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The Ballad of Justin Townes Earle

He was a brilliant songwriter who built his own legend but couldn’t outrun the darkness that came with it. Earle's wife, friends and collaborators recall his magnetic personality, the real-life stories behind his songs, and his heartbreaking final days
Joshua Black Wilkins

One day in the spring of 2018, Jenn Marie Earle was washing dishes in her Portland, Oregon, home, when her husband, Justin Townes Earle, walked into the kitchen with his guitar to play her a song he’d just written. 

As Justin started singing, Jenn Marie began to cry. On its surface, “Ahi Esta Mi Nina” was the tale of a Puerto Rican father attempting to reconnect with his estranged daughter after a long prison stint. But Jenn Marie realized that the song was ultimately about her husband’s pain. His career had leveled off in recent years, and a sense of isolation had set in as he became increasingly worried about being able to provide for his wife and baby daughter. Justin was locking himself inside a dark room off the basement for hours to write, communicating with Jenn Marie through a grate connected to the kitchen upstairs. “If you need me,” Justin would shout, “just stomp your hoof, my little dear.” 

“I’d seen him starting to become more distant, in many ways,” Jenn Marie says. “That song, to me, was an admittance, of choosing the fate of being locked away from what means the most to you.” The album Justin was writing in that unlit basement study, the last album released while he was alive, would be called The Saint of Lost Causes. “I think he was admitting that he was defeated, in a lot of ways,” Jenn Marie says. 

It had been less than a decade since Earle released his breakthrough, 2010’s Harlem River Blues, which set songs about subway conductors, addiction, and cramped Brooklyn apartments to old-time gospel, folk, and country-blues styles. By that point, he was transcending omnipresent comparisons to his father, country hitmaker turned folkie Steve Earle, and was poised to become the first solo superstar in the genre of commercial roots music that had come to be known as Americana.

Onstage, Earle was an electrifying presence: six-foot-four, dressed in vintage suits, playing in a fiery style of finger-picking he’d picked up listening to the bluesman Mance Lipscomb. He assumed the public persona of a world-weary troubadour, one worthy of his cursed namesake, the self-destructive country-folk genius Townes Van Zandt, a friend of his father. He could be Old Testament-intense one moment, sardonically witty the next, bantering with hecklers and tossing off one-liners like, “I haven’t swayed from Bruce Springsteen’s formula of girls, cars, and sex,” before adding, “Oh, and Mama.” 

Earle was funny, caring, and obsessed with esoterica involving antique Rolexes and baseball history. His magnetic persona left a permanent impression on those who knew him. “He lived the life that you would read about some other country legend living,” says early tourmate James Felice of the Felice Brothers. The son of an entertainer who understood showbiz better than most, Earle embraced and solidified his own legend on and off the stage, sharing tragicomic stories about his adolescent heroin overdoses and bar fights that cost him teeth. 

But that persona also masked problems that only worsened as Earle’s career plateaued. He wrestled with mental-health struggles and self-doubt, and like his father, he struggled with addiction. “The fact that I survived my twenties is a miracle,” he once said, “and I believe that wholeheartedly.” 

As the years passed, Earle’s insecurities grew. “There was a huge part of Justin that didn’t believe in himself,” says Jenn Marie. “He saw the music business changing. . . . When his [2014 and 2015 albums, Single Mothers and Absent Fathers] came out, he was disappointed they didn’t do so well. I think that’s where a lot of his darkness, his struggles with substance abuse and addiction, started to come to the surface in the last few years: him feeling like he wasn’t good enough.”

After writing the songs for The Saint of Lost Causes in 2018, Earle entered rehab, a process he’d been through more than a dozen times, then headed directly for the studio. The unusually vulnerable album seemed like an occasion for a career turnaround, and executives at his label, New West Records, were thrilled. But by the time Earle hit the road in the fall of 2019, he was drinking again, so much that bandmates wondered if they’d be able to finish the tour. 

