In the late 2000s, singer-songwriter Justin Townes Earle wove together a gospel standard, a traffic jam, and a Jim Carroll memoir into a staggering meditation on death that became his biggest hit. As Jonathan Bernstein writes in his new authorized biography of Earle, What Do You Do When You’re Lonesome, “Harlem River Blues” is a “cheerful-sounding song with a chorus catchy enough to conceal its grim tale” of a man who travels to the tip of Manhattan and throws himself into the dirty water below.
“It took one listen to realize Justin had, at long last, written a hit, one with layers of meaning and interpretation and an internal rhyme scheme that displayed the seriousness with which he took his craft,” writes Bernstein, a senior research editor and writer at Rolling Stone, in the chapter excerpted below. “In his quest to modernize gospel, Justin struck gold with ‘Harlem River Blues.’ The song was an urban hymn — ‘I’ll Fly Away’ but with NYC traffic — that applied the tried-and-true gospel formula of setting songs about death to cheery melodies. Justin took the premise further: Why wait until the end of life to carry over? Why not go while you’re already in His good grace?”
Along with tracing the creation of “Harlem River Blues,” examining its many meanings — including how Earle spoke about his seminal track — the excerpt also digs into the creation of Earle’s 2010 album of the same name. The LP marked a new creative peak for the singer-songwriter, a “culmination of Justin’s development as a songwriter and a testament to his past few years of sobriety, even as it documented that sobriety collapsing,” Bernstein writes. The author also explores how this album cemented Earle’s legend status to a new crop of Nashville singer-songwriters (some of whom, like Caitlin Rose and Rayland Baxter, contributed to Harlem River Blues).
What Do You Do When You’re Lonesome, out Jan. 13, marks Bernstein’s first book, and was written with the full cooperation of the late musician’s estate. (Earle died in 2020 from an overdose.) The book digs into the backstories behind Earle’s most famous songs and chronicles his life, from the son of alt-country great Steve Earle to a revered talent in his own right, who often found himself struggling with mental illness and various addictions.
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Harlem River Blues would eventually become Justin’s biggest album; it flew off the shelves of record stores from Portland to Atlanta, earned him his first indie radio hit, and delivered him scores of new fans in increasingly large clubs across the country. The album was the culmination of Justin’s development as a songwriter and a testament to his past few years of sobriety, even as it documented that sobriety collapsing. Some songs were peppy odes to fried chicken, full of church organs and sloppy sing-along choirs and handclaps and raucous harmonica. Others were downcast tales of isolation and loneliness delivered as sparse, pedal-steel ballads or piano rockers. The breakout song, the title track, was a little bit of both.
“Harlem River Blues” is a fast, cheerful-sounding song with a chorus catchy enough to conceal its grim tale. The song tells the story of a man in New York City traveling to the northern tip of Manhattan to drown himself. “Dirty water gonna cover me over,” the narrator sings in the gleeful refrain, “and I’m not gonna make a sound.”
The narrator sounds jubilant as he outlines an informal will in the second verse: “Tell my mama I loved her, tell my father I tried,” Justin sings, “give my money to my baby to spend.”
It took one listen to realize Justin had, at long last, written a hit, one with layers of meaning and interpretation and an internal rhyme scheme that displayed the seriousness with which he took his craft. “I’m on a roll, mama, I’ve gotta go,” Justin’s narrator announces as he kicks off his journey uptown. In his quest to modernize gospel, Justin struck gold with “Harlem River Blues.” The song was an urban hymn — “I’ll Fly Away” but with NYC traffic — that applied the tried-and-true gospel formula of set- ting songs about death to cheery melodies. Justin took the premise further: Why wait until the end of life to carry over? Why not go while you’re already in His good grace?
“Even though I enjoy life pretty thoroughly, I’m of the opinion that it’s a pretty tough thing,” Justin once said when discussing the song. “People who say they’re going to kill themselves generally aren’t going to. People who make the decision to take their own lives usually don’t talk about it. They’re looking for a release.”
Justin laughed a dark laugh, then kept going: “I just decided to take that to a newer, sicker level. Make it a celebration.”
There goes the song’s narrator, skipping and singing up the FDR Drive, a parkway that carries several hundred thousand cars daily and isn’t generally known for leisure strolls. Is it a flight of fancy? A surrealist daydream? A manic episode? Or the calm confidence of someone who’s already made their final decision?
It wasn’t the first time Justin had written about suicide: He’d done it, to great effect, on the title track of Yuma, but that song hadn’t been a hit. He’d never had to answer questions about it in the same way.
Inevitably, the inspiration for “Harlem River Blues” changed depending on to whom Justin was talking.
