Waylon Jennings died in 2002 but his legacy and deep discography live on. His music and attitude still inspire countless listeners and artists and will likely continue to do so for years to come. His is the story of a talented singer/songwriter who played by Nashville’s rules until he found them too restrictive. His rebellion against the industry machine led him to become one of the originators of the Outlaw Country movement.
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In recent years, many country music fans have found themselves digging into icons from the genre’s history in search of something different and authentic. When it comes to country music, it doesn’t get much more authentic than Jennings. His career spanned five decades. As a result, it is impossible to boil it down to four tracks. However, the songs below are a good place to start.
“Stop the World (And Let Me Off)” from Folk-Country (1965)
When many people think of Waylon Jennings, they picture his signature shaggy hair and beard. However, that wasn’t always the case. Like many members of the Outlaw Country movement, he started as a clean-cut representative of the Nashville music industry machine. This was true for his major label debut Folk-Country.
Penned by Carl Belew and W.S. Stevenson, Jennings released this song as the second single from his debut record. It peaked at No. 16 on the Billboard Hot Country Songs chart, giving Ol’ Hoss his first top 20 hit. More importantly, it’s a solid introduction to his older catalog and a look at the beginning of a legendary career.
“Ain’t No God in Mexico” from Honky Tonk Heroes (1973)
Nearly a decade later, Waylon Jennings began to chafe under the yoke of label executives and heavy-handed producers. He pushed hard to gain creative control of his output and finally found it with Honk Tonk Heroes. While he had flirted with what would come to be known as the Outlaw Country sound, his 1973 release all but codified the sound.
Like nearly every other song on Honky Tonk Heroes, “Ain’t No God in Mexico” was written by Billy Joe Shaver. Jennings didn’t release the song about getting wild South of the Border as a single but it remains a standout track from the album.
For those who are unaware, Outlaw Country was never truly about crime, drug use, or anything else that many ascribe to the subgenre. Instead, it was all about creative expression. “For us, ‘outlaw’ meant standing up for your rights, your own way of doing things. It felt like a different music, and outlaw was as good a description as any,” he wrote in his 1996 autobiography.
“Don’t You Think This Outlaw Bit’s Done Got Out of Hand” from I’ve Always Been Crazy (1978)
While Outlaw Country as a movement was about creative expression, Waylon Jennings and other musicians associated with the movement weren’t exactly squeaky clean. This track from his 1978 album I’ve Always Been Crazy is an example of that. It also explores the scrutiny Jennings and other “outlaws” found themselves under.
Penned by Jennings, “Don’t You Think This Outlaw Bit’s Done Got Out of Hand” was a No. 5 hit. It is also the story of the time federal agents almost busted Jennings with a big bag of nose candy in a studio.
“Theme from The Dukes of Hazzard (Good OI’ Boys)” from Music Man (1980)
Countless people of all ages sang along with Waylon Jennings every week when The Dukes of Hazzard came on television. While the version he recorded for his 1980 album Music Man differs from the version used in the show in a handful of ways, it is close enough to be loved by fans of the show and those who have no idea who Bo and Luke Duke are.
This Jennings-penned classic went to No. 1 on the Billboard Hot Country Songs chart. Additionally, it landed at No. 21 on the all-genre Hot 100 chart, giving him his biggest crossover hit.
Featured Image by Larry Hulst/Michael Ochs Archives/Getty Images
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