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

Music motherfucking rules

Me

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

Bob Dylan

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

Conor Obrest

Note: This list speaks for itself, it is simply my 20 favorite songs of all time that include lyrics. For this list I have included extended commentary on each song. When I first published this list it was 110 songs long, and I will publish a full 250 this time in several installments. With the first publication, several people let me know that they had discovered new songs from it, and honestly that is the best outcomes I could have hoped for. This list does not include ambient music or jazz, two genres I also love. The list is a product of nearly 40 years of intensive music listening, so it is, at a minimum, highly curated. Thank you for reading, and may you find a new favorite somewhere here.

1. Cape Canaveral — Conor Oberst

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

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

I have loved Cope for about eight years since I first heard it shorty after the release of the record it is on, Conor’s solo self titled debut from 2008. It is in my opinion his most beautiful and moving song. Conor also wrote my number 13 favorite song, Easy/Lucky/Free, which I write about below. Cape Canaveral uses the space program—those televised launches from decades ago, the spectacle of rockets lifting off into the unknown—as a proxy for growing up in America in the latter part of the 20th century. It’s about distance, aspiration, and the strange way in which memory reshapes people and moments over time.

It is one of the most gorgeous American songs ever written. “I watched your face age backwards / changing shape in my memory / you told me victory’s sweet / even deep in the cheap seats.” This is one of the loveliest passages ever set to music. Oberst is doing something subtle and devastating here—he’s taking the language of triumph and reframing it from the margins. Victory’s sweet even deep in the cheap seats is not a grand statement, however it is oddly triumphant. It’s about making meaning over time, with partial access, and moving from watching to participating.

That’s what the whole song feels like: an attempt to construct something lasting out of fragments—TV images, half-remembered conversations, the emotional residue of growing up. The rockets go up, but the song stays grounded in what it felt like to watch them, to want something more without knowing exactly what that “more” was. Full body chills every time. Conor is my number three artist of all time, and Cape Canaveral is exactly why.

2. Leaving LA — Father John Misty 

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

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

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

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

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

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

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

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

Number two. Father John Misty fucking rules.

3. Cruiser — Red House Painters

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

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

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

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

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

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

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

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

Number three. My man.

4 (t). Houses on the Hill

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

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

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

Motherfucking full-body goosebumps. Full-body tears.

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

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

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

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

It simply fucking rules. Stay tuned.

4 (t). It’s Never Been a Fair Fight

5. Tulsa Queen — Emmylou Harris.

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

Then straight into:

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

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

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

I get full body chills and my eyes well up with tears every time I hear Tulsa Queen. Emmylou is the greatest vocalist of all time by far, and Tulsa presents the clearest evidence—not because it’s flashy or showy, but because it is so perfectly, devastatingly controlled. She doesn’t overpower the song; she becomes it. The song starts—“I saw the train/ in the Tulsa night/ calling out my name/ looking for a fight”—and it’s just pure magic. Just unbelievable. The phrasing, the restraint, the sense that the story is already in motion before you’ve even arrived—there is nothing like it. You’re not being introduced to a narrative; you’re being dropped into the middle of one that already feels lived-in and already carries weight.

What makes Tulsa Queen so overwhelming is that it distills everything that makes Emmylou Harris who she is as an artist across her entire career: the fusion of country, folk, and rock sensibilities; the emotional clarity; the ability to inhabit a character without ever losing the self; the sense that every line has been earned. From her earliest work through her later records, she has always been able to locate the emotional center of a song with uncanny precision, but here she doesn’t just locate it—she holds it, perfectly, for the entire duration. It exists in the same emotional universe as something like “Boulder to Birmingham”—another wonderful, better-known masterpiece—but Tulsa Queen goes deeper.

Where “Boulder” is open grief, expansive and communal, Tulsa Queen is interior, private, almost dangerous in how close it lets you get to the narrator’s unrest. It feels less like a performance and more like a confession you were never meant to overhear. There are no words in any language to fully describe the feeling of listening to Tulsa Queen. That’s not hyperbole; it’s recognition. The song operates at a level that bypasses explanation and goes straight to the nervous system. It doesn’t ask to be analyzed—it insists on being felt. Emmylou baby you remain the GOAT.

6. Faded — Afghan Whigs.

The Afghan Whigs’ lead singer Greg Dulli does something remarkable of Faded, which is blend swagger, menace, mystery, bravado, and also deep insecurity in one package. Seeing the Whigs play this as the encore at the Paradiso in Amsterdam in 2017 was one of the highlights of my life. It lands as an encore because it has to—it’s the only place a song like this can go. It doesn’t just end a set; it empties it out. Faded closes Black Love, which is not just an album but a fully realized world—cinematic, shadowy, saturated with urban crime, bad decisions, and the kind of late-night moral drift that never quite resolves.

Across the record, songs like Going to Town and Honky’s Ladder are all forward motion and attitude, pure swagger on the surface. But that swagger always feels a little overextended, like it’s covering something fragile underneath. By the time you get to Faded, the cover is gone. What’s been hinted at all along—doubt, damage, a kind of spiritual exhaustion—comes fully into view. There is no mystery as to why this has been the encore for every Whigs show for 30 years.

When Dulli asks to be lifted out of the night, to have someone look down and see the mess he’s in, it doesn’t feel performative. It feels exposed. The bravado is still there, but it’s cracked open, and what comes through is something far more human and far more dangerous. Not only is this the best Afghan Whigs song, Black Love is their best album by a mile. Everything they do well converges there—the mood, the storytelling, the tension between control and collapse—and Faded is the final, perfect release of that tension. He is a genius and the motherfucking man, and Faded is the best of many great Whigs songs. A worthy inclusion at number seven.

7. My Life Is Sweet — Simon Joyner.

“Met the drinker for a drink/ back when I was drinking everything but the kitchen sink”—and sure enough this song is about drinking, and drunks. Joyner’s friend is an alcoholic, and at the time of writing so is Joyner. They go to a bar and sit together, talking a little, mostly not, letting the night pass in that particular way that only two people who know each other well can manage.

Ultimately, this song is about male companionship, and how a quiet drink with a quiet friend can be life-saving when you really need it. Joyner takes a taxi home—drunk, or hungover, or somewhere in between—and collapses on the floor. And then the song ends with that extraordinary sequence where the city drops away, becomes something almost beautiful from a distance, and he arrives at that fragile, hard-won conclusion: my life is sweet. Anyone who is, or has been, a drinker will immediately recognize what Joyner is doing here—he is rationalizing the unrationalizable, but at the same time he’s not lying about it.

