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

Willie Nelson is opening up about the loss of one of his closest friends and collaborators, the late Kris Kristofferson.

In an interview with the Associated Press, Nelson reflected on Kristofferson’s death just weeks after the legendary songwriter passed away on Sept. 28 at age 88. Calling him a “great songwriter,” Nelson emphasized the lasting legacy Kristofferson leaves behind.

“He left a lot of fantastic songs for the rest of us to sing for as long as we’re here,” Nelson said. “Kris was a great friend of mine. 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 and Kristofferson were part of the iconic country supergroup The Highwaymen, formed in 1986 alongside Waylon Jennings and Johnny Cash. The group released three albums and toured extensively through the 1990s. With Jennings passing in 2002 and Cash in 2003, Nelson is now the last surviving member.

“When you go back to Waylon and Kris and John — all of us working together as the Highwaymen — and now I’m the only one left,” Nelson said. “That’s just not funny.”

Beyond music, Nelson and Kristofferson also shared a screen, appearing together in films such as Stagecoach (1986), Pair of Aces (1990) and its 1991 sequel, and The Long Kill (1999). Kristofferson’s final public performance took place at Nelson’s 90th birthday concert in April 2023, where he performed alongside Rosanne Cash.

Their bond ran deep for decades. “I think we are about as close as friends can be,” Nelson told Rolling Stone in 2009. “We understand all we need to understand about each other.”

Kristofferson’s wife, Lisa, echoed that sentiment, describing the rare closeness shared by The Highwaymen. “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 was real.”

Kristofferson died peacefully at his home in Maui, surrounded by family. In a statement, his family said they were grateful for the years they shared with him, adding, “When you see a rainbow, know he’s smiling down at us all.”