever one thinks of the mythology around him, the writing continues to reward careful listening.

For more than twenty years now it has been fashionable to treat Conor Oberst as a kind of permanent adolescent: the patron saint of overwrought confession, the boy genius who mistook emotional intensity for wisdom and simply never grew out of it. Even listeners who admired the early records sometimes adopt a gentle condescension when talking about him now. Those songs were powerful, they say, but they belonged to a particular moment — a moment of youthful melodrama that serious listeners eventually leave behind.

The outline is familiar. Too many feelings. Too many words. Too much trembling urgency in the voice. Somewhere along the way Oberst became shorthand for the idea that emotional sincerity, taken too far, turns embarrassing.

But like many tidy cultural narratives, this one collapses as soon as you start listening carefully again.

The first thing worth remembering is that Oberst began writing and recording music at an age when most people are still learning how to articulate their own thoughts. The early Bright Eyes records captured something very specific: the internal weather of late adolescence and early adulthood. The confusion, the moral absolutism, the sudden swings between despair and hope. Critics often call this melodrama, but melodrama is sometimes just another word for emotional honesty before the world teaches you to disguise it.

What Oberst did during those years was document the process of becoming a person. The songs are full of doubt, self-contradiction, and grand declarations that may not survive contact with reality. But that is exactly how young consciousness works. It moves through extremes. It searches for certainty and then dismantles it. Listening to those records now is less like hearing a performance than like reading a diary written in real time while the author tries to understand himself.

The voice, which so many critics found grating, was central to that effect. Oberst sang as if the words were arriving at the exact moment he needed them. The wavering pitch, the occasional cracks, the sense of someone pushing language slightly faster than it could comfortably travel — all of that created the feeling of urgency. It sounded like a mind thinking out loud.

The strange thing about Oberst’s career is that this intensity became the very thing people later held against him. Emotional transparency, once celebrated as authenticity, gradually hardened into caricature. Listeners who had grown older began to treat the songs as artifacts from a younger self they preferred not to revisit. Oberst did not change enough for some critics, while for others he changed too much.

But the best way to understand his writing is to look closely at several songs that capture the full range of what he does. “Cape Canaveral,” from his 2008 solo record, is often cited by fans as one of his finest achievements, and for good reason. The song moves with a calm, reflective confidence, drifting through memory, regret, and travel before arriving at a quietly devastating insight: “Every time I try to pick up the pieces / Something shatters.” The writing has none of the frantic urgency critics associate with Oberst. Instead it feels mature, patient, almost philosophical — proof that his gift for emotional clarity did not disappear when he left his early twenties.

Another example arrives with “Easy/Lucky/Free,” one of the defining songs from Digital Ash in a Digital Urn. The track looks outward rather than inward, sketching a world where technology and surveillance gradually erode the illusion of personal freedom. The chorus lands with a mixture of dread and irony that feels more prophetic with every passing year. What might once have sounded like youthful paranoia now reads as a remarkably prescient meditation on the digital age.

And then there is “I Didn’t Know What I Was In For,” perhaps the most quietly devastating song of Oberst’s middle period. The track unfolds with almost conversational simplicity, recounting memories of youth, friendship, and the slow arrival of adult responsibility. By the time the final lines arrive — “You said that you hate my suffering / And you understood / And I said that I love you too” — the song has achieved something rare: a portrait of adulthood that feels honest without becoming cynical.

Taken together, these songs reveal the real architecture of Oberst’s songwriting. Beneath the reputation for emotional excess lies a writer deeply concerned with memory, time, and the fragile ways people try to make sense of their lives. His best work captures the moment when experience shifts from confusion into recognition — when a half-formed feeling finally finds the right words.

Another reason Oberst’s work continues to resonate is that he writes from inside experience rather than from a critical distance. Many songwriters polish their observations until the emotional edges disappear. Oberst tends to leave the edges intact. His songs preserve the awkwardness, the uncertainty, the half-formed thoughts that accompany real moments of reflection. The result is sometimes messy, occasionally excessive, but often uncannily recognizable.

This quality also explains why Oberst has remained so influential among younger songwriters. He helped create a space in indie music where vulnerability could coexist with literary ambition. The songs suggested that personal confession and careful craft were not mutually exclusive. For a generation of listeners trying to articulate their own emotional lives, that permission mattered.

None of this means that every Oberst record works equally well, or that every lyric survives scrutiny. A career built on openness will inevitably produce uneven moments. But the larger body of work tells a more interesting story than the caricature of a permanently anguished songwriter. It shows an artist who has spent decades documenting the slow evolution of a restless mind.

And perhaps that is the real reason Oberst continues to provoke such divided reactions. His songs refuse to adopt the protective distance that many listeners eventually develop toward their own past selves. Instead they remain exposed — still searching, still uncertain, still willing to ask questions that adulthood often teaches us to bury under routine.

In that sense the emotional intensity people once dismissed as youthful melodrama begins to look different. It becomes a record of someone refusing to abandon the difficult work of feeling deeply about the world. For listeners willing to meet him there, the songs offer something rare in modern music: the sound of a consciousness continuing to unfold, one uneasy thought at a time.

Note: This is the third piece in our series “In Defense Of.” Iy you enjoyed this essay, you may also enjoy the one on Mark Kozelek. You can access it below.

In Defense of Mark Kozelek