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One month after Kris Kristofferson’s death, Willie Nelson, spoke out about his dear friend.

Few friendships in Nashville have lasted as long as Willie Nelson and Kris Kristofferson’s. The two met early in their careers, although neither of them seemed to remember their first meeting, according to a 1984 interview with David Letterman.

Kristofferson told the talk show host at the time that had been trying to recall how long he had known Nelson, but couldn’t recall the first time they met. He surmised that the failed memory had to do with his adoration for Willie Nelson.

“I figure it’s because I sort of idolized him when I was in the Army and he was one of the hero songwriters. And then when I went to Nashville after I got out of the Army, I made 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 when I didn’t know him.”

In 1985, Willie and Kris, along with Waylon Jennings and Johnny Cash, formed The Highwaymen. The all-star lineup of outlaw country artists formed the supergroup and recorded three major label albums. They performed together as the Highwaymen for a decade before the declining health of Jennings and Cash forced them to disband.

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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.

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