Is drinking so, so sweet? Yes and no, of course—and that tension is the point of this truly magnificent song. Part of what makes Joyner so compelling is how deeply rooted he is in the Omaha scene that would later produce Conor Oberst. Joyner is the elder figure there—born in 1971, a few years ahead of Oberst, who came up in the early ’80s generation—and his influence on Conor is both documented and unmistakable. Oberst has cited Joyner as a major influence, and you can hear it: the diaristic honesty, the willingness to let a song feel unfinished, the comfort with contradiction.

Joyner was mapping that terrain before it had a name, and before it had an audience beyond the local. He’s also massively underrated. He has other great songs—Fearful ManOne for the Catholic Girls—but My Life Is Sweet feels like the purest distillation of what he does best. There’s no artifice, no attempt to resolve the contradictions he’s living inside. Just a voice, a night, a friend, and the uneasy grace of getting through it. Anyone who’s been there knows: that’s more than enough.

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

Tommy Stinson, the bassist from The Replacements—went on to have, in my opinion, an even better solo career than the band’s lead singer Paul Westerberg. And considering that Westerberg is a genius and an absolute legend, this is saying something.

Stinson was barely out of childhood when the Replacements were at their peak—a teenager holding down the low end in one of the most chaotic, brilliant bands of their era. That early immersion shows up everywhere in his later work: the instinct for melody, the looseness, the sense that a song should feel lived-in rather than perfected. But what’s striking about his post-Replacements career—through Bash & Pop and his solo records—is how much he refines that instinct. The pure thrash and glorious sloppiness of early Replacements material gives way to something sweeter, more polished, but never sanitized. The edges are still there; they’re just better framed.

Never Aim to Please comes from Bash & Pop’s first record, Friday Night Is Killing Me, and Stinson has alternated between Bash & Pop releases and solo records over the 35 years since the Replacements broke up. In the first verse, Stinson sings about the absence of a point of view, and that marvelous line always reminds me of Westerberg’s writing on “Someone Take the Wheel”—that same sense of dislocation, of trying to find footing in a world that keeps shifting under you. There’s a great anecdote from Westerberg that early on, the Replacements pretended to hate The Rolling Stones—it was part of the pose, the punk posture. But it was just that: a pose. They actually loved the Stones.

And you can hear that lineage clearly in Stinson’s work. For all of his originality, he’s very much working in that classic rock tradition—songcraft, groove, emotional directness—but he does it in the best possible way, without nostalgia or mimicry. It feels inherited, not borrowed. Stinson may not claim to have a point of view in this song, but he’s been a remarkable curator and keeper of the Replacements’ legacy, especially as Westerberg has retreated from the music scene over the last decade. There’s a quiet authority in that, a sense of continuity that runs through his work. And the song itself? It just fucking kicks. It hits me in all the feels every time, and it is a worthy number nine.

9. A Bathtub in the Kitchen — Craig Finn.

My favorite of many possible Finn contendersBathtub is about friendship, guilt, redemption, betrayal, and mostly about thankfulness. It’s the greatest song ever written about New York City and also about moving to a big city in general. Finn compresses an entire early chapter of a life into a few lines—the arrival, the uncertainty, the desperation to be claimed by the city, and the friend who makes that possible by opening his door. That friend—Francis—is the emotional center of the song. Twenty years earlier, he’s the one who shows the narrator the ropes, lets him crash on the couch, gives him a foothold when he doesn’t have one. He is, in a very real sense, the reason the narrator makes it at all. And now, in the present of the song, Francis is down and out, struggling, a diminished version of the figure who once seemed stable and generous.

What makes the song hit so hard is the narrator’s response to that reversal. There’s hesitation, even avoidance. He tries, briefly, to pass the responsibility off—to suggest that someone else, someone more put-together, might be in a better position to help. It’s a small moment, almost throwaway, but it reveals everything: the discomfort, the guilt, the instinct to deflect when confronted with a debt that can’t really be repaid. Because that’s the truth the song circles around—some debts can’t be repaid. Not cleanly, not proportionally.

In the end, the narrator does give Francis money—two hundred bucks—but it lands with a kind of quiet insufficiency. It’s something, but it’s not enough, and it never could be. You can’t square that kind of ledger. You can only acknowledge it. And that’s where the thankfulness comes in. Not as a resolution, not as a way of tying things up neatly, but as a recognition that what was given mattered, even if what is returned will always fall short. Finn doesn’t offer redemption in the traditional sense. He offers something more honest: awareness, discomfort, and the attempt—however partial—to do right by someone who once did right by you. It’s a stunning, stunning song and an absolutely worthy number nine.

10. Dreadful — The Violet Burning

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

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

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

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

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

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

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

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

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

Two minutes and twenty-eight seconds. Nothing wasted.

Number ten.

This bad boy fucking slaps.

11. The Traitor — Leonard Cohen

Cohen’s early career began not as a songwriter but as a poet and novelist—already established in literary circles before he ever stepped into popular music. When he moved into song, it wasn’t a reinvention so much as a translation. Early breakthroughs like Suzanne and later Bird on the Wire introduced a voice that felt unlike anything in contemporary pop: formally literary, emotionally restrained, but spiritually enormous.

Across a career that stretches from that early poetic minimalism to late-period gravity, Cohen repeatedly returned to the same emotional territory in different registers. Seems So Long Ago, Nancy carries quiet tragedy without spectacle. Death of a Ladies’ Man leans into chaos and contradiction. Alexandra Leaving and That Don’t Make It Junk show a late-career clarity—less ornament, more acceptance. And then, right at the end, The Night of Santiago from Thank You for the Dance—completed after his death by his son Adam—feels like a final echo rather than a conclusion, as if the voice is still resolving even after it has stopped.

But it is this passage that sits at the center of everything: “I told my mother, mother I must leave you / preserve my room and do not shed a tear / should rumor of a shabby ending reach you / it was half my fault and half the atmosphere.” Quite possibly the greatest verse ever set to paper.

There is something almost unbearable in its tenderness—the attempt to leave without destroying what you came from, to depart without turning departure into permanent damage. “Preserve my room” is not a realistic request; it is a desire for time to stop, for memory to remain untouched while the self moves forward into uncertainty, drift, and likely failure.

