6 of the Best Outlaw Country Songs for the True Rebellious Cowboy

The 1970s was the golden era of outlaw country, and a lot of amazing music came out during that time. Known for its no-rules attitude and lack of interest in appealing the mainstream country fans, outlaw country celebrated the cowboy ethos and produced some real movers and shakers in the country music world, from Waylon Jennings to Willie Nelson to Merle Haggard. Let’s take a look at six outlaw country songs that are essential listening for any old-school rebel. Some of these tunes are classics you’ve likely heard before, while a few others are on the obscure side.

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1. “London Homesick Blues” by Jerry Jeff Walker

A bit on the underrated side, “London Homesick Blues” by Jerry Jeff Walker is an unabashed outlaw country tune about a Texan stuck in London, England. It’s a painfully homesick tune that a lot of listeners could relate to.

2. “Copperhead Road” by Steve Earle

“Copperhead Road” by Steve Earle came out in the late 1980s and proved that outlaw country music was far from dead. Earle tells the tale of a Vietnam War vet who decides to grow pot instead of jumping on the family business of bootlegging. 

3. “Folsom Prison Blues” by Johnny Cash

One of the most easily recognizable outlaw country songs out there, you just can’t beat the sweaty, powerful energy of “Folsom Prison Blues” by Johnny Cash. Cash was performing for prisoners and giving a stiff middle finger to the status quo when it wasn’t yet cool to do so. In a way, Cash is one of the most punk-rock musicians of his time, but his music is pure outlaw country either way.

4. “Red Headed Stranger” by Willie Nelson

This is the outlaw country song of outlaw country songs. “Red Headed Stranger” by Willie Nelson set the mood for the early beginnings of the genre, and it marked the first time in Nelson’s career in which he had full creative control over his work. The resulting concept album of the same name is still the stuff of legend today.

5. “I’m Not Lisa” by Jessi Colter

This is a really underrated one. “I’m Not Lisa” by Jessi Colter is on the obscure side of outlaw country, but it’s an outlaw country bop nonetheless. It also happened to be Jessi Colter’s first major hit as a solo musician outside of her collaborations with her late husband, Waylon Jennings.

6. “Don’t You Think This Outlaw Bit’s Done Got Out Of Hand?” by Waylon Jennings

Waylon Jennings produced virtually endless outlaw country songs in his heyday, and any of those tunes could make this list. I went with “Don’t You Think This Outlaw Bit’s Done Got Out Of Hand?” simply based on how self-referential it is. This one’s a bona fide anthem if there ever was one.

Photo by David Redfern/Redferns

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