In January 2020, Jenn Marie helped Earle rent an apartment in Nashville, where he could temporarily live alone and focus on a flurry of musical projects. He embarked on a solo tour in March, only to shut it after one show, as the pandemic halted concerts nationwide. Forced to quarantine in Nashville, Earle floundered. “He needed an audience,” says friend and producer Steve Poulton. “He was used to having one: putting that energy out, and getting it back.”

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Earle in the studio while recording his final album, “The Saint of Lost Causes.” Joshua Black Wilkins

Earle considered producing a Nashville hip-hop act and contemplated several future albums, including a Billie Holiday tribute with the Preservation Hall Jazz Band and a record of duets with artists like Yasiin Bey (the rapper formerly known as Mos Def) and Brian Fallon of Gaslight Anthem. Earle, with his manager and close confidant, Larry Kusters, began planning a livestream series in which he would perform with guests and expound on his favorite topics — baseball, the Delta blues, Civil War battles. The working title for the show was Justin Townes Earle: Misbehaving.

But according to friends and family, Earle continued to struggle with addiction. Though he was only 38, two decades of chemical dependency had taken a toll on his body. On July 21st, he was admitted to a Nashville hospital for pneumonia and underwent a serious lung surgery that, according to Jenn Marie, was a result of the long-term effects of his drug and alcohol use. By the time he left the hospital on August 2nd, his doctor warned him that his body would not be able to keep up if he kept drinking. “We thought that would be a wake-up call,” says Jenn Marie.

Justin felt otherwise. “He always used to say to me, ‘The Earles don’t die, we’re invincible,’ ” says Kusters, who visited Earle after he left the hospital. A few weeks later, on Thursday, August 20th, Kusters spoke with an upbeat, if restless, Earle over the phone. “He was getting a little bit antsy: ‘When can we go out on the road?’ ” says Kusters. According to The New York Times, that same day Justin called his father, who told his son, “Do not make me bury you.” 

“I won’t,” Justin replied. 

Then, no one heard from him. When the Nashville Police Department performed a welfare check Sunday evening, they found Earle dead in his apartment. A toxicology report determined he died of an accidental overdose due to a combination of alcohol and cocaine that was laced with fentanyl, the deadly opiate responsible for the deaths of Prince and Tom Petty, among many others.

Earle became yet another victim of the opioid crisis, a topic he wrote about on his last album and had been discussing in stark terms onstage for years. “We have for so long looked at people who had addiction problems … we ask them the wrong questions,” he said in 2018. “We say, ‘What is wrong with you?’ The problem is, they hurt. So you don’t ask them, ‘What’s wrong with you.’ You ask them, ‘Why do you hurt?’ ”

Earle’s death caused an outpouring among fans like Stephen King and Billy Bragg. Steve Earle paid tribute with J.T., an album of his son’s songs. “The record is called J.T. because Justin was never called anything else until he was nearly grown,” Earle, who declined to speak for this article, said in a statement. “For better or worse, right or wrong, I loved Justin Townes Earle more than anything else on this Earth.”

“Justin shaped so much of the broader, younger perspective of what Americana music was,” says Earle’s former manager Nick Bobetsky. Earle’s primary musical partner, Adam Bednarik, says, “He changed the lives of a lot of other people around him for the better.” 

Singer-songwriter Jessica Lea Mayfield, who frequently toured with Earle, described his gift more simply: “He was able to explain trouble better than most.” 

In the late Seventies, Steve Earle met Carol Ann Hunter at a Nashville bar where she worked. They married in 1981, and Hunter gave birth to Justin a year later. By the time Justin was four, in 1986, his parents had separated; that year, Steve Earle became an unlikely country star with his debut, Guitar Town. One song, “Little Rock ’n’ Roller,” was a touring musician’s promise to his son: “One of these days when you’re a little older,” Steve sang, “you can ride the big bus and everything will be alright.”

Justin spent his early childhood with his mother in a then-rough neighborhood in South Nashville, where he was exposed to drugs and dropped out of school in eighth grade. “I had the shaved head and the rat tail and wore the Jams and Air Jordans,” Justin said in 2009. 

