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

Kristofferson, Nelson's one-time Highwaymen bandmate, died on Sept. 28 at age 88

Willie Nelson is reflecting 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 one month after Kristofferson died on Sept. 28 at age 88.

“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.”

Nelson and Kristofferson formed the country supergroup The Highwaymen in 1986 alongside Waylon Jennings and Johnny Cash. The group released three albums over the next decade, and continued to tour into the late 1990s. Jennings died in 2002, and Cash the year after, leaving Nelson the last group member standing.

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“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,” the told the AP.

The country legend — who released his new album Last Leaf on the Tree on Nov. 1 — also starred with Kristofferson in the 1990 TV movie Pair of Aces, as well as its 1991 sequel, plus others including Stagecoach in 1986 and The Long Kill in 1999.

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

“I think we are about as close as friends can be,” Nelson told Rolling Stone in 2009. “I think we understand all we need to understand about each other.”

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Kristofferson’s wife Lisa also praised the camaraderie of The Highwaymen to the outlet, noting their true adoration for one another.

“Audiences adored them, but they couldn’t know how great those men really were together behind the scenes,” she said. “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.”

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

“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," his family said in a statement shared with PEOPLE.