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


Willie Nelson, 91, recently reflected on the passing of his longtime friend and former bandmate, Kris Kristofferson, who died on September 28 at the age of 88. In an interview with the Associated Press, Nelson praised Kristofferson as a “great songwriter” and expressed his sorrow over the loss. He remarked, “He left a lot of fantastic songs around for the rest of us to sing, for as long as we’re here.”

Nelson and Kristofferson shared a deep friendship and collaborated extensively, notably as part of the country supergroup The Highwaymen, alongside Waylon Jennings and Johnny Cash. Reflecting on their time together, Nelson said,

“He left a lot of fantastic songs around for the rest of us to sing, for as long as we’re here,” Nelson said. “Kris was a great friend of mine. And, you know, we just kind of 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.”

The Highwaymen, formed in 1986, released three albums over the next … and continued to tour into the … Jennings passed away in 2002, followed by Cash in 2003, leaving Nelson as the last surviving member of the group.

Reflecting on his time with The Highwaymen, Willie Nelson noted, “If you just take the music part of it and go back to, you know, Waylon and Kris and John and, you know, all of us working together, the Highwaymen. And then I am the only one left. And that’s just not funny.”

Beyond their musical collaborations, Nelson and Kristofferson co-starred in several films, including the 1990 TV movie Pair of Aces and its 1991 sequel, as well as Stagecoach in 1986 and The Long Kill in 1999.

Kristofferson’s final performance was at Nelson’s 90th birthday concert in April 2023, where he performed alongside Rosanne Cash.

In a 2009 interview with Rolling Stone, Nelson expressed the depth of their friendship, stating, “I think we are about as close as friends can be. I think we understand all we need to understand about each other.”

Lisa, Kris Kristofferson’s wife, highlighted the deep bond among The Highwaymen, emphasizing their genuine affection for one another. She remarked, “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. John and Kris’ last words to each other were ‘I love you.’ Same to Waylon. That’s rare for men, and it was real.”

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

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