When Justin dropped out of school, he began to see more of his father, touring with him as a guitar tech and later doing odd jobs for his dad’s label. By the mid-Nineties, Steve was sober, having been forced to kick a heroin addiction while briefly serving time in prison on drug charges in 1994. 

In the late Nineties, Justin joined his first real band, the Swindlers, a collection of kids whose fathers were successful Nashville songwriters and musicians — “Music Row brats,” as one of them, Dustin Welch, puts it. The Swindlers’ headquarters was a backyard studio on Welch’s family property known as the Chicken Shack, a dusty shed full of recording gear, where Earle and Welch lived on and off as teenagers. The boys spent their nights partying and obsessing over their fathers’ blues records, putting their fingers on the spinning vinyl to slow them down and study the instrumental parts. 

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Earle with his mother, Carol Ann Hunter, backstage at the Grand Ole Opry in 2008. Joshua Black Wilkins

By the time he was a teenager, Justin was writing profoundly adult meditations on loneliness and despair like “Rogers Park” and “Down on the Lower East Side.” It soon became clear the Swindlers would serve as a vessel for his blossoming songwriting. “He was this force of nature,” says another Swindler, Skylar Wilson, who produced several of Earle’s early records. “Everybody was trying to keep up.”

Even when the band members worked to break free of their fathers’ influence, it loomed over them. On the Swindlers’ first tour, in Oklahoma City, they panicked when they realized it was Father’s Day. Each bandmate began frantically calling his dad. “Dumbass,” Welch remembers Steve Earle telling Justin, “that’s next month.”

As a budding songwriter, Justin was eager for his father’s approval, which didn’t come easily early in Justin’s career. “Steve knew how incredible of a writer [his son] was — he let me know that — but he couldn’t always let Justin know that,” says Welch. Once, after the Swindlers ended a show with a newly written original named “Maria,” Steve asked Justin about the Elvis Costello song he had closed with. More than a decade later, Justin was still proud of the unintentional compliment. 

As Justin grew into his own as an artist, Steve increasingly became one of his son’s biggest public cheerleaders, but privately Justin still hungered for his father’s approval. “I don’t know if he ever listened to Harlem River Blues,” Justin told a journalist in 2012. “I’ve gone over [to Steve’s house] a few times and still found the same, wrapped copy of it sitting on the countertop. My dad means well, but he gets all over the place sometimes. He’s just like me, scattered as shit.”

One of the first of many times Justin would mythologize his complicated relationship with his father in song was on “Decimation of a Southern Gentleman,” a frighteningly personal unreleased Swindlers-era tune that Earle soon abandoned: “You ever get the feeling you were gonna die in the streets that you were raised in? Doing the same things your daddy done?”

Eventually, the Swindlers grew apart, and Justin began focusing on his own music. In 2006, Earle and a friend, the singer-songwriter and photographer Joshua Black Wilkins, decided to embark on a joint solo tour. Wilkins suggested that Earle use his middle name, Townes, on the road. Earle agreed, and took the idea a step further, getting “Townes” tattooed below his throat.

Earle was proud to be a working artist in an industry that seldom valued actual musicians. On one of his first tours, he became enraged when a stranger insulted a street busker. “We walked past a street musician, and the guy wasn’t very good,” remembers Poulton. “Somebody said under their breath, ‘Get a job,’ and that just incensed Justin. He was like, ‘Don’t you ever talk to that guy like that. If you tried half as hard as that motherfucker is trying, you’d really have something.’ ”

For all his prodigious gifts, Justin was never free of the shadow of his father. Their complicated relationship ended up becoming one of his most enduring themes as a songwriter, from 2009’s “Mama’s Eyes” (“I am my father’s son”) to 2012’s “Am I That Lonely Tonight?” (“Hear my father on the radio”) to his 2015 album, Absent Fathers. Justin wasn’t concerned with his parents hearing his songs that addressed them bluntly: “I always had to deal with it in a public format,” he said. “Why shouldn’t they?”