Cohen does something very few writers ever manage: he distributes responsibility without dissolving it. “Half my fault and half the atmosphere” is not an excuse—it is an ethics of existence. The self is accountable, but so is the world that formed it. There is guilt here, but no self-pity. There is clarity, but no absolution. He is naming the condition of being human with a precision that feels almost too large to hold. And what makes the song extraordinary is that it refuses resolution. Cohen never tries to solve the tension he has introduced. Instead, he inhabits it fully.

Across his work—from the early poetic breakthrough to the late songs of acceptance and erosion—he speaks to the quester, the striver, the poet, and the mystic in each of us. Not by offering answers, but by dignifying the act of searching itself. Leaving, longing, failing, seeking—these are not problems to resolve, but conditions to endure with awareness. His voice carries all of it: resignation, yearning, and a kind of quiet, unbreakable grace.

His best by a mile. Simply marvelous.

12. Gorgeous (live)— The Violet Burning

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

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

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

Motherfucker.

Of course.

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

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

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

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

And Michael Pritzl makes me believe him every goddamn time.

13. Albuquerque Mark Kozelek (Neil Young Cover)

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

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

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

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

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

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

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

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

Probably other periods too.

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

Motherfucker.

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

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

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

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

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

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

14. Oh My Sweet Carolina — Ryan Adams

One of the most beautiful and sad songs in modern American songwriting. The record Heartbreaker—Adams’ solo debut after his run fronting Whiskeytown—remains his peak for many listeners. It’s also the album where everything still feels unforced: the writing, the pacing, the emotional exposure. Later records like Gold brought wider recognition, and something like Chris gets close in flashes, but Heartbreaker has a coherence of mood that he never quite replicated.

What defines Oh My Sweet Carolina is its dual perspective. On the surface, it’s a travel song—young man on the road, drifting through cities like Cleveland, accumulating damage, spending energy and money with a kind of reckless momentum that feels both chosen and inevitable. But underneath that motion is something much older: a pull backward, toward origin, toward a place that isn’t just geographic but emotional. North Carolina isn’t just home—it’s coherence.

The Cleveland passages (“So I went on to Cleveland and I ended up insane/ I bought a borrowed suit and learned to dance/ And I was spending money like the way it likes to rain/ Man, I ended up with pockets full of cane”) carry that classic Ryan Adams contradiction: charm and collapse in the same breath. The narrator moves through instability with the confidence of someone still convinced that motion equals meaning, even as that belief is starting to fail him. It’s the sound of someone learning, mid-stream, that movement alone doesn’t resolve anything. And then the emotional center of the song reveals itself: (Oh mw sweet Carolina/ what compels me to go/ oh, my sweet disposition/ may you one day carry me home), the longing not just to return, but to be returned in one piece. Not improved, not transformed—just intact.

This is where the collaboration with Emmylou Harris matters. Her voice doesn’t decorate the song; it stabilizes it. It sounds like witness. Adams has written other songs that brush this same emotional territory—English Girls ApproximatelyOh My God, Whatever, Etc.Still a CageBirmingham—but none of them quite hold the same balance of youth and exhaustion, romance and reckoning. Oh My Sweet Carolina feels like a hinge between those states: a young man already speaking like he understands what the older version of himself will miss. It’s a debut record moment that feels strangely final. A song about going forward that only makes sense when you understand what it costs to leave things behind. A truly majestic entry—and a worthy entry here at fifteen.

15. (T) Montreal Rock Band Somewhere — Happyness

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

They suck.

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

So yeah, I don’t like Arcade Fire.

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

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

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

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

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

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

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

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

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

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

15. (T) Crushed Out — Bad Moves

17. Caribbean Wind — Bob Dylan

18. (T) Center of Asia — Paul Pena 

19. (T) Rocket and a Bomb — Michael Knott

This is Knott’s best-known—and, for many people, only known—song. It’s the one that traveled beyond the small, fractured world he spent his career navigating, the one that people who don’t know the rest of his catalog can still recognize. And that’s fitting, because it captures almost everything that made him singular. Knott never fit comfortably inside the Christian rock community that was supposed to be his home. He clashed with labels, bounced from one situation to another, tried repeatedly to start his own imprints just to maintain control of his work, and spent much of his career existing in the margins of an already marginal scene. There were too many expectations, too many rules about what a “Christian artist” was supposed to sound like, what he was supposed to say, how cleanly he was supposed to resolve things. Knott refused all of it.

You can hear the lineage—artists like Larry Norman laid some of the groundwork—but Knott is no inheritor in the traditional sense. He’s a total original. Where Norman and others often leaned toward proclamation, Knott leaned into contradiction, mess, unresolved tension. He wasn’t interested in presenting faith as an answer; he was interested in showing what it felt like to live inside it when the answers didn’t come.

His career reflects that restlessness. From the early chaos of Popsicle and Popsavers, through the darker, more aggressive phases of L.S. Underground and LSU, into his solo work and projects like Aunt Betty’s, Knott kept shifting forms, refusing to settle into anything that could be easily categorized. The sound changed, the bands changed, the labels changed—but the core impulse didn’t: tell the truth as he experienced it, even if it didn’t line up with what anyone wanted to hear. Rocket and a Bomb distills all of that into something deceptively simple. There’s humor in it, almost absurdity—“Mr. God, is there a Ms. God? Can she help me find a job?”—but it lands because it’s so nakedly real. This is a man of Christ who is also a man of the world, standing in the gap between those identities, not reconciling them but living them both at once. He’s not asking for salvation in the abstract; he’s asking for something immediate, practical, human. He just needs a goddam job.

That tension runs through everything he ever said and did. His line—“I know Christ. It doesn’t make me good; it doesn’t make me bad; it doesn’t make me anything. It just means I know Christ.”—might be the clearest articulation of his entire ethos. Faith is not a moral upgrade, not a solution, not a transformation you can point to and quantify. It’s a relationship, and relationships are messy. So what is a rocket and a bomb? They’re things most people don’t get to touch. Power, transcendence, impact—forces that exist beyond the everyday. The narrator wants a job, something stable, something achievable. But he also wants more. He wants access to something larger, something explosive, something that breaks the limits of an ordinary life. Knott lived that contradiction. He lived fast, pushed hard, refused to smooth out the edges that made him difficult to categorize or contain. He burned through systems that couldn’t hold him, left behind a body of work that feels both deeply personal and strangely universal. He had to.

