Waylon Jennings had spent years building a reputation as one of country music’s toughest personalities. The black hat, deep voice, and refusal to follow Nashville’s rules made Waylon Jennings the very picture of an outlaw.
But there was one man outside country music whom Waylon Jennings admired enormously: Muhammad Ali.
When Kris Kristofferson introduced the two legends during the 1970s, the meeting began a friendship that lasted far beyond their first conversation. Years later, that friendship would inspire a song whose remarkable story continued long after Waylon Jennings was gone.
The Meeting Kris Kristofferson Never Forgot
Kris Kristofferson already knew Muhammad Ali when Waylon Jennings expressed an interest in meeting the heavyweight boxing champion. Kris Kristofferson later recalled arranging their introduction at a restaurant in Los Angeles.
Waylon Jennings wasn’t someone who became excited about meeting celebrities. Yet Muhammad Ali was different.
Looking back on that introduction after Waylon Jennings died, Kris Kristofferson remembered two men with intimidating reputations behaving like “two little kids delighted with each other.”
The connection was immediate. Both men had challenged powerful establishments, spoken their minds, and built careers without apologizing for their independence.
And their friendship soon moved beyond a restaurant conversation.
The Night Muhammad Ali Became Champion Again
On September 15, 1978, Waylon Jennings attended Muhammad Ali’s historic rematch against Leon Spinks at the Louisiana Superdome in New Orleans.
Earlier that year, Leon Spinks had defeated Muhammad Ali and taken the heavyweight championship. Now Muhammad Ali was attempting to reclaim the title.
Waylon Jennings visited Muhammad Ali in the dressing room that evening. After fifteen rounds, Muhammad Ali won by unanimous decision, becoming the first boxer to win the world heavyweight championship three times.
Muhammad Ali gave Waylon Jennings a white boxing robe and training gloves associated with that historic fight.
Waylon Jennings kept those gifts for decades. In October 2014, the memorabilia appeared among the possessions offered at a major auction of the country singer’s estate in Phoenix.
But the friendship had a much more personal side.
The Unusual Story Jessi Colter Remembered
In a 2017 interview, Jessi Colter revealed that Muhammad Ali had become close enough to the Jennings family to attend the christening of Waylon Jennings and Jessi Colter’s son, Shooter Jennings.
Then came an extraordinary favor.
Waylon Jennings had purchased a tour bus that was not even fully furnished. Muhammad Ali asked to borrow it, drove the bus to Louisville, Kentucky, and eventually returned it.
Jessi Colter also remembered that Waylon Jennings kept a photograph of Muhammad Ali in every home the family occupied.
These were not gestures for publicity. They were details of an enduring personal friendship that many country music fans never knew existed.
The Song Waylon Jennings Wrote for Muhammad Ali
During the late 1990s, Waylon Jennings was working on material for a possible new album. Among those recordings was a tribute to Muhammad Ali titled “Here’s to the Champion (Muhammad Ali).”
Waylon Jennings recorded a demo, accompanying the tribute with the unmistakable voice that had defined decades of outlaw country music.
But the recording never received a commercial release during Waylon Jennings’ lifetime.
On February 13, 2002, Waylon Jennings died at home in Chandler, Arizona, at age 64.
That day, Kris Kristofferson remembered the longtime friend and fellow Highwaymen member as “the bad guy with the big heart.”
Yet the musical tribute to Muhammad Ali still had another chapter ahead.
The Night Muhammad Ali Heard His Friend’s Song Again
On March 19, 2010, Kris Kristofferson and Jessi Colter appeared at a private dinner in Phoenix associated with Muhammad Ali’s charitable fundraising efforts.
Before approximately 200 guests, Kris Kristofferson and Jessi Colter performed the song Waylon Jennings had written for the champion.
According to journalist Roger Friedman, who reported on the event the following day, the performance brought tears to Muhammad Ali’s eyes.
Eight years after Waylon Jennings’ death, the friendship was being remembered through a song that most listeners had never heard.
And the original recording was still waiting to reach the public.
Fifteen Years After Waylon Jennings’ Death
In 2017, Black Country Rock released a special collection built around “Here’s to the Champion (Muhammad Ali).”
The release included Waylon Jennings’ original demo, a version remixed by producer Dave Cobb, and interpretations involving Willie Nelson, Shooter Jennings, Jaime Wyatt, Kris Kristofferson, and Jessi Colter.
For the first time, listeners could hear Waylon Jennings’ own recorded tribute to the boxer who had become such an important friend.
It was a remarkable continuation of a story that began with Kris Kristofferson introducing two famous men in a Los Angeles restaurant.
When Kris Kristofferson remembered Waylon Jennings in February 2002, the first thing that mattered wasn’t an award, a hit record, or the outlaw image.
It was the heart behind that image.
And through a friendship with Muhammad Ali, a treasured collection of boxing memorabilia, and one long-unreleased song, that side of Waylon Jennings remained visible for generations of fans to discover.