In the early days of Justin’s career, father and son enjoyed exchanging playful jabs in public. “The . . . advantage Justin has is he can’t fucking do anything else,” his father told the Nashville Scene in 2008. “So he knows he better make it work.” Performing at an intimate record-store gig in 2010, Justin was interrupted by a phone ringing at the side of the stage. When he looked up, his father was answering a call from his wife. “We’ll just wait till he’s done,” Justin joked to the crowd. 

“Everything Justin ever learned, he learned from his dad,” says Wilkins. As time went by, Justin often seemed to empathize with his father. “I can’t really blame him all that much,” Justin said of Steve in 2012. “I’m turning out to be more like him than I ever thought I would.”

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Justin with his father, Steve Earle, on the subway in New York City in 2011. Joshua Black Wilkins

By the time Earle released his first album, in 2008, he was 26 and enjoying the first sustained period of sobriety of his adult life. He slowly built a rabid fan base playing several hundred shows a year as an acoustic duo with his former Swindlers bandmate Cory Younts. The two logged tens of thousands of miles in a Ford pickup, with Earle often driving so outrageously fast that one time in Florida the duo feared for their lives when the gas pedal got stuck to the floor. Spending so much time together led to tension; Younts remembers the time they pulled over to the side of a highway in Arizona, stepped outside the car, “swung at each other for a while,” got back in, and kept driving.

When he wasn’t swinging his fists at his bandmates, Earle endeared himself to those in his orbit, rehashing larger-than-life tall tales about his past: how he was regularly smoking weed by age 11; the time he said a polite hello to Andy Griffith in a hotel lobby, to which Griffith replied, “Fuck you, son.” “He had a canon of stories and jokes that sort of explained himself,” says tourmate Samantha Crain. “It was like, ‘I want you to know so much where I’m coming from.’ He really just wanted to connect with people.” Earle’s one-liners were an art form: “He once told me I was so skinny that I could hang glide on a Dorito,” says Mayfield. “It was impossible not to be smiling or laughing when you’re around him.” 

Earle dished out worldly knowledge on everything from the wonders of LSD to what constitutes authentic Mexican cooking to where to find the best roadside antique shops. “Justin would tell these fantastical stories, and after the session I’d go home and Google what he said and I’d be like, ‘Holy shit, he’s right,’ ” says Mike Mogis, who produced one of Earle’s albums. “It’d sound like bullshit coming out of his mouth, but it’s not.” 

Sometimes, it was bullshit. Jenn Marie laughs recalling the time Earle, who played soccer as a child, tried to explain to her friend, a professional soccer player, the intricacies of the sport. “That happened all the time,” she says. “He really did study everything. He would stay up so late at night, reading books and watching interviews.”

Earle’s former agent Andrew Colvin remembers going tubing with Earle on the Gulf Coast. “I have a vivid memory of Justin on that tube, tattoos all over him, smiling as big as a human can smile,” he says. At the same time, Earle’s congeniality may have served as a useful way to avoid sharing his private thoughts. “We spent every day together for three years,” says bandmate Bryn Davies. “On one hand, I felt like he would give me the shirt off his back. On the other hand, I never had any idea what he was thinking.”

“Justin was like a big floppy-footed puppy dog that’s, like, really pretty dangerous and doesn’t know his potential, but also knows it very well and is kind of a giant. But also kind of a puppy,” says singer-songwriter Jonny Fritz, one of his former opening acts.

Earle relished mentoring younger artists, giving advice that often seemed like it was intended for himself as much as anyone else. When teenage singer-songwriter Sammy Brue joined Earle for his first national tour, Earle gave him regular lectures on drugs. “He rammed it in my head that I shouldn’t touch this stuff,” says Brue. “He wanted to protect me.” 

Earle was often exceedingly generous. He would give his opening acts and bandmates extra cash while on tour. When Earle heard that Fritz had lost a favorite shirt, originally purchased at a Virginia gas station, Earle tracked down the identical shirt for him. 