20. There Must Be More Than Blood — Car Seat Headrest.

This is a tricky one, because it forces us to deal with a shift—not just in a song, but in an artist. My thesis is that this is Will Toledo going into a kind of relative hiding, and the song reads like a document of that transition in real time. His early work—from Beach Life-in-Death through Nervous Young Man to Sleeping with Strangers—was as direct, as exposed, as heart-on-the-sleeve as anything in the last decade of rock music. He wasn’t just confessional; he was incapable of not being confessional. He was the heart on his sleeve songwriter of his generation. You didn’t have to work to understand him—you just had to be willing to feel what he was feeling.

And then you put that next to someone like John Darnielle—super prolific, deeply lofi in his early approach, but always a little more mediated, a little more constructed. Darnielle throws his material against the wall and lets it accumulate into narrative. Toledo, at his best, just bleeds. So when Making a Door Less Open arrives, even the title signals a shift. Something is closing. Something is being sealed off. The masks—first the normal face coverings, then the Trait mask, then the gas mask—aren’t just stagecraft. They’re statements. The question isn’t “what is he hiding?” but “why does he suddenly feel the need to hide at all?” There Must Be More Than Blood sits right in the middle of that tension. You get these images of dislocation—of a life that used to feel rooted and now doesn’t. The delta, the shoreline, the houses stripped away—it doesn’t read like a literal disaster so much as an internal one. The sense of ground disappearing. Of structures—family, identity, whatever “home” used to mean—losing their coherence. He talks about wasting time, but you know that’s not true. He’s one of the most prolific songwriters around. What he’s really describing is a shift in how that time feels from the inside.

And then there’s the second movement—the red-eye flight, the self-recognition that barely qualifies as recognition at all. He sees himself, but only as an outline, a set of lines without substance. That’s the real break from the early work. The old Toledo was hyper-present, almost overwhelmingly so. This Toledo is thinning out, becoming harder even for himself to locate. So what do you do when you can’t see yourself clearly anymore? You disappear further. You become, in a sense, the Invisible Man. That’s what the masks start to feel like—not affectation, but adaptation. A way of dealing with a self that no longer feels stable enough to present directly. And if you follow that thread forward, you get to The Scholars—The Scholars—his most recent record. It’s even more oblique than Door. There are great songs there—Stay With Me (I Don’t Want to Be Alone)Equals—but they’re harder to parse, less immediately accessible. The emotional core is still there, but it’s buried deeper, refracted through more layers.

Part of that may simply be life catching up with him. Toledo dealt with serious health issues in the lead-up to that record—long COVID, histamine intolerance—and the process became more collaborative, less singularly driven. That alone changes the texture of the work. The lone voice becomes one voice among several. The signal diffuses.So There Must Be More Than Blood starts to feel like a hinge point. The moment where the old mode—pure exposure, pure immediacy—begins to give way to something more guarded, more fragmented, more difficult to access. But the core hasn’t disappeared. It’s just harder to reach. And that’s why the song matters. It captures an artist in the act of losing something essential—or at least transforming it into something less direct, less available, maybe even less comforting. Will Toledo is a mysterious guy. Deep, fragile, a little haunted, clearly carrying more than he lets on. He’s dealt with some tough stuff, and you can feel it in the way the work shifts over time. And for anyone still saying “rock is dead”—they can fuck off. There is still The Hold Steady and Car Seat Headrest making records that matter, records that wrestle with something real. You just have to be willing to meet them where they are now, not where they used to be.

On Conor Oberst’s “Cape Canaveral”: The Greatest Song of All Time

Note:

I have been working for several months on pretty challenging project: ranking my top 250 favorite songs of all time. Yeah I know. It’s a lot.

There are now nearly 500 songs under consideration for what I continue, somewhat inaccurately, to call my Top 250. Songs rise. Songs fall. Songs appear from nowhere and kick the living shit out of songs I have loved for thirty years.

And then something genuinely unexpected happened.

For the past decade of more, Emmylou Harris’s “Tulsa Queen” has been my favorite song of all time. I assumed it probably always would be.

I was wrong,

The new number one is Conor Oberst’s “Cape Canaveral.”

This essay is partly about that song and partly about the forty-plus years of listening that somehow brought me to it: childhood folk records, American musical history, Emmylou Harris, Bob Dylan, Craig Finn, Bright Eyes, Better Oblivion Community Center, Ryan Adams, live music, and the strange experience of discovering that a song you have known for years has suddenly become something else entirely.

Music rules, everybody.

Long live music.

Epigraphs:

Music rules
—Evervbody

I support the French Revolution
—Dean Wareham

I heard that victory’s sweet/ even deep in the cheap seats
—Conor Oberst

Introduction:

For the last several months on the Kyoto Kibbitzer, I’ve been working on a piece entitled “The Top 250 Songs of All Time.” This is, of course my list, and it is therefore entirely subjective. Nevertheless, it is the product of more than forty years of intensive, daily listening to music of all kinds.

“Cape Canaveral,” by Conor Oberst, recently displaced “Tulsa Queen” as my number-one song of all time.

This is no small thing. “Tulsa Queen” has been my favorite song for at least ten years, possibly longer. The first full album of hers that I fell in love with was the 2008 live record Spyboy. I knew of Emmylou before that, of course, and I especially liked “’Til I Gain Control Again,” which at that point I knew largely through the immaculate This Mortal Coil cover. I was also familiar with her connection to Gram Parsons, and knew how devastated she had been by his death. I knew songs like “Boulder to Birmingham,” and I may or may not have heard “Tulsa Queen” a time or two. I don’r know. It was all a long time ago.

In any case, it was Spyboy that really made me pay attention to Emmylou for the first time. I devoured the record and loved it. I still do.

Listening For Something

By the time I heard Spyboy, I had already listened intensively to hundreds and hundreds—probably thousands—of records. In fact, my relationship with music goes much farther back than that.

When I was six or seven, Joan Baez’s “The Sweet Sunny South” was the first song I truly fell in love with. It simply captivated me. About a year earlier, I had dug an old record of American folk songs out of what we called the “back closet,” which was actually the front closet. I forget the title. It was something straightforward, along the lines of The Greatest American Folk Songs.

The song I really fell in love with was “The Big Rock Candy Mountain.” This song contains the great verse:

In the Big Rock Candy Mountains
You never change your socks,
And the little streams of alcohol
Come a-trickling down the rocks

I understood the song, even then, to be a fantasy of escape: the mythical paradise of the hobo, where ordinary deprivation and misery have somehow been turned upside down.

