💔 “That’s Just Not Funny”: Willie Nelson Mourns the Loss of Kris Kristofferson, His Final Fellow Highwayman
At 91 years old, country music legend Willie Nelson is mourning the passing of his dear friend, collaborator, and fellow Highwayman Kris Kristofferson, who died peacefully at his home in Maui on September 28, 2024, at the age of 88.
In a new interview with the Associated Press, Nelson opened up about how deeply Kristofferson’s death impacted him.
“Kris was a great friend of mine,” Nelson said. “We had a lot of fun together and made a lot of music together — videos, movies… I hated to lose him. That was a sad time.”
Nelson, still releasing music — including his latest album Last Leaf on the Tree — reflected on the incredible legacy Kristofferson leaves behind:
“He left a lot of fantastic songs around for the rest of us to sing, for as long as we’re here.”
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Willie Nelson and Kris Kristofferson at a benefit concert in Nashville in 2013.
🎶 The Last Highwayman Standing
In 1986, Nelson, Kristofferson, Johnny Cash, and Waylon Jennings joined forces to form the supergroup The Highwaymen — a country music dream team that released three albums and toured throughout the late ’80s and ’90s.
With Jennings passing in 2002 and Cash the following year, Nelson shared the bittersweet reality of outliving all of his legendary bandmates:
“If you just take the music part of it… all of us working together, the Highwaymen. And then I am the only one left. And that’s just not funny.”
The two men weren’t just musical partners — they were soul-deep friends. They starred together in several films, including Pair of Aces, The Long Kill, and Stagecoach.
Kristofferson’s final public performance was fittingly at Nelson’s 90th birthday concert in April 2023, where he shared the stage with Rosanne Cash.
“I think we are about as close as friends can be,” Nelson once told Rolling Stone. “We understand all we need to understand about each other.”
💫 A Decade of Love, Laughter, and Legends
Kristofferson’s wife Lisa described the bond among The Highwaymen as rare and profound:
“Audiences adored them, but they couldn’t know how great those men really were together behind the scenes… It was a decade of rolling laughter and love.”
She shared that Kris’s final words to both Waylon and Johnny were “I love you” — a testament to their deep friendship. “That’s rare for men, and it was real,” she said.
His family echoed that love in a final tribute:
“When you see a rainbow, know he’s smiling down at us all.”
Kevin Winter/WireImage
Willie Nelson and Kris Kristofferson rehearsing for the Grammys in 2014 in Los Angeles.