That sense of loyalty helped place Earle at the center of a quickly growing roots-music revival based in East Nashville. When Earle recorded Harlem River Blues, everyone from Jason Isbell to Old Crow Medicine Show’s Ketch Secor to up-and-coming songwriters like Caitlin Rose showed up to play or sing on the record. “He was my hero,” says Rose. “I remember getting into Justin’s [first] records and thinking, ‘I didn’t know that people could still do this.’ ”

Written during a period of relative sobriety, Harlem River Blues added gospel, R&B, and soul textures to Earle’s fast-improving songwriting. It proved to be his breakthrough, though Earle seemed to sabotage its rollout. Two days after its release, he was arrested in Indianapolis and charged with battery, public intoxication, and resisting law enforcement after trashing a dressing room and allegedly hitting the club owner’s daughter. (Earle denied the charges, which were eventually dropped.) 

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Earle performing in 2006. Joshua Black Wilkins

Within 10 days of releasing the album, Earle was back in rehab, postponing the most high-profile tour of his career. Harlem River Blues nonetheless became his biggest-selling record, leading to surging Bonnaroo crowds and Letterman appearances. “Between the lineage and the name and his fashion and the bad-boy reputation, Justin had the makings of someone where you think, ‘If everything works out, this guy could be a fucking icon,’ ” says Justin Eshak, his manager from 2010 to 2012. “He reminded me a lot of Amy Winehouse, in a weird way . . . I thought, ‘This is a guy who could be on posters on people’s walls.’ ”

Earle appeared outwardly unflappable throughout this turbulent period, with one notable exception. In the summer of 2010, shortly before the release of Harlem River Blues, one of Earle’s heroes, Levon Helm, asked to join him onstage to sing a verse of “The Weight.” “It was the most excited I ever saw him” says Lauren Spratlin, Earle’s former road manager and ex-girlfriend, “I remember being on the road with him and him obsessively playing [the song] over and over. He was like, ‘I can’t fuck this up.’ ’’

After yet another rehab stint, Earle was prescribed Suboxone, a drug given to patients fending off opioid addictions. By the time he appeared on Letterman for the second time, in February 2012, he looked and sounded like a different singer than the one who’d appeared on the show just one year earlier: “Mama, I’m hurting,” he sing-shouted, “in the worst way.” 

Around this time, Earle burned many of his closest personal and professional connections. Longtime bandmates like Younts and Davies had stopped touring with Earle, causing the singer to lash out, as he often did when he felt he was being abandoned. When Spratlin signed on to tour-manage Jason Isbell after breaking up with Earle in 2013, the singer erupted at both her and Isbell. 

“For us, it was the end of a really good era,” says Wilson, who worked on Earle’s first four records, “but at that point, it had already run its course.”

“I was expecting the wheels to come off,” says Earle’s longtime friend and former Swindlers member, Andy Moore, of this time. “And quite the opposite happened.”

That same year, he began dating Jenn Marie Maynard, a teenage acquaintance he reconnected with at a show in her hometown of Salt Lake City. Earle was smitten with Jenn Marie, a former athlete who owned a yoga studio and was almost as tall and lanky as him. “ ‘I’m over the moon about her,’ ” Moore recalls Earle telling him at the time. “ ‘And want to know the best part? I don’t have to bend down to kiss her.’ ” In October 2013, Justin and Jenn got married — just the two of them and an officiant — in blue jeans in the woods above Lake Tahoe. “To see a grown man just sobbing in happiness, it was really special,” says Jenn Marie.

At the time, Earle’s career was at a crossroads. His deal with his supportive first label, Chicago’s Bloodshot Records, expired after he released his midnight-soul record Nothing’s Gonna Change the Way You Feel About Me Now, in 2012. In late 2013, he got into a public spat with a label he’d briefly signed with, co-owned by Mumford & Sons’ Ben Lovett. “I have now learned that you can never trust a bunch of babies that ain’t worked a day in their lives,” Earle tweeted of the label, which he departed before releasing any music. “Just found out I won’t be making a record for a while due to a bunch of pussies in an office.” Around that time, Earle recorded a double album, but ended up releasing the material as two separate records: Single Mothers and Absent Fathers. Both received notably less attention than his previous few albums. 

