A Country Legend’s Last Waltz

As with many country artists who’ve risen to mythic proportions, Waylon Jennings went through several incarnations before he grew into the outlaw icon enshrined in the Country Music Hall of Fame. The first version of Jennings was the ambitious musician and obscure bass player who gave up his seat to a headliner on the doomed flight in 1959 that crashed and killed rock ‘n’ roll stars Buddy Holly, Ritchie Valens and J.P. “The Big Bopper” Richardson.

On the day the music died, Jennings took the tour bus and lived. His journey was just getting started.

A tall Texan with rugged good looks, he worked as a truck driver, a disc jockey and a jingle writer as he tried to make a name playing in the regional clubs. He cut demos, released songs and garnered a few minor hits. In the mid-‘60s, Jennings landed in Music City, signed to the A&M record label, then RCA Victor.

His second iteration was striking in its own right: a brooding Lone Star Jack Kerouac with  slicked-back pompadour and long sideburns, dressed in turtlenecks and suit jackets. 

A storm was brewing. Though Jennings had found success and charted a number of songs, including the Jimmy Bryant-penned “Only Daddy That’ll Walk the Line,” which presaged some hard rockin’ to come, he felt straight-jacketed by the rules of Music Row. When it came to making albums in the studio, record labels exerted total control. Producers were king, session players replaced road bands and artists were seldom allowed to pick their own material. Like Motown, Music Row was a hit factory, and artists had little say over the proceedings.

Waylon fought for his artistic freedom and ultimately won the right to make his music the way he saw fit (as did his compadre and collaborator Willie Nelson). It was a style — gritty, direct, bluesy, rocking and rhythmic — that connected with a broad audience in the ‘70s.

His progressive country-rock style has become a touchstone for subsequent generations of musicians, from Steve Earle and Travis Tritt to Uncle Tupelo and Jason Isbell.

With his long hair, scruffy beard, tinted shades, black hat and leather vest, he cultivated a hip cowboy-biker image that spoke to rock fans who normally wouldn’t be caught dead listening to a country artist. It was this final transformation of the artist, so beloved and notoriously hard-living, that fired the public’s imagination. His career yielded 16 No. 1 hit singles. His progressive country-rock style has become a touchstone for subsequent generations of musicians, from Steve Earle and Travis Tritt to Uncle Tupelo and Jason Isbell.

Forty years after Buddy Holly’s fateful flight, Jennings played his last major concert at Nashville’s Ryman Auditorium. “Never Say Die: The Complete Final Concert” captures the singer in fine, easygoing form. The legend remains seated on a center-stage stool for the duration of the show, trademark guitar in hand, sunglasses on and black hat in place. The artist is in his element, surrounded by his longstanding road band. He explains that he’s seated due to injury, not old age, and assures the audience he can still kick ass.

Jennings would die two years later in 2002 of complications due to diabetes, exacerbated by his early years of boozing, drugging and smoking. But at the Ryman, there’s no clue he’s running on borrowed time. He appears hale, hearty and happy to be making music.

 Thirty minutes in and he’s happiest of all. “I want you all to meet one of the sweetest, dearest people in the world,” he says “And she’s my wife: Jessi Colter.”

The eternally youthful Colter makes her entrance, smiling wide and dressed in a red sequined outfit. She takes a seat at the piano and plays a mini-set that includes her 1975 hit “I’m Not Lisa.” It’s a stirring performance. Halfway across the stage, Jennings leans back in his chair, transfixed by his wife of 30 years. He can barely break his gaze. 

The two got hitched in 1969. At the time, she had one divorce behind her. Jennings had three. The odds of a successful union weren’t good. But the marriage stuck, even when it threatened to derail in the mid-‘80s when Waylon hit peak cocaine abuse. Their son, the musician Shooter Jennings, was born in 1979. Waylon eventually got clean and sober for the sake of his child.

Watching Jennings and Colter’s startling and unabashed connection onstage, I recalled an interview I did with Shooter Jennings in 2005. He shared how his parents had always been a remarkable team, onstage and off.

“They just really loved each other, there was no two ways about it,” he said. “They both were just crazy about the other one. Throughout all the hard times, they made it through, and it showed in both of their characters. They’re survivors.”

The couple’s abiding adoration for one another is clear during their duet on the Colter-penned “Storms Never Last,” a song that packs an emotional wallop.

 “Oh, I have followed you down so many roads, baby,” Colter sings, gazing at her husband. 

Waylon looks back and responds in his trademark weathered baritone: “And every road we took, God knows, our search was for the truth.”

It’s a moving moment that encapsulates a career, a marriage and Jennings’s bittersweet last waltz.


Waylon Jennings “Never Say Die” Setlist

  1. Never Say Die

  2. Good Hearted Woman—>Mamas Don’t Let Your Babies… (Ed Bruce cover)

  3. Trouble Man

  4. Amanda—>A Couple More Years

  5. Waymore’s Blues

  6. It’s the World’s Gone Crazy (Cotillion)

  7. Love’s the Only Chain (Jessi Colter cover)

  8. I’m Not Lisa (Jessi Colter cover)

  9. Storms Never Last (Jessi Colter cover)

  10. Suspicious Minds (Mark James cover)

  11. Closing in on the Fire

  12. I’m a Ramblin’ Man (Ray Pennington cover)

  13. Help Me Make It Through the Night (Kris Kristofferson cover)

  14. Havin’ a Good Time

  15. Shakin’ the Blues

  16. Nothing Catches Jesus by Surprise

  17. Never Been to Spain (Hoyt Axton cover)

  18. Drift Away (Mentor Williams cover)

  19. I’ve Always Been Crazy

  20. Goin’ Down Rockin’

  21. The Weight (The Band cover)

  22. Can’t You See (Marshall Tucker Band cover)

Chrissie Dickinson is an award-winning music and arts journalist whose work has appeared in numerous publications, including the Chicago Tribune, Washington Post, Los Angeles Times, Christian Science Monitor, Performing Songwriter, Country Music Magazine and Off Our Backs. Her essays have appeared in a number of books, including “Ring of Fire: The Johnny Cash Reader” (DaCapo Press). Previously, she was the pop music critic at the St. Louis Post-Dispatch and was on staff at the Country Music Hall of Fame and Museum in Nashville, where she was editor of “The Journal of Country Music.”

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