American musical history fascinates me. In the mid-twentieth century, collectors such as Alan Lomax preserved thousands upon thousands of American folk performances that might otherwise have disappeared. Those archives remain an invaluable resource for musicians, critics, historians, and ordinary music fans alike.

I’ve poked around in archives like Lomax’s myself, and I find them endlessly fascinating. My primary musical preference remains American and British folk and Americana. I also love most forms of country music, although, to be honest, some popular country gets a little too saccharine and sappy for me.

I also love indie and alternative rock, especially the indie music of the 1990s and early aughts. As I’ve written elsewhere, I don’t keep up with new music these days as much as I probably should. I do try to keep up with new releases from favorite active artists: Conor Oberst, Craig Finn, Sun Kil Moon, Ryan Adams, Neil Young, and even Bob Dylan, who remarkably continues making music well into old age.

And this brings me back to “Cape Canaveral.”

When I finally fully appreciated the song, I realized something strange:

I had been listening for it my entire life.

Cape Canaveral

For my money, “Cape Canaveral” is primarily a song about escape.

It is also a song about the vicissitudes of patriotism, about being an American, about the Fourth of July, and the American space program. It is one of the sweetest songs I have ever heard. It is also super sad. Conor just has a way of breaking a guy’s heart.

There is one particular acoustic live performance on KCRW in 2014 that I particularly love. Conor introduces the song by talking casually to the audience about his big backyard in Omaha, being outside at night, looking up at the stars, and relaxing with whoever happens to be beside you. Then the first few notes hit, and the effect is devastating.

I love music. I love live music the most. I also love musicians introducing their songs. I’ve written about this at some length elsewhere. These little introductions can become almost as important to me as the songs themselves. They cement a song in a place and a moment. They also give you a little insight into the artistic process, which I find super cool.

And then the song starts.

What gets me first is the sound. “Cape Canaveral” is remarkably spare. Conor doesn’t overplay things. The acoustic guitar carries the song along gently, and his voice sounds simultaneously intimate and far away. The whole thing has the quality of somebody sitting outside late at night, thinking about his life while everyone else has gone to bed.

And then there are the images: rockets, orange groves, interstate highways, television, war movies, stars, cheap seats. The song keeps moving between the enormous and the ordinary: outer space and somebody’s backyard; American history and private memory; the grand technological dream of the space program and one lonely human being trying to understand where he is.

That scale is part of what makes the song so beautiful to me. The rocket goes up. The stars get smaller. Everything changes.

And then there is the line that just breaks my heart every time:

Victory’s sweet
Even deep in the cheap seats

FUCK YEAH CONOR. You know it, baby.

And underneath all of this, I hear escape.

That is the thread that connects “Cape Canaveral” to “The Big Rock Candy Mountain” for me. One song imagines a hobo’s paradise and the other looks toward rockets, highways, and the night sky, but both contain the same ancient human impulse: maybe there is somewhere else to go.

Maybe there is some kind of life beyond this one. Maybe if you keep moving long enough, something will finally open up for ya.

For now, anyway, “Cape Canaveral” is my favorite song of all time.

Is Conor Obrest My Favorite Songwriter?

As I write this today, when I really think about it, Conor Oberst may be my favorite songwriter of all time.

Actually, I have three favorite songwriters and a close fourth. My three are Conor Oberst, my current favorite; Bob Dylan, the historical champion; and Craig Finn.

Until very recently, I would have sworn to you that Finn was—and probably always would remain—my favorite songwriter. But it has now been a few weeks since I replaced “Tulsa Queen” with “Cape Canaveral,” and during that time I have probably listened to “Cape Canaveral” eighty or a hundred times. Sometimes I listen on Spotify. More often, I return to the live performance.

Conor first burst onto the scene as a teenage wunderkind with Bright Eyes. I like Bright Eyes a lot. I especially love “Easy/Lucky/Free” and “Gold Mine Gutted,” both from 2008’s Digital Ash in a Digital Urn. This is a curious and funny title, and I like it.

A lot of people also know I’m Wide Awake, It’s Morning. I like that record too, but it has never really floated my boat.

When it comes to Conor’s solo catalog, however—and then Better Oblivion Community Center, his collaboration with Phoebe Bridgers—the picture starts to shift.

In addition to “Cape Canaveral,” I love “Classic Cars,” and “A Little Uncanny,” which is totally out of control. I love “Next of Kin,” including this wonderfully deadpan line:

Yeah I met Lou Reed and Patty Smith
I didn’t make me feel different.

I liked these lines so much that I used them as an epigraph to an earlier piece.

I love “No One Changes,” one of Conor’s saddest songs. I love “I Don’t Want to Die (In the Hospital),” which is also extremely funny. I love “The Rockaways.” I love so many of his songs.

And then there is Better Oblivion Community Center.

When I first hear the record, the immediate standout was “Dylan Thomas.” I wrote about it almost immediately in an essay called “On the Song Dylan Thomas and Rhyme.”

I wrote that piece very fast—in ten or twelve minutes, as I recall—while standing on a train from Akasaka Station to Tokyo Station.

I’m proud of the piece. Quite improbably, it has also experienced a dramatic resurgence in readers recently.

I find all this very exciting. It makes me proud to be a writer and proud to have kept a near-daily blog for all these years. I love writing. I love reading. I love everything about them, and I always have.

There are many other great Conor and Bright Eyes songs I could name, but the list would tale up too much space. Suffice it to say that today I believe Conor Oberst and Craig Finn are the two greatest songwriters working, while Dylan remains the historical champion.

Ryan Adams

If Conor is my current favorite, Finn is tied or running a very close second, and Dylan remains the historical champion, I would be remiss not to mention Ryan Adams in the four spot.

There is one ugly episode in Conor’s history worth addressing first. In 2013, a woman publicly accused Oberst of raping her after a Bright Eyes concert years earlier. Oberst denied it. The woman subsequently retracted the accusation entirely apologized, and admitted that she had fabricated it.

Making a knowingly false accusation of rape is an appalling thing to do. It harms the falsely accused person, and it also makes life harder for actual victims of sexual violence. Rape is an atrocious crime. Deliberately inventing one is a different act with different consequences, and there is no reason for me to construct some kind of grand hierarchy here. The relevant point is simpler: the allegation against Oberst was withdrawn by the person who made it, who acknowledged that she had fabricated it.

Ryan Adams presents a messier case.

