Willie Nelson Says Kris Kristofferson's Death Was a 'Sad Time': 'Hated to Lose Him'

Willie Nelson reflects on the death of his longtime friend and former bandmate Kris Kristofferson.

Nelson, 91, praised the late star as a “great songwriter” in an interview with The Associated Press, just over a month after Kristofferson’s death on Sept. 28 at age 88.

“He left a lot of great songs for the rest of us to sing as long as we’re here,” Nelson said. “Kris was my great friend. And, you know, we just had a lot of fun together and we made a lot of music together – videos, movies. I hated to lose him. It was a sad time.”

Nelson and Kristofferson formed the country supergroup The Highwaymen in 1986 along with Waylon Jennings and Johnny Cash. The group released three albums over the next decade and continued to tour in the late 1990s. Jennings died in 2002 and Cash a year later, leaving Nelson as the last member of the group.

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Willie Nelson and Kris Kristofferson at a benefit concert in Nashville in 2013.

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“If you just take the music part and go back to, you know, Waylon and Kris and John and, you know, all of us working together, the Highwaymen. And then only I remain. And that’s just not funny,” he told the AP.

Country legend — who released his new album The last leaf on the tree November 1 — also starred with Kristofferson in the 1990 TV movie A pair of acesas well as its 1991 sequel, including others Stagecoach in 1986 and Long murder in 1999.

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Kristofferson’s last performance before his death was at Nelson’s 90th birthday concert in April 2023, during which he performed with Rosanne Cash.

“I think we’re as close as friends can be,” Nelson said Rolling Stone 2009. “I think we understand everything we need to understand about each other.”

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Country singer-songwriter Willie Nelson, Waylon Jennings, Johnny Cash and Kris Kristofferson perform as the Highwaymen at Willie Nelson's 4th of July Picnic on July 4, 1985 in Austin, Texas.

Willie Nelson, Waylon Jennings, Johnny Cash and Kris Kristofferson perform in 1985.

Beth Gwinn/Getty

Kristofferson’s wife Lisa also praised The Highwaymen’s friendship until the exit, noting their genuine adoration for each other.

“The audience loved them, but they couldn’t know how great these people really were together behind the scenes,” she said. “It was a decade of laughter and love. John and Kris’ last words were ‘I love you’. Same for Waylon. That’s rare for men, and it was real.”

The star was surrounded by family when he died “peacefully” at his Maui home in September.

“It is with heavy hearts that we share the news that our husband/father/grandfather, Kris Kristofferson, passed away peacefully on Saturday, September 28th at home. We are all so blessed to spend time with him. Thank you for loving him all these years, and when you see a rainbow, know that he’s smiling down on us all,” his family said in a statement shared with PEOPLE.

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