Outlaw country is a movement of music by and for American rebels who embrace their true desires. For some, that’s expressing their desire to be free, often in highly politicized terms; for others, it’s just about showing off their inner dirtbag.
This underground, anti-authoritarian strain of country began in the 1960s as a rebellion against the factory system of formulaic songwriting forced onto artists in Nashville, the epicenter of country music. These nonconformists wanted to write their own music, play with whomever they wanted, and control the rights to their songs.
The hotbed of the original outlaw scene was Texas, where the music became the aural personification of the Lone Star State and its exceptional sense of exceptionalism. Willie Nelson, Kris Kristofferson and Waylon Jennings are often cited as critical adopters of this outlaw ethos, and many others followed suit. Since then, there have been several waves of the style, and even though the term “outlaw country” has been so broadly applied over the past 40 years — most recently, to artists like Chris Stapleton, Kacey Musgraves, Aaron Lewis and even Kid Rock — that it doesn’t really mean much anymore, for the artists on this list, it has meant everything.
For this list, the usual caveats apply: This is not comprehensive or necessarily the “best” but, rather, a primer for the uninformed. We stuck to stuff pre-1980s, before a new wave of singers like Robert Earl Keen, Cory Morrow and Pat Green came along. But feel free to share your favorite deep cuts in the comments.
10. “Family Tradition” – Hank Williams, Jr. (1979)
Hank Jr. is the middleman in an important country lineage. Though he’s essentially become the country version of Ted Nugent with his xenophobic, predictably racist tirades, he made some hits in his day, including this sing-along about getting lifted as being an old family tradition. A staple in old Southern barrooms to this day.
9. Charlie Daniels – “Uneasy Rider” (1973)
Charlie Daniels ended up espousing a puzzling mixture of neocon and libertarian sentiments in his later years, but this tune from 1973 is a curious tale where the protagonist is the pot-smoking hippie who gets trapped in the Deep South and has to hightail it out of there to make it to the progressive West Coast. Followed by a sequel, the equally transgressive “Uneasy Rider ‘88.”
8. Johnny Paycheck – “Take This Job And Shove It” (1977)
Written and originally recorded by David Allan Coe, Johnny Paycheck made this one a hit in 1977. There’s truth in advertising with Mr. Paycheck, because Johnny Paycheck is the type of dude who looks like a guy whose name is Johnny Paycheck. It was such a hit that it inspired a movie of the same name. Three guesses what this tune is about, and the first two don’t count.
7. Johnny Cash – “Cocaine Blues” (1968)
JC is a godfather of outlaw country and the most mythologized of this gang, though some would argue he didn’t go full-blown outlaw until the ‘70s when the mainstream lost interest. Still, his version of “Cocaine Blues” (a song that actually dates back to 1947) is a giant eff-you to basically all societal constructs and rules, especially since he played it to a bunch of prisoners in his notorious Folsom Prison concert to get them turnt. He even met with Nixon to try to get him to reform our criminal justice system, which at the time was about as progressive as anyone in country music ever got.
6. Jerry Jeff Walker – “Mr. Bojangles” (1968)
Walker got the inspiration for this tune in a New Orleans jail cell, where he met a homeless tap dancer who went by Bojangles, the nickname of famed dancer Bill Robinson. Though written before the true outlaw country boom really got cooking, this song shows the softer, more elegiac side of outlaw and deserves to be in the Great American Songbook.
5. Tanya Tucker – “Texas (When I Die)” (1978)
Outlaw country was mostly a boys’ club. But Tanya Tucker was a young singer-songwriter who quickly became a star as she pushed her outlaw image with songs like “Texas (When I Die).” The song’s lyrics are pretty straightforward: When she dies, she wants to go to Texas, because heaven probably doesn’t let cowboys in. Tucker hasn’t had to find the intricacies of heaven’s door policy just yet, as she’s still going strong today.
4. Townes Van Zandt – “Pancho and Lefty” (1972)
Townes Van Zandt was a kid from an elite background who received shock therapy as a child to treat his bipolar disorder, which likely only made things worse. As an adult, he mostly lived in some form of poverty or another, with rumors circulating that he lived in a shack with no electricity for a while. His addiction issues were tragic. He had it so bad that at one point he moved on from shooting up coke and heroin to injecting cocktails of rum and coke. The enigmatic Van Zandt has become one of country's most celebrated singer-songwriters since his death in 1997, and “Pancho and Lefty” remains one of his most enduring tunes.
3. Kris Kristofferson – “Gettin’ By, High and Strange” (1972)
Kris Kristofferson is an all-time great songwriter and one of the indispensable outlaw country figures, not to mention an accomplished actor (Blade, anyone?). “Gettin’ By, High and Strange” is one of his signature takes on man-as-tumbleweed, going along with the flow and getting stoned to help get him through the journey and the day. Kristofferson, Cash, Jennings and Nelson would later form the supergroup The Highwaymen and record three solid LPs in the ‘80s and '90s.
2. Merle Haggard – “Okie From Muskogee” (1969)
Haggard’s “Okie From Muskogee” is one of the most puzzling country songs of all time. Taken at face value, it’s an anti-hippie anthem, decrying the anti-Vietnam movement and marijuana use. However, it ended up being re-appropriated by the counterculture as a pro-hippie and pro-weed anthem. Haggard issued many contradictory statements over the years about what the song means and what he felt about the counterculture at the time, though he eventually came around to recognize that the vilification of marijuana was pure propaganda. He later came to the Dixie Chicks’ aid when they were destroyed by the far right media for protesting Iraq. So, Haggard and his politics were complex, to say the least.
1. Waylon Jennings and Willie Nelson – “Mammas Don’t Let Your Babies Grow Up to Be Cowboys” (1978)
You could fill several books with the tales of Jennings and Nelson, as they represent the heart and soul of outlaw country and over 100 combined years of making music. Jennings was all over pop culture history, from being the narrator in The Dukes of Hazzard to famously giving up his seat on the airplane that crashed with Ritchie Valens and Buddy Holly, and Nelson is a living legend, most famously associated by a younger generation with weed. Taken from their album of duets, Waylon and Willie, Jennings and Nelson covered Ed Bruce’s “Mommas Don’t Let Your Babies Grow Up to be Cowboys” — a simple song, beautifully executed — and elevated it to a no-brainer addition to the country canon.