In 2019, multiple women, including his former wife Mandy Moore and Phoebe Bridgers, a then up and coming musician who toured with Ryan around this time, publicly accused Adams of manipulative or abusive behavior. Moore described psychologically controlling behavior, and said that Adams had not sufficiently helped to advance her music career. Specifically, she accused Adams of not giving her free studio time. At the time and still today, I find this accusation completely ridiculous. It is his studio. He can with it whatver he wants.

Bridgers, in turn, described a romantic and professional relationship that she said had became emotionally abusive. She finished the tour with Adams, and the two went their separate ways. Another accusation was more serious. Adams disputed significant portions of the reporting. As of this writing, Adams has never been arrested or charged for any of these incidents.

Whatever judgment one makes about Ryan Adams the man, none of this changes his greatness as a songwriter.

“Oh My Sweet Carolina,” “Damn, Sam (I Love a Woman That Rains),” and “Come Pick Me Up” are indelibly etched into the American folk-rock canon. Mandy Moore has had an successful career of her own, but she and Adams occupy very different musical territories, and comparing their importance as songwriters isn’t particularly helpful.

There is also a curious connection here. Bridgers later formed Better Oblivion Community Center with Conor Oberst, an older man like Adama. I have no idea whether Conor and Phoebe were ever lovers, however it is fun to ship them. I kind of hope they got together once or twice in the studio or at the hotel or something.

I’ll never know. And it’s none of my business.

Ryan therefore stays in the four spot: a difficult man by numerous accounts, a songwriter whose work has meant an enormous amount to me, and another tributary feeding the musical river that eventually brought me to “Cape Canaveral.”

The biography matters. The allegations matter. But this is an essay about listening.

And his songs are why Ryan Adams is here.

A New Number One

So that’s about it. I have a new favorite song, and it’s “Cape Canaveral.”

I don’t foresee it getting knocked out of the number-one spot anytime soon. Of course, I thought the same thing about “Tulsa Queen.”

And I was wrong.

Right now, “Leaving LA,” the glorious song by Father John Misty, is number two. “Cruiser” is number three. The totally slapping “Dreadful,” by The Violet Burning, is number four. And “Tulsa Queen” has now been bumped all the way down to number five.

Sorry, baby. You know I love you.

I continue to listen to music every day, often for several hours. I sleep to music. I wake up to music. I shower and brush my teeth to music. I read to music. I eat to music. I drink coffee and tea to music. I make love to music.

I love music more than almost anything in my life, except my son, of course. I love nearly every form of music, and I love live music most of all. The thrill of a great live concert is unequaled by almost any other experience under the sun.

I did get the chance to see Conor live in Osaka just a few months ago with my friend Jack. It was a small venue downtown. Conor was great. He opened with a few songs I knew and a few I had never heard before.

Although I was having a good time, unfortunately I was so zonked that I had to leave after only about twenty-five minutes. I was disappointed, but I was so tired that I simply had no choice.

Jack told me on the phone the next day that he had left only about five minutes after I did. I guess he too was beyond all help.

That night, anyway, we were completely out of control.

Long Live Music

Part of me wants “Cape Canaveral” to hold onto the number-one spot forever.

Another part of me hopes a new challenger emerges.

“Leaving LA” and “Cruiser” are the obvious contenders, with “Dreadful” right there too. “Tulsa Queen” has already fallen four places, so I don’t see her charging back to number one anytime soon.

But who knows?

The artists I listen to most frequently these days include Whiskeytown and The Jesus and Mary Chain. Both absolutely slap and totally rule. Whiskeytown occupies the folk/country side of my canon; The Jesus and Mary Chain occupy the alternative and early-indie side.

Other artists I play constantly include Craig Finn, Happiness, Daddy Issues, The Violet Burning, and Michael Knott, and many others.

R.I.P. Michael Knott. R.I.P. to a legend.

I listen to so many songs every day that I can hardly keep count. That is one reason I’ve taken to making these lists in the first place. The rankings change. The artists change. I change. Some song I’ve heard fifty times suddenly opens itself up on the fifty-first listen and becomes an entirely different thing.

That is part of the fun. That is part of the mystery. That is why I keep listening.

Long live music. Long live live music. Long live music fans.

Long live Conor Oberst. And long live “Cape Canaveral.”

Amen.


Dedication:

For musicians and music fans everywhere. I love you. And for Conor Oberst. You’re the fucking man, baby.

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.

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 Ryan Adams

Note: This essay is not an attempt to defend Ryan Adams the person. It’s an attempt to defend the continued seriousness of the music. The distinction matters, even if our cultural conversations sometimes pretend it doesn’t. Also, I fucking love Ryan Adams. He is the motherfucking man.

Epigraph:

“When the stars go blue.”
— Ryan Adams

For several years now it has been socially safer to treat Ryan Adams as a closed case: talented songwriter, personal flaws, cultural exile. The outline is familiar enough that most people no longer bother to revisit the work itself. But the strange thing about Adams is that the songs refuse to cooperate with the narrative. They remain stubbornly alive — hundreds of them scattered across albums, demos, and late-night recordings — carrying the same bruised intelligence that first made people pay attention twenty-five years ago. At some point the question stops being whether Ryan Adams is an admirable person. The real question becomes harder and less comfortable: what do we do with an artist whose flaws are obvious but whose music continues to tell the truth in ways very few writers can manage?

Part of the problem is that Ryan Adams belongs to an older model of songwriting — the kind where the emotional life of the artist is inseparable from the work. The songs are confessional without being literal, personal without being autobiographical in any simple way. From the early Whiskeytown albums, to his solo debut Heartbreaker, on to today, Adams has always written like someone sitting in the wreckage of his own choices and trying to understand what just happened. That voice — raw, impulsive, often heartbroken, sometimes self-pitying, often painfully perceptive — was never tidy. It wasn’t supposed to be. The appeal of Adams at his best has always been that the songs arrive before the moral cleanup crew.

When the accusations against him surfaced in 2019, the cultural machinery moved quickly. Adams’s shows were cancelled for a while, he was dropped from projects, and reclassified overnight as an artist whose work had become morally contaminated. Some listeners stopped listening immediately. Others quietly kept listening but stopped talking about it in public. The silence that followed was oddly complete. In a culture that usually thrives on argument, the Ryan Adams conversation simply evaporated.

