5 Most “On’ry” Rebels of Outlaw Country

If not for the dominance of the Nashville Sound in country music during the 1960s, there might not have been such a thing as outlaw country. As mainstream country became more polished and formulaic during that decade, some artists pushed back against the pressure to record songs that would fit the commercial mold. Over time, the music that resulted from this resistance would come to be known as “outlaw country.”

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The music itself bore certain characteristics. Instead of incorporating the hallmarks of the Nashville Sound, such as string arrangements and vocal harmonies, it harkened back to older country styles, such as honky-tonk and rockabilly, and eschewed an emphasis on sophisticated production techniques. Outlaw country also incorporated rock elements and dealt with lyrical themes that were unpalatable to the mainstream, such as drug use and life on the road.

The following five musicians and songwriters were a key part of the music and history of outlaw country, and have left an indelible mark on the genre.

1. Waylon Jennings

There is not a clear consensus on who is responsible for the creation of the outlaw country sub-genre, but Waylon Jennings is as good as anyone to be credited with that achievement. His rebellion against the country music establishment was more than just about his style of music or dress. He negotiated a deal with RCA Victor in which he could produce his own records and make them at the studio of his choice. It’s hard to imagine that his 1973 album, Honky Tonk Heroes, would have had the same lo-fi charm if left in the hands of a producer chosen by the label.

2. Billy Joe Shaver

If Jennings is a central figure in outlaw country, then Honky Tonk Heroes was a seminal album, and Billy Joe Shaver’s fingerprints were all over it. He wrote or co-wrote all but one of the album’s 10 tracks and worked with Jennings (sometimes contentiously) on the arrangements. Shaver’s own album, Old Five and Dimers Like Me, is also an important part of the outlaw country canon; his songs were recorded by artists such as Elvis Presley, Kris Kristofferson, Johnny Cash, and Bob Dylan.

3. Jessi Colter

The outlaw country movement was male-dominated, but Colter scored one of the biggest hits to come out of the sub-genre, when she took “I’m Not Lisa” to No. 1 on the Billboard Country Chart and No. 4 on the Billboard pop chart. She also hit the Billboard Country Top 40 twice in 1970 with duets with Jennings (as “Waylon & Jessi”), whom she’d married in 1969. Then in 1976, Colter was featured on Wanted! The Outlaws with Jennings, Willie Nelson, and Tompall Glaser; it became the first country album to sell over 1 million copies.

4. Willie Nelson

By the time Nelson moved from Nashville to Austin to start a new chapter in his career, he had already released 15 studio albums and written hit songs recorded by other artists, most notably “Crazy” by Patsy Cline. The first album Nelson made after moving to Austin was 1973’s Shotgun Willie, which was also his first release for Atlantic Records. It represented a change in direction for Nelson, and by the time he got to 1975’s Red Headed Stranger—a concept album about a preacher who murders his wife and her lover—the instrumentation was whittled down to mostly just guitar, bass, vocals and a minimal layer of drums. By the late ‘70s, outlaw country was no longer in vogue, but Nelson’s career only got bigger in the ‘80s with the crossover hits “On the Road Again,” “Always on My Mind” and “To All the Girls I’ve Loved Before” (with Julio Iglesias).

5. Kris Kristofferson

Kristofferson may be better known for his acting career and for the songs he wrote for other artists, most notably “Me and Bobby McGee” and “Sunday Mornin’ Comin’ Down.” However, his own recordings in the early ‘70s, such as Border Lord and Jesus Was a Capricorn, fit in thematically with the albums being made by Jennings and Nelson. In the ‘80s and ‘90s, Kristofferson was a member of the outlaw country supergroup The Highwaymen along with Jennings, Nelson, and Cash.

Photo by Rob Verhorst/Redferns

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  1. Well, I’m glad to se Kristofferson given his due, because his songs came along and started the ball rolling even before Jennings broke the recording system and Willie dumped his short hair and turtleneck shirt image. He’s the best darned songwriter who ever lived.

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