Considering that he’s now 22 years sober from a cross-addiction cocktail that could rival Keith Richards’ and has survived seven weddings and divorces—two with the same woman—it’s odd to hear Steve Earle talking about death. And, as he roars back with the brazen country So You Wannabe an Outlaw, it’s not merely contemplation inspired by losing old friend and noted Texas songwriter Guy Clark last year, though that loss clearly inspired Outlaw’s “Good-Bye Michelangelo.” This rumination is a practical, life-informing consideration that’s settled long after the 62 year old’s dangerous living was done.

“It was coming from a long time,” he offers, his equanimity about losing a key mentor underscored by a dark laugh. “There were people who thought I’d be gone a long time before Guy.”

Dressed in a black T-shirt, dark jeans that hang a little slack and Ariat boots, there’s nothing you’d notice about the guy with the trimmed beard except the penetrating eyes that are always moving. Earle’s intelligence is acute, and it almost drives him.

Gathering his thoughts on a beat-up leather sofa in a sprawling rehearsal studio by Nashville’s Cumberland River, Earle does what he does best: plows on with his narrative. “I spend a lot of my life preparing to die. I follow Ram Dass—for the last 20 years, reading his writing about preparing. I practice yoga every day and go to the gym. I have my 12- Step programs. But if you ask Ram Dass, he’d say, ‘You’re not supposed to do anything.’”

It seems unthinkable for Earle to stand still. Since breaking through at 31 with the porous blue-collar rockcountry Guitar Town, the San Antonio-raised songwriter showed a predilection for action. Even during what he’s referred to as his “vacation in the ghetto,” he managed to get busted with heroin and a gun, ending up doing jail time; that’s where sobriety took root. Along the way, he’s written a play, a book of short stories and a novel, had his own label, been an aggressive anti-death penalty activist, produced Joan Baez, acted in HBO’s acclaimed The Wire and Treme (as well as writing and recording songs for both of those) and contributed to the acclaimed film Dead Man Walking.

Stillness seems impossible. Even musically, he’s restless. His body of work leans toward rock (The Revolution Starts Now, The Hard Way, I Feel Alright), straight-up bluegrass (The Mountain with the Del McCoury Band), post-hip hop (Washington Square Serenade) and folk (Train a Comin’). It makes his return to country— something left far behind— somehow both surprising and inevitable.

“I made a country record on purpose,” he concedes, making sure that his intentions are spelled out. “The Low Highway was more of a folkie-country record, based on Harvest and After the Gold Rush. This one is about rehabilitating the term ‘outlaw.’ It was the name of a compilation record, but it was really about artistic freedom. That’s what it’s about.”

Earle should know. While on the verge of dropping out of high school, Doug Sahm moved into Earle’s neighborhood. Earle watched the storied icon behind “She’s About a Mover” tell Atlantic Records’ Jerry Wexler to sign Willie Nelson, who was back in Texas decompressing from Music City’s Music Row machine. That conversation resulted in the groundbreaking Shotgun Willie and Phases and Stages. Earle was at Nelson’s first Dripping Springs Reunion, the precursor to the legendary Fourth of July Picnics, where “everybody was kinda eyeballing each other. It was a big failure—maybe that’s what everybody forgets. But it was Tom T. Hall, Charlie Rich— right as ‘Behind Closed Doors’ was breaking—Willie, Waylon. Johnny Bush was there.”

Long before “outlaw” was a charged marketing term, it was being defined by flops and fiascos. Earle—a kid who bailed on high school to keep from getting beaten up by rednecks—was finding his place in the crowd of erstwhile writers, pickers and outliers. Fluent in the ways of rural kids, cowboys and hippie-fringe types who flaunted convention, ultimately, it was the music that set his course.

“My heroes were The Beatles and the Stones and John Sebastian for a period of time in the 9TH grade,” he explains. “And then, all of a sudden, I found there were these people that were closer to me. I knew a lot about Townes Van Zandt; I heard about him. I never saw him play because [Townes] never came to San Antonio. You know, I sort of had a bad case of Jerry Jeff Walker worship for a moment.”

Between the local Texas songwriters, KOKE, the progressive country station and Houston’s Pacifica Radio outlet, the seeds were sown. There was a rift happening in Texas—one defined in part by music.

Earle laughs at his brashness. “I crashed Jerry Jeff’s 33rd birthday party. I heard it was way out on North Lamar. I’d hitchhiked there, so I didn’t have a car. I was talking this girl into driving out there. I told her we were invited. I sorta imagined Jerry Jeff had just spotted me, and was about to throw me out, when Townes came crashing through the door and got everybody’s attention, and saved me…”

There’s almost a pause. Earle, who’s working on his memoir, recognizes the gap between hard facts and reality. Half a beat has passed. “Well, that’s the way I remember it. I’m not sure if it’s true.”

It would be another three months before Townes Van Zandt would heckle the longhaired young man during a set at the iconic Old Quarter with requests for “Wabash Cannonball.” Earle, never one to flinch or back down, had another idea: a spot-on version of TVZ’s very complex “Mr. Mudd and Mr. Gold.”

