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Willie Nelson and Kris Kristofferson were friends for years, even performing in the country supergroup the Highwaymen together. Nelson, along with many of his country music peers, have spoken very highly of Kristofferson’s songwriting. Nelson believes that Kristofferson helped usher in a renaissance in country music.

Willie Nelson praised Kris Kristofferson’s songwriting

Kristofferson admitted he didn’t see himself as a performer. While he sometimes enjoyed singing to a crowd, his primary love was writing songs. He knew he wanted to be a writer, even if he had to leave the music industry to do it.

“I came down to Nashville,” he told Rolling Stone in 2009. “I’d been playing in an Army band, so people introduced me around like I was somebody. Everybody still called me ‘Captain.’ And I wrote seven, maybe 11 songs that first week. I thought if I didn’t make it as a songwriter I would at least get material to be the Great American Novelist. The people and places I was seeing were more exciting than anything I’d ever come across.”

It took him time to find success, but he became a much-admired figure amongst other artists.

“All his integrity was just bleeding onto the vinyl,” Rosanne Cash said. “He raised the bar for modern songwriters to a stratospheric level.”

Nelson believed Kristofferson fundamentally changed country music.

“He kinda brought us out of the Dark Ages,” he said.

Kris Kristofferson performed at Willie Nelson’s 90th birthday party

Kristofferson and Nelson remained friends for years, with the former coming out of retirement to perform at Nelson’s 90th birthday concerts. He’d dealt with a series of health problems and had stayed away from the public eye for two years at that point.

During the first show, Kristofferson joined Cash onstage to sing his 1971 song “Loving Her Was Easier (Than Anything I’ll Ever Do Again).” The following night, he sang the song “Help Me Make It Through the Night” with Norah Jones.

The country legend died on Sept. 28

On Sept. 28, Kristofferson died in his home in Maui, Hawaii. His death inspired an outpouring of tributes from those who knew him, worked with him, and respected him.

Barbra Streisand, his co-star in A Star Is Born, said she thought he was “something special” from the moment she first saw him perform. Country artists, like Dolly Parton, Reba McEntire, and LeAnn Rimes Cibrian, posted statements about his death on social media. Martin Scorsese, who directed Kristofferson, in Alice Doesn’t Live Here Anymore, said working with him was one of the highlights of his life.

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“Right now, I’m on a small boat between Ustica and Palermo, listening to ‘Me and Bobby McGee,’ remembering Kris Kristofferson,” he wrote in a statement, per AP. “Just like half of the world, I was lucky enough to work with Kris. He was a poet. Truly. Inside and out. And a damn good actor, a remarkable screen presence. Spending time with Kris when we made Alice Doesn’t Live Here Anymore was one of the highlights of my life.”

Kristofferson was 88.