That disappearance is revealing. It suggests that many people were less interested in wrestling with the complexity of the situation than in resolving it as quickly as possible. Once the story had a clear villain, the cultural instinct was to move on.

But the songs remain.

Listen again to Come Pick Me Up, and you hear a man cataloguing his own emotional incompetence with surgical clarity. Oh My Sweet Carolina still carries that strange mixture of homesickness and resignation that only a handful of songwriters ever capture. Later work — Ashes & FirePrisoner, Chris, the better moments of the sprawling archive that followed — continues the same project: the slow documentation of a person trying, often unsuccessfully, to live with himself.

None of this absolves Adams of anything. It doesn’t erase the accounts of people who describe him as manipulative, volatile, or worse. If anything, the songs themselves suggest that those accounts are not entirely surprising. Adams has been writing about his own volatility for decades. The records are full of it — jealousy, insecurity, emotional chaos, the constant sense of someone struggling to regulate the intensity of his own personality.

What the songs also reveal, though, is a rare level of self-awareness about his own condition. Adams’ best work doesn’t present him as a romantic hero. It presents him as part of the problem.

And that distinction matters.

One of the stranger habits of contemporary cultural criticism is the belief that the value of a work of art should track the moral cleanliness of the person who made it. This is a comforting idea, but it collapses under the slightest historical pressure. Much of the art people still revere emerged from personalities that were messy, selfish, unstable, or worse. Songwriters, perhaps more than most artists, tend to write directly from the fault lines of their own lives.

If we demanded perfect character from every songwriter whose music we admire, the history of popular music would shrink dramatically.

The more interesting question is not whether Ryan Adams deserves redemption. That is not something critics or listeners are qualified to grant. The question is whether the songs themselves still carry meaning once the mythology surrounding the artist has been stripped away.

In Adams’ case, the answer seems to be yes.

The songs are still precise. The emotional details still land. Lines that once felt like romantic exaggeration now sound more like documentation — the sound of a man who understands, perhaps too late, the patterns that keep repeating in his life.

There is something oddly honest about that.

The best Ryan Adams songs have always sounded like dispatches from someone who knows he is partly responsible for the wreckage he is describing. They are not pleas for sympathy so much as attempts at recognition — moments where the singer steps outside himself long enough to see the pattern clearly.

That is why the music persists even when the cultural narrative surrounding it has hardened.

The songs were never about innocence. They were about self-knowledge.

And self-knowledge, even when it comes from flawed people, is still one of the things art is uniquely good at revealing.


Dedication

For Ryan, one of the five greatest songwriters ever and the motherfucking man. I love you baby.

Note: If you like this essay, you may like these others in the same “In Defense Of” series.

On Kris Kristofferson’s “To Beat the Devil”

This piece takes a look at Kris Kristofferson’s “To Beat the Devil.” The song appears on Kristofferson’s self-titled debut album from 1970 on Monument, which is, by any standard, an astonishingly good record. The album features “Me and Bobby McGee,” “Sunday Morning Coming Down,” and “Just the Other Side of Nowhere,” along with the ol’ Devil. That’s four absolute classics right there for ya.

Sunday Morning features an opening quatrain that most other songwriters would trade their career for:

Well I woke up Sunday morning/ with no way to hold my head that didn’t hurt/ and the beer I had for breakfast wasn’t bad/ so I had one more for dessert

(I could play this game all day—Jason Isbell’s Southeastern features another couple life-work worthy couplets:

The first two lines of “Super 8”:

Don’t wanna die in a super 8 motel/ just because somebody’s evening didn’t go so well

And from “Different Days”:

Time went by and I left and I left again/ Jesus loves a sinner but the highway loves a sin.

If I’d written lines that great I’d call it a career and sip martinis on the house for the duration.)

Sunday Morning and Bobby are probably objectively better songs than To Beat the Devil, yet what I like about this one is that Kristofferson states very clearly a kind of founding intention for his life in song and art, right out of the gate. The only parallel I can think of is Craig Finn’s The Hold Steady, whose first album Almost Killed Me kicks off with “A Positive Jam.”

(Here’s Finn telling it like it is:

I got bored when I didn’t have a band/ so I started a band/ we’re gonna start it with a positive jam/ hold steady.

Rock on Craig baby.)

Anyway, let’s get to the focus of this piece. Kristofferson opens with a spoken intro.:

A couple of years back I come across a great and wasted friend of mine in the hallway of a recording studio. And while he was reciting some poetry to me that he had written, I saw that he was about a step away from dying, and I couldn’t help but wonder why. And the lines of this song occurred to me.

Here the singer is looking up at his idol who is both “great and wasted.” I wasn’t around quite yet in 1970, yet I can easily imagine Ginsberg’s “best minds” line hanging over talented folks across a lot of zones. Klosterman wasn’t quite there either (June 5, 1972–a mid Gemini of course), but he was close, and to indulge not for the last time in a little Klostermania, the zeitgeist seemed to be making people thirsty.

The singer receives some scraps of poetry, shards of shattered inspiration, and a song “occurs” to him. He doesn’t state it directly, however we imagine the song arrives fully formed, like “Pancho and Lefty,” or “Kubla Khan.” Thus, To Beat the Devil is also both an answer and an offer of redemption to his idol, who here is John(ny) Cash.

I’m happy to say he’s no longer wasted, and he’s got him a good woman. And I’d like to dedicate this to John and June, who helped showed me how to beat the devil.

The singer takes up the mantle of the master, and in so doing opens a possibility window onto redemption for his senior. This is no exaggeration—Cash also recorded To Beat the Devil in 1970 and we are basically stipulating that Kristofferson’s genius, descended from Cash while also original to himself, helped rescue Cash from addiction and the whole deal there. We won’t be deep diving into the archive on this one—as we said we’re just keeping it local and breaking it down, so you’ll have to take my word on it or search it up your own self.

Here’s the first verse; the words speak for themselves:

It was wintertime in Nashville/ down on Music City Row/ and I was looking for a place/ and to get myself out of the cold/ to warm the frozen feeling that was eating at my soul/ keep the chilly wind off my guitar

A classic down and out in the big city piece of scene-setting. The singer is physiologically and psychologically frozen, a cold wind gusts across his art. The man needs a break.

My thirsty wanted whiskey/ my hungry needed beans/ but it had been a month of paydays/ since I’d heard that eagle scream/ so with a stomach full of empty/ and a pocket full of dreams/ I left my pride and stepped inside a bar

You might think that the operative nouns here would be “thirst” and “hunger,” but no. This is not a man with a thirst; this is a thirsty man. We also hear an echo of a now-ancient American past where a man with an empty stomach would go in search of, of all things, “beans.”

