10 Classic Outlaw Country Jams for People Who Don't Know Shit About Outlaw Country

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.

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