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

Epigraph:

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

Craig Finn

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

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

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

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

Jessamine opens thusly:

I met Jessamine in Cherry Hill

Her dress all done in daffodils

The sticker on her skateboard said, “Speed kills”

And yeah, it probably did just what it said

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

Verse II adds a little more context.

I only knew her for like three weeks straight

And the whole time we were wide awake

You know “Trenton Makes, the World Takes?”

She had it spray-painted over her bed

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

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

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

We used to hang around her room

Getting off on all the gloom and the doom

Watching cavemen in the cartoons

Playing xylophones made out of bones

She was sexy, but still death-obsessed

She said the bloodshed makes such a mess

But you really don’t even have to market it

Yeah, it pretty much sells itself

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

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

I should’ve asked her before she departed

How did all these wars get started?

Why do rival crews show up to the same parties

If they hate each other so much?

It’s like they’re secretly in love

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

Verse V and Chorus II go like this:

She said, “Suspicion isn’t wisdom

And the drones look just like doves”

And there was something laying siege to her kingdom

But she never really said what it was

While the incense turned to ashes

And the sunrise was unsure

Jessamine musta had some dreams

But she never really said what they were

Yeah, she never really said what they were

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

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

We kinda ended how we began

With Jessamine meeting a man

And liking that man just a little bit more

Than the boy she had before

I hadn’t even seen her since

I guess this new guy was some kind of prince

I guess his castle was a front for some fence

And then the whole damn city got warm

And they were trying to ride out that storm

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

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

‘Cause the rain is inconsistent

And the thunder is insincere

‘Cause it makes a big commotion

But eventually it clears

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

I went out to San Francisco

And some sailor stole my shirt

I was sitting on the passenger side in a taxi

The first time that I heard

That she was probably speeding

And no one else was hurt

Jessamine must’ve had some dreams

But she never really said what they were

Yeah, she never really said what they were

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

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

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

Dedication:

For goth girls everywhere.

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

Craig Finn on Nightlife and Adult Relationships I: Most People are DJs
On Subcultures and Scenes in Craig Finn’s “It’s Never Been a Fair Fight”
On Craig Finn’s “A Bathtub in the Kitchen”
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In Defense of Conor Oberst

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

In Defense of Mark Kozelek
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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 & Fire, Prisoner, 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.

In Defense of Conor Oberst
In Defense of Mark Kozelek
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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.