A friendship began—one that sustained Earle through a tentative move to Music City, an extended period of running into walls professionally and the introduction to Guy Clark, as well as fellow young buck Rodney Crowell. Heartworn Highways, the recently resurfaced documentary about the Texas/roots fringe in ‘70s Nashville, shows a kid, ambitious, cocky, straining to get his hands on the dream. Just as important, it reveals a songwriter smart enough to maintain some semblance of cool to keep his place in this court of top-shelf songwriters who were shaping the careers of Waylon Jennings, Willie Nelson, Emmylou Harris and Johnny Cash.

When Earle arrived in ‘74, Clark deemed country as “one long commercial for CB radios.” It was in the wake of Urban Cowboy, and on the surface things were bleak. But below the surface, the Outlaws were becoming their own kind of country. And the long drawling youth leaned into that ethos.

“I’m a post-Bob Dylan songwriter. My whole generation is and we were doing it on purpose. Kris [Kristofferson] is a post-Dylan songwriter, and he knew that kind of poetry would work in country music. [Mickey] Newbury made Kris believe [he could do it], and we all, Townes, Guy, me, believed because of Kris. Kris Kristofferson has a lot to do with all of us being here.” That merging of moments and hard truths, tough decisions and rough realizations has tempered his songwriting. From the bleary-eyed kid in the allnight quick-stop of Guitar Town’s “Someday” to the third-generation contrabander growing dope in “Copperhead Road,” and from the lobbyists killing time in “Christmas in Washington” to the disheveled, disaffected young Americans fighting for the Taliban in “John Walker’s Blues,” Earle has sought the details that defined his characters from the inside out—and offered insight into how the outsiders and those left behind feel.

In a world where the personal is political, Earle’s politics have often been out front. An aggressive opponent of the death penalty and supporter of pro-choice rights, he’s been a host on the now-defunct, liberal talkradio network Air America. Though the election of Donald Trump—which he referred to with a flat “This is for Dickhead,” while introducing “City of Immigrants” during his SiriusXM Outlaw Country broadcast—would seem to call for an overtly political record, Earle drew on the politics of his own life.

Beyond the co-opting of the term “outlaw,” the 62-year-old songwriter is once again facing single life. Having finalized his divorce from singer-songwriter Allison Moorer, Earle is learning the tides of a life on his own—that is as “on his own” as a touring musician, who acts and writes, can be.

“My politics are born completely and totally of romance,” Earle begins. “What I hate about the Republicans more than anything is their pragmatism. Capitalism exists; it’s a force of nature, not an ideology. Mistaking it for that is being too fucking lazy to form an ideology. It’s like people confuse romance and sex. Romance is about things being the way they should be, and the refusal to accept things the way they are. We made this record in December, and I thought Hillary Clinton— not my choice, but the better of the two—was going to be president when I was writing and I thought maybe I needed to go write some political songs, but these songs go together. And sometimes you do that; I figure I’ve earned the right. These last two records are a lot about my divorce, adjusting to being alone. To me, if you’re not exposing yourself, you’re probably wasting your time. You’re not completely with me if you’re not letting some of yourself go. You can’t be afraid of it, or it isn’t art.”

Whether it’s the descending churn of “Lookin’ for a Woman,” the twin-fiddle basted Texas dance hall of “You Broke My Heart” or the jangle-pop country duet with Miranda Lambert “This Is How It Ends,” the dashed hopes and jagged feelings drive many of the songs. There’s also a healthy dose of ne’er-do-well brio in the sweeping “If Mama Coulda Seen Me,” the lumbering churn of “Fixin’ to Die” and the finger-picking showcase “News From Colorado,” which offer festering moments of life rubbed raw.

“The job is empathy. It really is,” Earle allows as the interview winds down. “There’s that commitment to art…and it’s why the best country songs are being written by women. Brandy Clark, Kacey Musgraves, Miranda Lambert. A lot of artists have their names on songs they didn’t write; they sit in a room and take half the song.”

Earle shifts his weight and leans forward. He’s talked about New York City being good for him, knowing the homeless guy who lives in the next doorway, and his ability to pick up single tickets to ball games and Broadway shows. If he didn’t think he’d end up on his own, then he’s aware—as the song declares—“livin’ on the road ain’t all it’s cracked up to be.”

Strip away the romance, and there’s not much left. Conceding, “I’m not lonely, ‘til I am,” Earle weighs the wages of being gone. “Commiting to art at the level I have costs something. Most people couldn’t spend the amount of time on a bus that I do, or pay what I pay for it. I’m being punished again for the fact that I make my living being gone. It gets used against you in court. It gets used against you because girls want to make you feel guilty; it gets used against you because kids want to make you feel guilty. You feel guilty, and you are guilty.”

Earle hesitates, then, draws the larger circle of life captured by art. If his son Justin Townes Earle has spent time decrying his father’s absence, then the Americana artist is now having to grapple with the same choices his father faced.

“Justin’s getting ready to be a dad, and we’ve been talking about this a lot,” Earle says of his oldest son. “He’s getting ready to find out. Maybe he’ll make a different choice than I did. I was never running from anything; I’m pretty domesticated.”