Meanwhile, Justin and Jenn Marie were getting tired of Nashville, the only city in the world where a moderately well-known singer-songwriter with the last name “Earle” might get stopped everywhere he went. “He was so sick of being Justin Townes Earle,” says Jenn Marie. The couple moved to a remote area on the Northern California coast, which Earle described as “a town of skittish hillbillies that all grow marijuana.” At first, Earle seemed to thrive out West. In California, he devoured books on the Civil War and spent his mornings walking the couple’s dog on the rocky beach and gathering rusted objects that had washed ashore to display in the yard. 

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Justin with his wife, Jenn Marie, in Gulf Shores, Alabama, 2015. Courtesy of Jenn Marie Earle

In the early years of their marriage, Jenn Marie toured with Justin, and the couple spent free time on the road scouring down antique shops. Earle was a voracious spender, accumulating enough old maps, rugs, vintage Rolexes, and $500 gold-plated lighters to require several storage spaces in Nashville. “I remember him yelling at his business manager, demanding the extra money for this fucking gold lighter,” says Jenn Marie. “He always had an admiration for old things that told stories.” Earle’s free-spending ways concerned his various managers. “I’d have to have conversations with him where I’d be like, ‘Dude… ‘ ” says Bobetsky. “It was definitely intense to manage.”

Jenn Marie grew accustomed to Earle’s eccentric habits. He spent his time in the green room before shows transfixed by full-game replays of the 1967 World Series. “There would be blunts everywhere, and he’d be pacing around the room watching this game that he’s seen 100 times,” says Jenn Marie.

Earle still electrified crowds, but offstage, he was struggling with various mental-health problems. Jenn Marie is reticent to go into detail but wants the world to know that as much as Earle’s addictions tended to be romanticized, his day-to-day existence, sober or not, was often full of deep, unglamorous suffering. “A lot of famous people who are charismatic and handsome and stylish and talented, they struggle with mental illness, too,” says Jenn Marie. “I wish people knew how much he did struggle with what they couldn’t see, and what he didn’t write about.”

Earle had long been prescribed medication to help with mental-health issues (“He was on medication morning, noon, and night,” says Jenn Marie). But he had trouble stabilizing his treatment, cycling through doctors on the road who gave differing diagnoses and often prescribed medication over the phone. In California, Earle stopped taking Suboxone. “That was around the time his other addictions started coming back,” says Jenn Marie. Earle smoked medical-grade weed, and according to Jenn, he’d often be “high from the time you wake up until you go to sleep. That’s how he functioned.”

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Earle signs souvenir pennants at his and Jenn Marie’s loft in Nashville, 2014. Courtesy of Jenn Marie Earle

A few years later, Earle would tell Jenn Marie that their seemingly idyllic tenure in California had actually been a particularly isolating period. He was removed from old friends and struggled to write songs without the din of city life. “He was always going to feel lonely, to some degree, even when he was surrounded [by love],” says Jenn Marie. “He was really attracted to the stories and damage of things, and he didn’t write happy songs. There’s a certain level of staying in a deep, more depressed state of mental health if you are constantly only surrounding yourself with stories and shows and thoughts that are dark and deep. He wasn’t really giving himself a chance to be surrounded by positivity. He didn’t open the door, fully, to that. It was just cracked.”

On the West Coast, old friends had a hard time reaching Earle. “He’s probably lost 30 iPhones in the past 10 years,” says Wilkins. When Omaha-based musician Mike Mogis was enlisted to produce 2017’s Kids in the Street, he tried calling Earle 10 times before finally getting him on the phone. Before one of those scheduled calls, Earle informed Mogis he couldn’t speak because he was at Chicago’s Wrigley Field, watching his favorite team, the Cubs, play in the World Series.

