One month after the passing of Kris Kristofferson, Willie Nelson finally spoke about the loss of his close friend. Their friendship was one of Nashville’s longest-lasting, beginning early in their careers. In fact, neither Willie nor Kris could quite recall their first meeting. In a 1984 interview with David Letterman, Kris shared that he’d tried to remember how long he’d known Willie but couldn’t pinpoint their first encounter.
He guessed that his admiration for Willie had something to do with his hazy memory, saying, “I figure it’s because I sort of idolized him when I was in the Army. He was already one of my songwriting heroes. 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.”
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In 1985, Willie and Kris joined forces with Waylon Jennings and Johnny Cash to form The Highwaymen, a supergroup that brought together some of country’s most iconic outlaw voices. They recorded three albums together and toured for a decade before Waylon and Johnny’s declining health ultimately led to the end of their live performances as a group. Despite the end of The Highwaymen’s touring days, the bond between these men remained strong until Waylon and Johnny’s deaths in 2002 and 2003.
Even after that chapter ended, Willie and Kris continued to collaborate on various projects. They appeared together in movies like The Long Kill and Outlaw Justice and recorded special guest performances for each other’s albums. Through it all, their friendship remained a central part of their lives, with Willie now being the last surviving member of The Highwaymen.
After Kris’s passing, Willie stayed quiet for about a month, only later sharing his reflections in an interview with AP. He admitted that the loss of Kris marked a truly sad time for him. Kris had been a close friend, a brilliant songwriter, and a creative partner who left behind a legacy of songs that would be cherished by fans and fellow musicians alike. In the interview, Willie reflected on the times they’d spent together, saying, “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.”
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Thinking about being the last member of The Highwaymen left a bit of a sting for Willie, who simply remarked, “That’s just not funny.” Still, Willie isn’t worried about his own mortality. At 91, he’s found peace with the reality of aging, adding that he feels good and is in no hurry to leave this world. “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 shared lightheartedly. “I take pretty good care of myself. And I feel like I’m in pretty good shape physically.”
One of Kris Kristofferson’s last public appearances was at Willie’s 90th birthday celebration in 2023. Although Kris had retired from performing in 2020, he made an exception for his friend’s milestone birthday. Joined by Johnny Cash’s daughter, Roseanne, Kris sang “Lovin’ Her Was Easier,” a song he’d originally written himself. At Willie’s party, however, Kris and Roseanne changed the lyrics slightly, singing “Lovin’ You Was Easier” as a tribute to their friendship.
It was a moving performance, as both Kris and Roseanne embraced at the end, holding back tears as they finished the song. This touching moment between old friends was one of Kris’s last times on stage, marking the end of a remarkable career and a long-standing friendship with Willie.
