During the evening, Waylon ran through some of his most memorable hits like “Good Hearted Woman” and “Amanda.” But at the time, Waylon was also very much playing music for himself with a hot shot band behind him, and he performed a large handful of cover songs, from “Suspicious Minds,” to “I’ve Never Been to Spain,” to “The Weight,” and one of his favorite songs to play live, Toy Caldwell’s “Can’t You See.”
Also joining Waylon on stage during the two night stint at the Ryman were his wife Jessi Colter who sang her signature song “I’m Not Lisa,” along some of the hottest names in popular traditional country at that time, including John Anderson who joined Waylon for “Waymore’s Blues,” Travis Tritt who traded lines on “I’ve Always Been Crazy,” and Montgomery Gentry who joined Waylon on “I’m a Ramblin’ Man.”
Waylon would go on to play some more shows after his January 6th, 2000 appearance at the Ryman Auditorium, but not many, and perhaps none more memorable. He underwent surgery later in the year to help improve the circulation in his legs, and then in 2001, had his left foot amputated due to diabetes.
Waylon was never one to make a big “to do” about himself. He skipped his own Country Music Hall of Fame induction in October of 2001, saying the distinction meant “absolutely nothing, if you want to know the truth about it,” sending his son Buddy to accept the award on his behalf. But at the time, Waylon’s health was in such serious decline, perhaps he was in an ornery mood, or didn’t want to be seen in public, or couldn’t make the trip from Arizona.
But the late-era Waylon Jennings his fans will always remember is the one captured on the Ryman stage on those two dates in early January of 2000, even if he was sitting down instead of standing at center stage. Still defiant, still making country his way, Waylon went out in style.
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