Waylon Jennings died peacefully at his home in Chandler, Arizona, on February 13, 2002, after a long fight with diabetes-related health problems. He was 64. Only two months earlier, doctors in Phoenix had amputated his left foot. When the Associated Press gathered words from his friends that week, Kris Kristofferson, who had recorded and toured with him in the Highwaymen alongside Johnny Cash and Willie Nelson, gave the line that has followed Waylon ever since:
“Waylon Jennings was an American archetype, the bad guy with a big heart.” — Kris Kristofferson, 2002
It is a short sentence, but it holds both halves of the man. Kris did not pretend the “bad guy” part was a costume. He just refused to let it be the whole story.
The bus he handed over without a second thought
If you want to see what Kris meant by the big heart, one of the best places to look is a story Waylon told himself, in his 1996 autobiography written with Lenny Kaye.
Not long after his son Shooter was born, Waylon had just bought a new tour bus, the one the band called Shooter I. It was so new it was not even furnished yet, and Waylon admitted he was not sure it had license tags. Muhammad Ali, who had come to Shooter’s christening, asked him for the keys. Waylon handed them over. Ali drove the bus to Louisville to see his mother, then brought it back.
Waylon’s verdict on the whole thing was simple: “He could have kept it for all I cared.” He went on to say Ali meant that much to him, and to the world.
That is the outlaw in the black hat, giving away a brand-new bus without blinking.
The friendship Kris started
The friendship began with Kris. He had known Ali since the 1970s, after Ali saw him in A Star Is Born, and he later called Ali probably the biggest hero of his lifetime.
In interviews in 2013, more than a decade after Waylon died, Kris remembered that Waylon, a man who was not impressed by anybody, wanted to meet Ali. Kris set it up at a restaurant in Los Angeles and admitted he was nervous about it, because Waylon was in bad shape in those years. He described his friend as looking like he had been up for a month. The two men became great friends anyway.
Waylon’s own memory puts the bond in a different room. In his autobiography, he recalled Kris bringing him back to Ali’s dressing room on September 15, 1978, the night Ali beat Leon Spinks in New Orleans to win the heavyweight title for the third time. Waylon remembered Ali as completely calm before the fight. When Waylon left, Ali just said his name and hugged him. Ali also gave him the white robe he had worn before the bout and his training gloves. The two accounts do not have to compete; they may simply be two different early meetings, each remembered by a different man.
A few months later the two had lunch in Los Angeles, and when Shooter was christened in 1979, Ali showed up, dropped onto the couch and joked that he had come to integrate the place.
The song Waylon left behind
Waylon wrote a song for his friend called “Here’s to the Champion.” It was not released while he was alive. It survived as a home demo on a cassette Shooter later found among his father’s things.
In March 2010, at a private dinner in Phoenix for about 200 supporters of Ali’s Parkinson’s foundation, Kris Kristofferson and Jessi Colter sang that song to Ali. A Showbiz411 columnist who was there reported that it brought Ali to tears. Colter told the columnist Waylon had written it but never got to perform it for anyone except the Champ himself.
Years later, Shooter’s label released Waylon’s original demo along with new versions, including one by Kris and Jessi together.
Kris kept telling the truth about him
Kris never sanded down his old friend. In 2006, when the two of them were inducted into Hollywood’s RockWalk, with Jessi standing in for Waylon, Kris called him an “angry, funny, burning creative spirit.” He added that he wished Waylon were there to enjoy the honor, or to hate it.
That was the Waylon Kris knew: the man who skipped his own Country Music Hall of Fame induction in 2001, and the man who, as Rodney Crowell put it after his death, had a tender heart under all the tough stuff.
Kris Kristofferson died on September 28, 2024. Among the many things he left behind was a single sentence that still says it best about Waylon Jennings.