10 Essential Outlaw Country Albums

Johnny Cash wasn’t the first country outlaw, but he pounded that maverick mindset into the firmament of country music more indelibly than anybody before him. And one of the biggest nails he hammered was recorded live at Folsom State Prison in 1968. Cash had played for convicts at other institutions before, but at this epochal event his Man in Black persona, the desperado-type tunes he chose, and the hard reality of the setting all dovetailed to create a major moment in American culture.

He’d already had a big hit with his original recording of “Folsom Prison Blues” more than a decade earlier; but when he performed the jailhouse lament in the place that inspired it, for the people who’d lived it, it gained exponentially greater impact.

It was Johnny Cash who expedited Kris Kristofferson’s path to fame by cutting his morning-after-excess anthem “Sunday Mornin’ Comin’ Down” in 1970. And it was Kristofferson.

Some of the songs had already been covered by highly placed irers like Cash, but the sound of Kristofferson tearing into tunes about “getting by high and strange,” to quote one of his later songs, gave iconoclasts in and outside of the country world license to start busting through boundaries.

Willie Nelson had been struggling for country stardom since the late ‘50s, scoring a couple of hits but ultimately earning his biggest success writing chart-toppers for others (Faron Young’s “Hello Walls,” etc.). By the early ‘70s, Willie was tired of playing the Nashville game. He decided to see what happened if he started letting it all hang out in every sense, growing his hair like the hippie types with whom he’d found common ground, and pursuing a sound informed by soul, blues, folk, Western swing, and whatever else floated his boat.

When he shifted over to Shotgun Willie.

There must have been something in the air back in June of ‘73. Just two weeks after the arrival of Shotgun Willie, Waylon Jennings completed the one-two punch with Honky Tonk Heroes. Like his pal and fellow Texan Willie, Waylon had already been hanging out his shingle for about a decade and a half. He’d found more commercial success than Nelson but was similarly straining against the chains of impersonal Nashville-ian production.

Billy Joe Shaver enabled Waylon to perfect his independent vision. With nine of its 10 tracks written by Shaver, Honky Tonk Heroes came crashing through the gate with a rough ‘n’ ready sound rawer than anything to emerge from the country sphere in years. Between them, HTH and Shotgun Willie incited a revolution.

Billy Joe Shaver emerged out of nowhere to become the poet laureate of the mid ‘70s Outlaw Country boom. Yet another Texan, he was the wildest of the pack, the embodiment of the outlaw ideal to a fault. When Waylon Jennings filled his game-changing Honky Tonk Heroes with Shaver songs, Billy Joe earned some of the spotlight for himself and became a recording artist.

Shaver’s Kris Kristofferson-produced 1973 debut LP, Old Five and Dimers Like Me, featured his own versions of a few of the tunes Waylon had cut, but it left room to reveal there were plenty more where those came from. Bursting with character, he sounded like the soused sidekick from some vintage Western, and his lyrics threaded the needle of poetry with a hardscrabble, homegrown vibe that made them instant classics.

Sings Lullabys, Legends And Lies is a double album penned by the man who became known as Outlaw Country’s irreverent class clown (he’d already written the gloriously goofy Johnny Cash smash “A Boy Named Sue.”) With a tall-tales theme and a production style as freewheeling as the songs themselves, it set Bare in an entirely different direction, where he’d have Silverstein by his side for plenty more albums to come.

In the late ‘60s/early ‘70s, the success of forward-thinking folks like Kris Kristofferson and Old No. 1.

Like his buddy Townes, Clark brought a coffeehouse troubadour touch to his country/folk concoctions. But his brand of expertly forged songpoetry was defined by hard-bitten imagery from the Western plains, not ethereal flights of fancy. And his early albums were the inspirational springboard for a whole other branch of outside-the-box country artists, including Rodney Crowell, and loads more. 

Opinion about the production on Townes Van Zandt’s early albums varies. But almost everybody seems to agree that Live At The Old Quarter is the purest, most potent Townes experience available. Recorded in 1973 but not released till ‘77, it’s the longhorn poet unplugged and alone in front of a small but hearty audience, plowing through a double album’s worth of his most powerful tunes, from the elliptical imagery of “Two Girls” to the naked emotion of “If I Needed You” and the transcendent balladry of “Rex’s Blues.”

Since TVZ’s 1997 ing, his legend has grown to the degree that a venue as cozy as the Old Quarter could never contain his audience today.

When Guy Clark hosted now-legendary song swap sessions at his Nashville home in the ‘70s, one of the regulars was a promising young buck by the name of Steve Earle, who soaked up as much of Clark’s storytelling prowess as possible. By the 1980s, Earle was all grown up and busting out in a big way.

His ‘86 debut album, Guitar Town, placed him at the forefront of what people would come to call alt country, which was more or less the next generation’s way of saying “outlaw.” Right from the start, Earle had the guts of a rocker, the heart of a balladeer, and the soul of a country singer, and he made it all count. In his own way, he’d end up being nearly as influential as his heroes, and Guitar Town is what got his story started.

Gen X got its own Outlaw Country hero when That Lonesome Song.

Clearly schooled in the verities of Waylon and Willie, but still sporting a set of unique musical fingerprints, he deftly deployed his cavernous, gravitas-laden voice on songs that weren’t afraid to take a hard look at the dark side of things. In an era when raw, rootsy renegades were in short supply in Nashville, That Lonesome Song served notice that the Outlaw spirit was still living loud and proud.