“I have friends with fairly miserable lives and a few who actually took their own lives,” he said in 2011. “I talked with one friend about eight hours before he did it. And as he told me his plan, I saw a look of ease on his face I’d never seen. It was what he wanted to do, and [it’s] why the song has a celebratory feeling.”
But when a journalist asked about the album when it came out, Justin struck a different tone.
Interviewer: “There’s an undercurrent of depression to [Harlem River Blues]. Are you depressed?”
Justin: “Not in any way I haven’t been all my life.”
As for where the idea for the song actually came from, Justin’s story never changed: “Harlem River Blues” was inspired by a book, The Basketball Diaries, by Jim Carroll. Justin had read it as a teenager.
The 1978 cult memoir — a collection of drug-fueled diary entries pulled from the punk poet’s preteen years — was a totem of romanticized New York nonconformity. Justin zeroed in on a passage about a juvenile jinx Carroll and his friends dared each other to do in the sixties.
“Every crowd of young guys has its little games to prove if you’re punk or not,” Carroll writes. “Here in Upper Manhattan, guys jump off cliffs into the Harlem River, where the water is literally shitty because right nearby are the giant sewer deposits where about half a million toilets empty their goods daily.”
Carroll details the site of these jumps: a “series of minor cliffs” over- looking the polluted river at the northern tip of Manhattan, the highest one eighty-five feet tall. Then he, himself, makes the jump.
“I didn’t really think, I didn’t even take my sneakers off,” he writes. “I just jumped into this herky dream that lasted all the way down until I hit bottom. The feeling isn’t movement anyway, but rather being suspended in front of the sheer cliff, mid-air, with the waters rising up sharp and fast at you.”
Years after Justin first read the book, he had a vision. As he told it, it came while stuck in a hellscape of New York traffic. Driving into Manhattan one evening, Justin was stopped to a halt on the FDR Drive. Not knowing what to do, Justin called 11th Street bartender Kenny O’Connor for advice. O’Connor had a tip: get off the highway, and take the Third Avenue bridge into Harlem.
Justin took the suggestion, but traffic wasn’t much better. Stuck on the Third Avenue bridge, he peered into the black muck of the river Jim Carroll and his friends once jumped into.
The gospel music that informed “Harlem River Blues” would serve as the underpinning for the whole new album. These were the familiar sounds Justin claimed he’d heard walking past the neighborhood AME church as a kid. They were also the sounds that the album’s coproducer, and former Swindler, Skylar Wilson, honed during his year as the Sunday-morning church organist at a Black Baptist church in Murfreesboro.
Justin began recording Harlem River Blues at the studio House of David on May 17, as Nashville continued to recover from the flood.
This time, it was Justin and Skylar Wilson serving as producers. The atmosphere was loose, built on years of trust the two had developed. Wilson had played on Justin’s past two albums and had become his de facto studio bandleader and primary sounding board, the man entrusted with the execution of his vision. “He always knew the movie he wanted to make,” said Wilson, whose job was to manifest that movie.
The new album Justin was making — a sweeping millennial take on southern gospel prompted by the sights, sounds, and smells of New York City — felt fresh. Justin mixed in dispatches from his new hometown (“Workin’ for the MTA,” “One More Night in Brooklyn”) with tales from his worldly travels (“Christchurch Woman”) and songs that conveyed a new level of introspection and self-probing (“Learning to Cry,” “Slippin’ and Slidin’”).
To close the record, Justin reached back for one older composition, “Rogers Park,” a nearly decade-old song Justin had written after his brief stint in Chicago as an eighteen-year-old. Its premise — the tale of a young man lost and alone in a big city far from home — had become newly resonant.
The Harlem River Blues sessions pulled from the energy surging through Nashville: Jason Isbell and Old Crow’s Ketch Secor showed up to add guitar and harmonica on a few songs. When Justin and Wilson wanted the sound of a ramshackle choir for the chorus of “Harlem River Blues,” Wilson summoned some musician friends — “every hipster we knew” — to the studio.
Those musicians who appeared on short notice — Caitlin Rose, Rayland Baxter, Jordan and Alex Caress — were part of a budding community of early 2010s East Nashville songwriters who idolized Justin Townes Earle. They viewed Yuma, The Good Life, and Midnight at the Movies as gold standards of the type of music they strove to make.
“I didn’t think anyone was really doing it well until Yuma,” said Andrew Combs, one of Nashville’s many young and impressionable artists at the time. “We definitely held it on a pedestal.”
To many of them, Justin was a born-and-bred Nashville superhero. “We saw him in a way he never saw himself,” said Rayland Baxter, one of several singers who sang on Harlem River Blues.
As the 2000s turned into the 2010s, these artists started garnering attention for their own music. Baxter also sang on Own Side Now, the breakthrough debut from Caitlin Rose, which was also coproduced by Skylar Wilson.
