The legacy of Texas outlaw Waylon Jennings takes on a new footing in the 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 ready to drive again.

Twenty years after his death, Jennings' name appears in song lyrics, his voice is present on two unreleased tracks about to hit the market, and his rebellious ways were one of the most talked-about elements of a recent Netflix documentary The Greatest Night in Pop.

Jennings, that film showed, walked away from Stevie Wonder, Michael Jackson, Bob Dylan and other bandmates during the epic 1985 recording of “We Are the World” when the all-star team went astray from attempts to sing part of the song in Swahili. Jennings' disappearing act had been vaguely mentioned before, but became one of the recurring gags in accounts of the film, which debuted in January.

It wasn't the last time Jennings left a live taping — he left host Tom Snyder in 1998 — but it was that kind of unique, hilarious approach to his life and career that helped make Jennings an icon. And that's why there's a bit of a revival of his legacy that could grow in the coming months.

“Waylon's genre is a mystery,” says songwriter Lee Thomas Miller (“In Color,” “It Ain't My Fault”). “I don't think people really know how dark it was and how intense it was. I mean, he was so politically incorrect and attacked [Country Music Association (CMA)]. But I feel like culturally, Waylon and Willie [Nelson] they're 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, which was released on April 5. The gritty performance — with its references to cocaine, rhinestones, anger and alcohol — comes close to capturing the spirit of Jennings during “his wild, woolly days,” says Jessi Colter, his wife and music partner for over 30 years. He cleaned up in 1984, although his fans are more obsessed with his rough days.

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

The appearance of “Waylon in '75” coincides with two recent charting singles that bring a Stetson to Jennings in their lyrics: George Birge's “Cowboy Songs” (No. 38, Country Airplay) and the John Morgan collaboration /Jason Aldean “Friends Like This” (no. 60). In both plots, Jennings' music provides the atmosphere for a male lead.

“I've been a big fan of Waylon Jennings for a long time,” says Birge. “Honky Tonk Heroes” is probably my favorite Waylon song. I've heard this song at least 10,000 times in my dad's truck. He had a five-disc CD player in his F-150, back when the CD player was under the rear seat of the cab. Of Greatest Hits it was one of the CDs on there, so I was definitely heavily influenced by Waylon. So it was probably no accident that when I subconsciously connected those lines, 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 the studios he used to make his recordings. The stomping guitars and bass became an edgy, signature sound, and he controversially asked the CMA to remove it from awards consideration, arguing that music should not be a competitive sport. He refused to attend when he was inducted into the Country Music Hall of Fame. It is this objective persona that earned him an “outlaw” label, along with Nelson, Colter, Tompall Glaser, Billy Joe Shaver, David Allan Coe and Johnny Paycheck, among others. This makes it all the more ironic that many country fans have come to see Jennings as a traditionalist.

“People now look back at all those guys with rose-colored glasses,” says “Friends Like That” co-writer Will Bundy. “But these guys that we think of as key pieces now have not been well received in some cases. They just did their thing.”

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

Miranda Lambert also adopted an aggressive stance that mirrored Jennings' approach. (He appropriately covered the Nelson/Jennings duet “Mammas, Don't Let Your Babies Grow Up To Be Cowboys” on the CBS special Willie Nelson's 90th Birthday Celebration in December.) And many of her fellow Texans — including Parker McCollum, who co-wrote Beckham's “Waylon in '75” — also owe a stylistic debt to Jennings.

“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 more attention now. And Waylon is the embodiment of that. It's the energy that's been the outlaw culture for quite some time.”

One of the ways Jennings changed the country sound was by adopting southern rock textures. He was known to use chords that deviated from the country norm, hardening the underlying progressions of his music and bordering on the blues. And a certain triad—which breaks standard key signatures while still sounding like it belongs—can still be heard in songs like Riley Green's “Damn Good Day To Leave” (No. 43).

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

Jennings appears among the backing singers on two Johnny Cash recordings from the early 1990s, “I Love You Tonite” and “Like a Soldier,” which appear on a new Cash album of unearthed material. Songwriter, due June 28 via Mercury Nashville. An earlier duet with Cash, the 1978 single “There Ain't No Good Chain Gang,” illustrates the fine vocal skills that made Jennings one of the most accomplished singers of his era. He navigates the verses' melodies in an understated, conversational tone, then launches into the raucous chorus with an emphatic, near-abandonment.

“There aren't many interpreters,” Colter argues. “He's the rock of the American folk music business, in my mind.”

And with country embracing a grittier tone, it makes sense that the individualistic spirit of Jennings and his fellow outlaws is quietly being rekindled during the genre's current revival.

“He was so instrumental to us in the way they wrote songs and the way they all sounded distinct,” says “Friends Like That” co-writer Brent Anderson. “We still listen to those records. They sound like no other. It's just them.”