Few friendships in Nashville have stood the test of time quite like that of Willie Nelson and Kris Kristofferson. The two first crossed paths early in their careers, though in a 1984 interview with David Letterman, they admitted neither could recall exactly when that initial meeting happened.
Kristofferson shared with the talk show host that he had tried to remember exactly how long he had known Nelson but couldn’t pinpoint their first meeting. He guessed that his admiration for Willie had something to do with the hazy memory.
“I figure it’s because I sort of idolized him when I was in the Army, and he was one of the hero songwriters,” Kristofferson explained. “Then when I went to Nashville after I got out of the Army, I became friends with a lot of guys who had been fired by Willie… and he kind of worked his way into my consciousness, and I don’t remember a time when I didn’t know him.”
In 1985, Willie Nelson and Kris Kristofferson teamed up with Waylon Jennings and Johnny Cash to form The Highwaymen. This legendary supergroup of outlaw country artists recorded three major label albums and performed together for a decade. Their time as The Highwaymen came to an end as Jennings’ and Cash’s health began to decline, leading to the group’s disbandment.
The men remained dear friends until Waylon and Johnny’s deaths in 2002 and 2003, respectively.
Willie Nelson and Kris Kristofferson went on to participate in other projects together, including movies such as The Long Kill and Outlaw Justice, and special guest vocal performances and collaborations.
Willie Nelson is now the last surviving member of the Highwaymen.
Willie remained quiet about the passing of his dear friend for a month. But in an interview with AP published roughly a month after Kristofferson’s death, the “On The Road Again” singer reflected on Kris’s death and called it “a sad time.”
“He was a great songwriter. He left a lot of fantastic songs around for the rest of us to sing for as long as we’re here,” he told the outlet. “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.”
He went on to reflect about being the only surviving member of the Highwaymen, saying: “That’s just not funny.”
But he’s not worried about dying. Willie told the outlet that he feels good and is in good shape.
“Well, I’m 91 plus, so, you know, I’m not worried about it. I don’t feel bad. I don’t hurt anywhere. I don’t have any reason to worry about dying. But I don’t know anybody who’s lived forever,” he says. “I take pretty good care of myself. And I feel like I’m in pretty good shape physically.”
Kris Kristofferson’s last public performance was at Willie Nelson’s birthday party in 2023.
Kris Kristofferson retired from performing in 2020, but made a special appearance at Willie Nelson’s 90th birthday celebration in 2023.
Kristofferson appeared alongside Johnny Cash’s daughter, Roseanne, to sing “Lovin’ Her Was Easier,” a song Kris wrote. But, at Willie’s party, Kris and Roseanne sang the lyrics as, “Lovin’ You Was Easier.”
The performance was an emotional one for Kris and Roseanne who embraced and fought back tears as the song concluded.
Watch the emotional moment unfold in the video below.