The rules of being a country music star used to be simple: you sing the songs the label picks for you, you show up to sing at the Opry when the label tells you to, and you’ll be off on a nice little singing career. This factory-esque system flourished — with a couple of Hank Williams and Johnny Cash shaped exceptions — from the first time a poor southerner with mandolin skills walked into a recording booth.
But rock music, particularly the Beatles and Dylan, had showed a generation of performers in every genre that it was possible to choose what you sing, and furthermore, be the one who writes it. You could be a star by following your own gut and doing what you wanted to do not only in the bars of Nashville, but in the recording studio too.
That’s how outlaw country was born; a whole wave of young stars — who liked the weed those hippies from the coasts were smoking — decided to take agency over their own careers and make the music they wanted to make, some of them even in a major label system. The genre title wasn’t clever: a lot of the songs were about how they saw themselves as outlaws, smoking dope and pillaging the American south on their tours.
Despite all odds, outlaw country has become an ensconced genre conceit in country music. Anytime a country singer does an album that doesn’t sound like mainstream country, it gets labeled as outlaw country. That doesn’t mean that it’s not outlaw country; it’s just hard to imagine Waylon Jennings trying to make an album that sounds like 1933 in 1973 like the people labeled outlaw country in 2016 are making albums that sound like 1976. That said, there are some modern albums that ascend the outlaw country throne. Doing what you consider to be “true” is the only hallmark of a good outlaw country album, and these 10 are the most true.
An accomplished songwriter before he ever started a solo career—he wrote “Me and Bobby McGee” for Janis Joplin, and famously landed a helicopter in Johnny Cash’s front yard in a bid to get Johnny to record some of his songs, which he eventually did — Kristofferson’s first five projects for the Monument label are all classics. He might have been the first alt-country singer — along with the next entry in this list — since he made undeniably country music that was always left of center from whatever was happening in the genre at large. His biggest hit album is Jesus Was a Capricorn, an album with ruminations on faith, Jesse James, and love, in the duets with his soon-to-be wife Rita Coolidge. Jesus hit number one on the country charts, laying a lot of runway for songwriters like Willie Nelson — who was still trying to break through as a solo performer — and for musicians ready to let their inner weirdo flourish (see: Jennings, Waylon).
Townes himself would have probably bristled at being lumped in with any of the artists here, but dude deserves some outlaw cred: He stayed outside of the machinations of Nashville his whole career, probably to his detriment — he never made enough money/got clean enough to not live in basically a shack — and only made the music he wanted to make. The Late Great is his crowning achievement; it’s got testaments to his master-class songwriting like “Pancho & Lefty” and “If I Needed You.”
Find out where it all began for Townes Van Zandt by signing up here for Vinyl Me, Please Essentials to receive the 50th-anniversary edition of his first album, 'For the Sake of the Song.'
If there’s a platonic ideal of an outlaw country album, this is probably it. It’s 10 songs — mostly written by country outlaw Billy Joe Shaver — about trying to romance women out of saloons, the misery and weariness of the roaming life, and hanging out in Mexico for no reason at all. Jennings famously had to fight his label to get them to release this, but then it was a hit among non-country audiences — it famously got a rave review in Rolling Stone — and launched Jennings into a more meaningful career than he was set up to have. He opened the gates for all the major label outlaws coming behind him.
After some years pumping out songs that were more famous for other people, Willie Nelson decamped to Columbia Records — home of Bob Dylan — in the early '70s, where they were foolhardy enough to give him full creative control. He responded with the best albums of his career: Red Headed Stranger, a sparsely produced concept album based on a song he used to play on his old radio show, is one of the best of those. Nobody writes better love songs than Willie, and this one has a couple doozies, particularly “Can I Sleep In Your Arms.” Outlaws need love too.
Unfortunately, outlaw country mostly meant liberation for male performers; women were still mostly stuck in the record-what-we-want structure of major label country if they weren’t named Loretta or Dolly or Tammy. However, outlaw country’s ethos did extend to some women; Jessi Colter — wife of Waylon, mother of Shooter — made a couple albums in the mid-'70s that fit under the genre, the best one being I’m Jessi Colter, an album Colter wrote on her own with production help from Waylon. The album spawned her biggest solo hit — the biting “I’m Not Lisa,” a song about how her lover has to get over his ex, because she ain’t her. Colter gets backgrounded unfairly in the story of outlaw and alt country; without her mid-'70s work, it’s hard to imagine a world ready for Lucinda Williams or Brandy Clark.
Putting a compilation album here is probably cheating, but this album had more to do with solidifying the players, the sound, and the aesthetics of outlaw country. Featuring songs from Waylon, Willie, Jessi and Tompall Glaser — Jennings’ producer, and an outlaw performer with Tompall & The Glaser Brothers — Wanted! was the first country album to ever be certified platinum, as people from around the country, some of them who had never purchased a country album, bought into the outlaw imagery and total package. It’s essential, but Waylon and Jessi’s cover of “Suspicious Minds” make it a must own.
Tanya Tucker was one of the biggest stars in mainstream country by the time she started recording her ninth album, TNT. Instead of shooting for the middle-of-the-road country that made her a household name, she basically went full rock on TNT; this thing has more in common with a Joan Jett album than a Loretta Lynn album. But it also sounds like outlaw country, in that Tucker sounds like she’s taking the reigns of her career, and making the shit-kicking album she wanted to make. “Texas (When I Die)” should replace whatever song is currently the song of Texas.
Sure, Johnny made some badass albums in the '60s — his series recorded at prisons in California for instance — but I would contend he didn’t truly stop caring and go full outlaw till he started the American Recordings. He had nothing left to lose; his career was flatlining, and his voice was slower and on the verge of breaking, and then he hit the studio with Rick Rubin for the first of the American albums and he spent the last decade of his career as famous as he was in the '60s. The albums feel like an outlaw writing his own Tombstone.
Some of us choose the outlaw country, others are born into it. There was no chance Shooter wasn’t going to make a debut album that sounds like it came out between albums during his dad’s '70s run. Put the O, produced by super producer Dave Cobb before he was super producer Dave Cobb, spawned the biggest hit of Shooter’s career — “4th of July” — which he’s basically spent the last 11 years dodging, because real outlaws avoid labels at all costs. His album from this year — the Giorgio Moroder covers album Countach — is also an outlaw country classic.
A lot of the time, when modern acts shoot for that outlaw aesthetic, it’s naked and you can totally see it coming. You don’t make Midwest Farmer’s Daughter or Traveller without wanting to be compared to Waylon, Jessi or Willie. And while Jamey Johnson is clearly fishing for those same comparisons, his The Guitar Song is doing so in overkill: It’s a double album (!) with two halves (Black and White side) that tell a story of ultimate redemption. There are too many great songs on here to list; if you’re not sold after “Can’t Cash My Checks” I don’t know what to tell you. The vinyl edition is incredible; the albums split in the middle of three discs, so there’s a black, white and black and white disc in the set. The message is clear: If you’re gonna go outlaw as a modern performer, it’s no half measure. You have to commit 100 percent.
If you like outlaw country, you’ll love this: Vinyl Me, Please is reissuing Townes Van Zandt’s debut LP, For The Sake Of The Song for its 50th anniversary. On midnight blue vinyl, it comes with brand new liner notes. You can subscribe here.
Andrew Winistorfer is Vinyl Me, Please’s Classics and Country Director, and an editor of their books, 100 Albums You Need In Your Collection and The Best Record Stores In The United States. He’s written Listening Notes for more than 20 VMP releases, and co-produced Nat Turner Rebellion's Laugh to Keep From Crying. He lives in Saint Paul, Minnesota.