Steve Earle’s got some stories. You don’t pal around with Townes Van Zandt, sustain a 30-year career in music, survive a devastating heroin addiction, serve hard time, and collect six ex-wives without gaining a few good tales to tell.

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Earle’s mistakes, excesses, and fuckups shaped the three-time Grammy winner into one of the most respected living American songwriters. He’s also an accomplished actor, author, playwright, and political activist, often aligning with progressive politics.

For his new album, however, Earle returns to what he’s always done best: swaggering country-rock and story-driven ballads. So You Wannabe an Outlaw? got its start after Earle was asked to contribute two songs to the TV drama Nashville. One of those tracks, “If Mama Coulda Seen Me,” was used for the show; the other, “Lookin’ for a Woman,” was not. While on tour with Shawn Colvin last year, Earle looked at these two songs and had an epiphany.

“I get on the road, and I gotta start thinking about what my next record is gonna be,” Earle says before a recent in-store performance at Music Millennium. “And I realize I had these two songs, and they sorta have this vibe. And I was trying to figure out what it was, to connect them, and then I realized I’d been listening to Honky Tonk Heroes.”

Honky Tonk Heroes, the 1973 album by Waylon Jennings, is associated with the rise of “outlaw country”—a term that’s often used to describe to the work of Willie Nelson, Kris Kristofferson, and Jerry Jeff Walker, among others. With their hard-and-fast lifestyles and noncompliance with whatever rules apply to professional musicians, Jennings (who died in 2002) and Earle might be considered close kin. For his new album, Earle decided to pay homage to Jennings’ outlaw spirit.

“I just kinda went with that,” he says, “and decided to unapologetically channel Waylon Jennings, to the best of my ability, for the whole record.”

To approximate Jennings’ signature guitar sound, Earle played on the back pickup of a 1955 Telecaster guitar. About half the songs on the record, including “If Mama Coulda Seen Me,” “Firebreak Line,” and the title track (with guest vocals by Willie Nelson) are full-throttle country scorchers, rivaling anything Jennings ever recorded. The other songs, especially “You Broke My Heart” and “This is How It Ends” (co-written with and guest vocals by Miranda Lambert), are slower, sadder country ballads inspired by his recent divorce from singer/songwriter Allison Moorer.

“Being left is different than leaving somebody,” he explains. “I’ve done that, too, and that has its own set of guilt and baggage. But being left is being rejected, and it’s hard. There’s been country songs about that for a long time.”

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With So You Wannabe an Outlaw? Earle continues the long tradition of country songs about heartbreak and hell-raising. Though the exploits of the honky-tonk heroes of yore have reached legendary (and sometimes hyperbolic) status, Earle is quick to point out that they earned their outlaw reputations more in the boardroom than in the barroom. After all, country singers behaving badly didn’t begin with Waylon and Willie.

“A journalist in Australia on the phone the other night said, ‘Wasn’t it really about your lifestyle, the stuff that you were doing?’ No, it wasn’t,” Earle says. “Look, George Jones was not going to the liquor store at 3:30 in the morning on a lawnmower. There aren’t any liquor stores open in Tennessee at 3:30 in the morning. He’s going someplace else. The first person I ever heard of freebasing in Nashville was George Jones. Country artists did those things. It just didn’t get talked about. What it was about was artistic freedom. That’s why people called them outlaws, because they didn’t do what they were told.” recommended