Anyway, he’s got no money, can’t really bring himself to care. So, a singer walks into a bar.

Actually I’d guess you’d call it a tavern/ cigarette smoke to the ceiling
and sawdust on the floor/ friendly shadows/ I saw that there was just one old man sitting at the bar/ and in the mirror I could see him checking me and my guitar/ and he turned and said/ come up here, boy, and show us what you are/ I said I’m dry, and he bought me a beer

The man in the mirror, the devil himself. The singer comes face to face with the man who checks him out and summons him over. Kristofferson then enters into a bargain–offers up the terms of an encounter: a beer on the old man’s tab. Score one for the thirsty man. The singer faces the old man; it’s to be a showdown. He doesn’t have much, but he’s got some “friendly shadows,” traces of an older map perhaps, an older memory.

I can’t help here but engage in a bit of presumption. When I play the song in my head, I want to hear “in the mirror I saw him casing me and my guitar,” (listen to the way he pronounces “guitar” on the track. Kristofferson was born in Brownsville, Texas in ‘36 and behind the laid back folksinger you can here some roots here baby).

If I could make one edit to the song, it would be to replace “checking me,” with “casing me.” What a great verb “to case” is.

Lexical Interlude: “To case the joint”

1. slang To observe a place in order to familiarize oneself with its workings in preparation for some criminal activity (often robbery). Judging from the security footage, those men cased the joint hours before robbing it.

2. slang By extension, to thoroughly examine a place. In this usage, no devious motive is implied. As soon as my kids walking into the hotel room, they started casing the joint, exclaiming about everything from the TV to the mini-fridge.

The seminal use of this verb phrase comes from Bill Callahan, formerly of Smog. Callahan is an odd duck—he is so artificial, so obviously self-created as an entertainer, that he has become almost post-authentic.  Callahan contains multitudes.

My favorite Smog album, well in the top two, is Red Apple Falls, which features “Ex-Con,” on which Callahan sings: 

Jean jacket and tie/ feel like such a lie/ when I go to your house/ I feel like I’m/ casing the joint

Devious motive implied.

=====

He nodded at my guitar and said/ it’s a tough life, ain’t it?/ I just looked at him/ he said “you ain’t making any money, are you?/ I said, you been reading my mail/ he just smiled and said, let me see that guitar/ I got something you ought to hear/ and then he laid it on me

The devil has a bead on the singer, and he’s not far off.  Yes he’s broke.  Yes he’s down and out.  Whaddaya want?

=====

Filmic Interlude I: The Long Goodbye

In Robert Altman The Long Goodbye, written by Leigh Brackett, the main character Philip Marlowe gets out of jail somewhere in the first act and heads to a all-purpose pit stop restaurant who’s owner apparently collects Marlowe’s mail. The dialogue is exquisite.

Marlowe: You got any messages for me?

Owner: Believe we’ve got a few over there. As a matter of fact, you’ll find my phone bill in there too.

Marlowe: I wouldn’t worry about that.

When you ain’t got nothing you got nothing to lose. Kristofferson’s got nothing to hide in his mail. Those bills go straight to the wastebasket.

=====

If you waste your time a talkin’ / to the people who don’t listen/ to the things that you are saying/ who do you thinks gonna hear?/ and if you should die explaining how/ the things that they complain about/ are things they could be changing/ who do you thinks gonna care?

there were other lonely singers/ in a world turned deaf and blind/ who were crucified for what they tried to show/ and their voices have been scattered by the swirling winds of time/ ‘cause the truth remains that no one wants to know

The devil’s words speak for themselves. The path of the troubadour is a dead end. The world has not ears to hear nor eyes to see. Truth tellers meet a bad end. Whiners gonna whine. It’s a strong opening bet, made, we presume, with his red right hand.

Well the old man was a stranger/ but I’d heard his song before/ back when failure had me locked out/ on the wrong side of the door/ when no one stood behind me/ but my shadow on the floor/ and lonesome was more than a state of mind

The singer is on familiar territory; he’s has been tempted by this cynical incantation, he’s not immune to tuning out his calling when out in the cold. Who is?

You see, the devil haunts a hungry man/ if you don’t want to join him/ you gotta beat him/ I ain’t saying I beat the devil/ but I drank his beer for nothing/ then I stole his song

This is the key verse in our little tale. You see, when we tango with the devil the devil usually gets to lead. That’s just the way it goes. But the thing about the devil is, his game is a bit of a bluff. A couple of low pairs, maybe. You just gotta call.

and you still can hear me singing/ to the people who don’t listen/ to the things that I am saying/ praying someone’s gonna hear/ and I guess I’ll die explaining how/ the things that they complain about/ are things they could be changing/ hoping someone’s gonna care

I was born a lonely singer/ and I’m bound to die the same/ but I’ve gotta feed the hunger in my soul/ and if I never have a nickel/ I won’t ever die ashamed/ ‘cause I don’t believe that no one wants to know

Kristoffeson flips it right around. The devil’s got a point; the singer may die dead broke, that’s fine. Songs are borne on the wind in any case. The thing is to have faith in your audience. To believe someone is out there, heart in their hands and ear to the wind. And to hold this faith as a mantra. That’ll keep ‘em guessing, cause then you’re not playing their game, you’re playing your own.

Overall, To Beat the Devil is a young man’s song. It’s got a confidence, a swagger, even a hubris. So, after drafting most of this piece I wanted to find a recent live version, see how it’s aged. I stumbled on a version from a live set with Lou Reed released in 2017. The set is part of The Bottom Line Archive, and it finds Kristofferson in a Waitsian stage of life. The voice is richer than ever, but he’s not exactly singing. Then again, that’s what they said about Dylan and it’s B.S. The voice is the voice; singing is just a category.

The set is interspersed with short interviews of the two songwriters. Here is Kristofferson’s spoken introduction that precedes To Beat the Devil. It is instructive.

Interviewer: The devil figures in some of your songs, you know there’s that silver tongued devil and he pops up from time to time. Who’s the devil? What’s the devil for you? What are your demons?

K.K.: Well, I, I’ll do that song then. Ahhh…

Interviewer: Is that a metaphor or is that something real for you?

K.K.: Well here’s a song called To Beat the Devil. Maybe it’ll explain it. I can’t.