4 Outlaw Country Songs for Beginners

The country music rebels of the 1970s had grown tired of Nashville’s establishment.

Though they weren’t the only ones, four renegade musicians transformed country music. Known as The Highwaymen, Kris Kristofferson, Waylon Jennings, Johnny Cash, and Willie Nelson—collectively and individually—embodied what became known as outlaw country.

They bucked the Nashville record business and restored rawness and authenticity to a genre that had given in to smooth edges and pop sheen.

Before its time as a cheap marketing slogan and subsequent resurgence, “outlaw” was an organic countercultural movement. For a deeper dive into the history, check out Brian Fairbanks’ book Willie, Waylon, and the Boys: How Nashville Outsiders Changed Country Music Forever.

Here’s a beginner’s guide to four outlaw country classics.  

The red-headed stranger had eyes like thunder
And his lips, they were sad and tight.

“Me and Bobby McGee” by Kris Kristofferson from Kristofferson (1970)

The late Kris Kristofferson’s outlaw classic was made famous by Roger Miller, Gordon Lightfoot, and Janis Joplin. Months after Joplin’s death in 1970, her version topped the Billboard Hot 100. But Kristofferson’s own version arrived on his 1970 debut album Kristofferson. There’s a long-running debate over what is and isn’t country music. Real country music. But Kristofferson opens “Me and Bobby McGee” by saying, “If it sounds country, man, that’s what it is. It’s a country song.” His ragged version is everything one wants from a country tune: a worn voice, slightly off-kilter, singing plainly and emotionally about everyday hardships.

“Highwayman” by The Highwaymen from Highwayman (1985)

“Highwayman” is the gold standard for a timeless country tune. On their debut as The Highwaymen, Kris Kristofferson, Johnny Cash, Waylon Jennings, and Willie Nelson carried the outlaw torch into the next decade, and beyond. Jimmy Webb wrote “Highwayman” after a long night of “professional drinking” with Harry Nilsson. Then the song arrived in a dream and Webb recorded his version in 1977. Glen Campbell recorded the song in 1979 before it became the inspiration for an outlaw supergroup.  

“Are You Sure Hank Done It This Way” by Waylon Jennings from Dreaming My Dreams (1975)

If you are an outlaw country artist or aspire to be one, you can begin by asking a simple question: What would Hank Williams do? Looking at the state of country music—from Hank to the gleaming polish of the “Nashville sound”—Waylon Jennings, with his signature phased guitar sound, used two chords to reject Nashville’s orchestrated blandness. Jennings objected to the rhinestone suits, shiny cars, and commercial glitz of ’70s country stars. It’s an outlaw declaration: Lord, it’s the same old tune, fiddle, and guitar / Where do we take it from here?

“Blue Eyes Crying in the Rain” by Willie Nelson from Red Headed Stranger (1975)

Upon hearing Red Headed Stranger, Columbia Records thought Willie Nelson had submitted something unfinished. Waylon Jennings accompanied Nelson’s manager to play the album for Columbia president Bruce Lundvall, who suggested the album required further production. Infuriated, Jennings shouted, “That’s what Willie’s all about. He doesn’t need a producer.” The album is important as a real-time protest against Nashville’s homogenization of country music. To Lundvall’s credit, he soon fell in love with the album. “Blues Eyes Crying in the Rain” became Nelson’s first No. 1 hit as an artist. However, Nelson didn’t plan the revolution. He just noticed that his audience liked “the real simple three-chord country stuff.”

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