By the time Earle made it to Omaha to record, he knew he was going to become a father. The prospects of fatherhood loomed large for Justin, who would later ponder aloud, before his daughter, Etta, was born, that if she ever wanted to become an artist of any sort, she could drop her “Earle” surname and go by her first and middle names if she preferred.

Once Etta was born, Earle was overjoyed. “Etta says bye-bye in the sweetest little voice,” he wrote on Instagram when his daughter was a year old. By then, Justin and Jenn Marie had relocated to Portland, Oregon. “It was so not the person people want to think he was,” says Andy Moore. “He was over the fucking moon about [Jenn], over the fucking moon about the baby. There is a well-adjusted Justin that I know to have had some of the deepest and most heartfelt conversations, where we talked about the shortcomings of our own families and our paternal lines: ‘How are we going to be better than this?’ ”

Becoming a dad helped Justin feel closer to his own father. “We’ve been talking more lately, it’s kinda weird,” Steve told Justin on Steve’s SiriusXM show shortly before Etta was born. “You started calling me all of a sudden in the last few months.” 

But even as he grew closer to his father, Justin still battled feelings of inferiority. In the last few years of his life, he confided to his guitarist Paul Niehaus that, because his own songwriting was so personal, he thought his father, who alternated between autobiography and literary character sketches, was the superior songwriter.

“At certain moments of time, I don’t think that he felt he was loved enough,” says Kusters. “Onstage, Justin never had a second of a doubt that his music and lyrics were loved. But in a hotel room or tour bus at two in the morning, he would question that: ‘How good am I as a musician?’ How good am I as a person?’ ”

Now in his mid-to-late thirties, Earle admitted to those closest to him that he wasn’t yet ready to fully deal with his deeper struggles. “He said to me a couple of years ago that his demons were snipping at his heels, and he was ready to face it,” says Jenn Marie. “But that immediately came with him deciding that he wasn’t ready to face it.”

Earle often disguised his most revealing moments in old-time blues and honky-tonk styles that made it seem like he couldn’t possibly be singing about himself. But on the very last song of The Saint of Lost Causes, the introspective country confessional “Talking to Myself,” he was as blunt as he’d ever be: “I’m in a lot of pain and I need some help/I don’t dare tell nobody else.” 

“It’s really sad thinking about that being his last album,” Bobetsky, Earle’s former manager, says through tears, “because the writing’s on the wall.”

In his last few years, Earle reconnected with many of his old friends. When Welch surprised Justin at one of his gigs in 2018, in Austin, Earle sprinted out of the green room and jumped on his old Chicken Shack roommate, wrapping his arms and legs around him. After nearly a decade of not playing together, he invited his old collaborator Cory Younts to play on The Saint of Lost Causes. This past spring, he reconnected with several old Nashville friends, including Skylar Wilson.

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Earle in 2019. Joshua Black Wilkins*

In Nashville, during his final eight months, Justin spent more time than he had in ages with his mother, Carol Ann, with whom he remained close. Earle had helped buy her a house earlier in his career. “She was always just worried about him, and loved him to death,” says Welch. 

Jenn Marie and Etta, whom Justin had taken to calling Etta-belle, visited Justin on several occasions throughout 2020. The last time the family was together, a few days before Justin’s death, Jenn and Justin revisited their favorite antique shops and took Etta to parks Justin had played in as a child, including his sentimental favorite: Nashville’s Dragon Park, named for its sea-serpent sculpture, where Earle played soccer as a kid. When, at the end of their trip, Jenn Marie and Etta got into their car to go to the airport, they rolled down the windows. Justin screamed, “I love you,” at them, and they screamed it back. 

“Fucking heartbreaking,” Jenn Marie says, thinking back on that moment. “I wish I could’ve just grabbed him and said, ‘You’re coming home. Fuck business. Fuck convenience.’ But he wouldn’t have come, anyway. He would’ve figured out some kind of excuse to be alone, because he was like that.”