The Legacy of Texas Outlaw Waylon Jennings Gains a New Foothold in Current Country

What Goes Around Comes Around. The title of a 1979 Waylon Jennings album is almost prophetic in 2024, as one of country’s original outlaws is poised to ride again.

Twenty years after his death, Jennings’ name is appearing in song lyrics, his voice is present on two previously unreleased tracks about to reach the marketplace, and his rebel ways were one of the most talked-about elements in the recent Netflix documentary The Greatest Night in Pop.

Jennings, as that film demonstrated, walked out on Stevie Wonder, Michael Jackson, Bob Dylan and other fellow stars during the epic 1985 recording session for “We Are the World,” when the all-star assemblage got sidetracked by efforts to sing part of the song in Swahili. Jennings’ disappearing act had been vaguely reported before, but it became one of the anecdotes that appeared repeatedly in accounts of the film, which debuted in January.

It was not the last time Jennings would leave a live taping — he walked out on talk show host Tom Snyder in 1998 — but it was that kind of singular, headstrong approach to his life and career that helped make Jennings an icon. And it’s why there’s a small resurgence of his legacy that could grow in the months to come.

“Waylon’s kind of a mystery,” says songwriter Lee Thomas Miller (“In Color,” “It Ain’t My Fault”). “I don’t think people really know how dark he was and just how intense he was. I mean, he was so politically incorrect, and he lashed out at the [Country Music Association (CMA)]. But I feel like culturally, Waylon and Willie [Nelson] are almost mythical, Marvel characters or something.”

Miller is one of four songwriters behind “Waylon in ’75,” a track on Chayce Beckham’s debut album, Bad for Me, released April 5. The rough-cut performance -— with its references to cocaine, rhinestones, anger and alcohol — comes close to capturing Jennings’ spirit during “his wild, wooly days,” says Jessi Colter, his wife and musical partner for more than 30 years. He cleaned up in 1984, though followers are more obsessed with his hard-living days. 

“It’s fun in your 20s and early 30s,” Colter allows. “The taste of destruction is very appealing.”

The appearance of “Waylon in ’75” overlaps with two newly charted singles that tip a Stetson to Jennings in their lyrics: George Birge’s “Cowboy Songs” (No. 38, Country Airplay) and the John Morgan/Jason Aldean collaboration “Friends Like That” (No. 60). In both plots, Jennings’ music provides the atmosphere for a male protagonist.

“I’ve been a major Waylon Jennings fan for a very long time,” says Birge. “ ’Honky Tonk Heroes’ is probably my favorite Waylon song. I’ve listened to that song no less than 10,000 times in my dad’s truck. He had a five-disc CD player in his F-150, back in the days where the CD player was under the back seat of the cab. His Greatest Hits was one of the CDs in there, so I definitely was very, very heavily influenced by Waylon. So it’s probably not an accident when I was subconsciously throwing those lines together, that name came out.”

In the 1970s, some Nashville executives considered Jennings a troublemaker. He fought — and won — a battle with RCA over the arrangements and studios he used to make his recordings. Phased guitars and stomping basslines became an edgy, signature sound, and he controversially asked the CMA to remove him from awards consideration, maintaining that music should not be a competitive sport. He declined to attend when he was inducted into the Country Music Hall of Fame. It’s that against-the-grain persona that earned him an “outlaw” label, along with Nelson, Colter, Tompall Glaser, Billy Joe Shaver, David Allan Coe and Johnny Paycheck, among others. That makes it all the more ironic that many country fans have come to view Jennings as a traditionalist.

“People now look back at all those guys with rose-colored glasses,” “Friends Like That” co-writer Will Bundy says. “But those guys that we look at as staple pieces now weren’t really well received in some cases. They just sort of did their own thing.” 

They set a tone for their era, and their lone-ranger musical spirit became the standard that the current crop of hit-makers is judged against. “I think guys like Aldean, and even Morgan [Wallen] and HARDY, they’re guys who do that,” suggests Bundy. “They might not really play by the rules, but, you know, they don’t care. Which is refreshing.”

Miranda Lambert likewise adopted a feisty attitude that mirrors Jennings’ approach. (She appropriately covered the Nelson/Jennings duet “Mammas, Don’t Let Your Babies Grow Up To Be Cowboys” on the CBS special Willie Nelson’s 90thBirthday Celebration in December.) And many of her fellow Texans — including Parker McCollum, who co-wrote Beckham’s “Waylon in ’75” — also owe Jennings a stylistic debt.

“You see guys like Cody Johnson really killing it on the radio, and guys like Parker McCollum,” Beckham says. “The red-dirt stuff — I think a lot of it is getting a little bit more attention now. And Waylon is the embodiment of that. He’s the energy that has been the outlaw culture for quite some time.”

One of the ways Jennings changed the sound of country was his adoption of Southern rock textures. He was known to employ chords that departed from country norms, that toughened up his music’s underlying progressions and bordered on the blues. And one particular triad — which breaks standard key signatures while sounding like it still belongs — can still be heard in songs like Riley Green’s “Damn Good Day To Leave” (No. 43).

“The major two is an old-school country move, kind of a Waylon Jennings move,” suggests “Damn Good” co-writer Jonathan Singleton.

Jennings appears among the background singers on two Johnny Cash recordings from the early 1990s, “I Love You Tonite” and “Like a Soldier,” featured on a new Cash album of unearthed material, Songwriter, due June 28 through Mercury Nashville. A previous duet with Cash, the 1978 single “There Ain’t No Good Chain Gang,” illustrates the subtle vocal skills that made Jennings one of his era’s most adept singers. He navigates the verse melodies with an underplayed conversational tone, then launches into the raucous chorus with an emphatic, near-abandon.

“There’s not a whole lot of interpreters,” Colter maintains. “He is the rock of the American popular music business, in my mind.”

And with country embracing a grittier tone, it only makes sense that the individualistic spirit of Jennings and his outlaw peers is being quietly rekindled during the genre’s current resurgence.

“They were so instrumental to us in the way that they wrote songs and the way that they just all sounded distinctly themselves,” says “Friends Like That” co-writer Brent Anderson. “We still listen to those records. They sound like nobody else. It’s just them.” 

Related Images: