On This Day: Waylon Jennings Plays Final Major Concert in 2000

by Madison Miller

Twenty years ago today, country legend Waylon Jennings was playing his final concert. Fans at the time, however, had no clue it would be their last time seeing the country outlaw performing in front of an audience.

Waylon Jennings’ Last Performance

In 2000, Jennings was forced to stop touring due to years of health problems. He had a cocaine addiction earlier in his life and used to smoke six packs of cigarettes a day.

Jennings ended up being diagnosed with diabetes, which caused pain and difficulties with mobility. He had his left foot amputated in 2001 and in 2002 died in his sleep from complications related to his diabetes.

Unfortunately for Jennings, he never got the chance for an epic last tour or goodbye tours like Glen Campbell or even Rascal Flats (announced in 2020). Instead, his last show didn’t feature any of the added emotion that normally comes with a goodbye. However, fans of Jennings know he wasn’t the type for a huge tribute to himself.

Now many consider his two-night concert at The Ryman Auditorium in Nashville, Tennessee his last performance.

Although he didn’t officially announce a goodbye tour, the way in which he selected songs and people to accompany him in 1999 was a walk down memory lane.

According to Saving Country Music, accompanying him was The Waymore Blues Band which he called his “hand-picked dream team.” They were a group of musicians that were close to his heart.

This included his drummer Richie Albright, steel-guitar player Robby Turner, session guitarist Reggie Young, and a complete horns section. There were 13 members in the epic band.

‘Never Say Die’

As for his final song choice, what better option was there than “Never Say Die.” Looking back, it seems like a defiant goodbye to the music world. In a 2007 DVD release of the show, Jennings is seen sitting down for most of the show. This isn’t to create a calm environment but was due to his pain that made it hard to stand.

“I guess y’all noticed I’m sittin’ on this chair. And that ain’t all old age. I kinda hurt my back and my legs. But I’m gettin’ around. Y’all don’t worry about me. I can still kick ass. You’ve just got to bring ’em up here … I don’t want you girls worrying about me either, ’cause once you’ve had a cripple, you never go back.”

Throughout his set he performed songs like “Good Hearted Woman,” “Amanda,” “Suspicious Minds,” “I’ve Never Been To Spain,” “The Weight,” and Toy Caldwell’s “Can’t You See.”

Country Music Hall of Fame

Looking back, The Highwayman singer’s Nashville performance symbolizes his last time on the stage and outlines his strength and comedic nature. Other fans, however, also remember one of the country legend’s other famous last moments.

In 2001, in the midst of many health problems, Jennings turned down the dinner event acknowledging new inductees into the Country Music Hall of Fame. This would have been one of the last times fans could hear and see Waylon Jennings.

Instead, Jennings sent his son Buddy Jennings to accept the reward. This could have been due to health problems and difficulty traveling, or the longstanding issues he had with the Country Music Association.

The honor in reality, didn’t mean much to the country singer.

 “I don’t want any more trouble. I’ve had trouble with them all through these years. I’m not a member of the CMA … I let one of my sons go there and accept it. I think it meant something to my kids, and that’s enough,” Jennings said, according to an article from MTV.

Despite his big shrug toward the award, he is no forever remembered as a country legend through music and awards.