Tristen Gaspadarek, a young songwriter who’d played alongside Rose at her twenty-first-birthday party that Justin had also played, was prepping her label debut, Charlatans at the Garden Gate. Rolling Stone would deem her “an artist worth watching.”
It was still several years before The New York Times infamously declared Nashville’s “it city” status. But the press was taking stock of this crop of millennial songwriters planting their flag in East Nashville, many of whom were influenced by Justin. They wrote their own songs and shared a lack of interest in, if not outright contempt for, the idea of writing for country radio. They preferred older stuff: Guy Clark, Mickey Newbury, “Dead Flowers.”
Acoustic music in East Nashville wasn’t new, but this crop of art- ists was a generation younger than neighborhood stalwarts like Gillian Welch, Todd Snider, and Elizabeth Cook, and they made for a sexier story. Many of them arrived on the east side ready to carve out their own spaces, make their own friends, and find new rooms to occupy. Baxter, Rose, and Gaspadarek were locals. Most were not; there was Combs, who’d arrived from Dallas eager to re-create Heartworn Highways; Jeremy Fetzer, a guitarist from Ohio; Nikki Lane, a fashion-forward South Carolina transplant; Jonny Fritz, an oddball Virginia songwriter who adopted the surname Corndawg; Brian Ritchey, an Indiana-bred friend of Justin’s who formed the talented yet unfortunately named trio Korean Is Asian with Jordan and Alex Caress; and Derek Hoke, a Georgia songwriter who worked at the Belcourt Theatre.
Most of these artists revered Justin, and he returned the praise. He was quick to shower local songwriters with encouragement and kindness, to let them know he’d been listening, that the songs they were writing mattered. When he was back in town, Justin would show up to old coffee-shop haunts, chat up the baristas, find out what band they were in, then go see that band play a show on a night off. “It was the first time we had someone in our corner,” said Jordan Caress. “And it was cool that it was him.”
On May 25, Justin headlined a flood-benefit show with various local musicians at the 5 Spot, the dimly lit East Nashville dive where his disciples congregated. Justin presided over the proceedings, likely proud as he beheld the singer-songwriter scene blooming, once again, out of his hometown: These songwriters, just a few years younger, had carved out their own space that was being appreciated much more than the Swindlers ever were. Justin wanted to do what he could to support it, and he told the artists as much.
But behind the scenes, throughout recording and mixing Harlem River Blues that May, Justin was struggling. He continued to relapse.
He’d spent the month crashing in the spare room of his friend and photographer Joshua Black Wilkins. At night, alone in his hometown, Justin sat in the dark quiet of the guest room and gulped down cans of cheap beer by himself. Wilkins knew, by then, that Justin had started drinking: They’d been to bars together, and every so often, when Justin was out, Wilkins came into the guest room to sweep out the wreckage of empty beer cans Justin had stuffed underneath the bed.
But Justin avoided any outright communication with his old friends about what was going on. Instead, one night in Nashville, he tweeted into the void: “There’s nothin wrong with warm beer.”
A year later, Justin would claim that he recorded Harlem River Blues while “doing an eightball of cocaine a day and choking down pain pills, you know, just loaded.”
Over the past year, he’d written the songs, so he said, during the day, while he was still pacing his vodka intake and hadn’t yet started on cocaine, finishing his writing by five in the afternoon.
“Usually by that time I was what most people call drunk,” he said, “then I’d go out and get what I consider drunk.”
It was a dark and abrupt change in narrative to hear Justin talk about writing and recording his most acclaimed body of work in the height of a relapse. Was the myth haunting him again? He’d spent the past three years preaching that great art wasn’t contingent on getting fucked up — or on fucking up one’s life. But as much as he’d once worked to dispel the myth, he propagated it anew in the story he told about Harlem River Blues.
Anyone watching Justin in the studio could appreciate that he was creating brilliant art despite the drugs and alcohol. At one point in recording, when Justin seemed possibly too intoxicated to credibly play his instrument, Wilson politely suggested that maybe Harlem River Blues didn’t actually need acoustic guitar. Justin trusted Wilson’s instincts. After Harlem River Blues was finished, Justin flew back to New York, this time to an empty apartment: He’d given Keesecker thirty days to find a new place while he was out of town. For the first time, he was liv- ing in New York City by himself. There wasn’t much use in sitting around alone. Within twenty-four hours of landing in New York, Justin was back at the 11th Street Bar.
Excerpted from What Do You Do When You’re Lonesome: The Authorized Biography of Justin Townes Earle by Jonathan Bernstein. Copyright © 2026 Jonathan Bernstein. Available from Da Capo, an imprint of Grand Central Publishing, a division of Hachette Book Group, Inc.
