Country icon Willie Nelson, the last survivor of the Highwaymen, lost his dear friend and fellow group member when Kris Kristofferson died on September 28, 2024. At age 88, he left behind a legacy that flowed through American music and film. Speaking with heart in an interview, Nelson spoke of this special friendship, their contribution to country music, and the hole that Kristofferson’s death tore in his life.
A Bond Forged in Music: The Highwaymen
In the mid-1980s, Nelson, Kristofferson, Johnny Cash, and Waylon Jennings combined their talents into what would be country music’s supergroup—the Highwaymen. It brought together each of their musical styles, which included a healthy dose of rebellion. Lining up in retrospect to such an era, Nelson said, “If you just take the music part of it and go back to, you know, Waylon and Kris and John, and, you know, all of us working together. And then I am the only one left. And that’s just not funny.” The group was instrumental in defining the “outlaw country,” challenging the slick norms of Nashville’s country music scene, and producing timeless hits like “Highwayman” and “Desperados Waiting for a Train.”
Kristofferson was a lauded singer-songwriter who imbued their collaborations with a singular style of poetic lyricism and personal introspection. Nelson remembered the camaraderie and laughter they shared, placing a premium on the special bond they forged as the “brothers” of outlaw country. Remembering Kristofferson, Nelson said he was a “great friend,” and as a songwriter, he leaves “fantastic songs around for the rest of us to sing, for as long as we’re here.”
Pain of Being the Last Standing Highwayman
As the years went by, with every death of a bandmate—Waylon Jennings in 2002, Johnny Cash in 2003, and now Kristofferson-Nelson stands as the last member of the Highwaymen—an emotional load that he admitted to being quite heavy. “I hated to lose him,” he said—those sad, sad words of watching the closest of one’s peers leave this world one by one. The losses remind him of his own mortality and contribution to country music.
Aside from mourning Kristofferson, Nelson has released an album in recent times called Last Leaf on the Tree, which looks back at life and loss and time passing. For Nelson, the work is one of paying homage to his friends Kristofferson and Jennings and a way to remember them. Echoes of friendship, loss, and resilience run deep throughout this album, which he has now dedicated to those he loved and with whom he performed.
Kristofferson’s Final Bow: A Bittersweet Farewell
This was an unexpectedly poignant turn for Kristofferson, his last public performance occurring at Nelson’s 90th birthday celebration this past April 2023. Kristofferson sang “Lovin’ Her Was Easier” along with Rosanne Cash, daughter of the late Johnny Cash, in front of an audience that could feel the emotional poignancy of such a moment. The performance, as Nelson and many others had the privilege of watching, was based on a belief in finality—a feeling that a form of reverence was being paid by one legend to another who had given a lot to music.
Kristofferson’s wife, Lisa, made it known to the public how her husband had spent his last years grateful and filled with love toward the people who listened to his music. “When you see a rainbow, know he’s smiling down at us all,” said his family in a statement. And that echoed in the thoughts of Nelson about Kristofferson regarding his effect on him and his music.
A Legacy Etched in Country Music
Kristofferson’s contribution to country music is immense, from classic songs like “Me and Bobby McGee” to “Sunday Morning Coming Down.” His collaboration within the group the Highwaymen represented a whole new concept of country music, now raw, pure, and possibly beautifully imperfect, with all the vagaries that come with life. As Nelson reflected, “He left a lot of fantastic songs around for the rest of us to sing.” For Nelson and Kristofferson, music was not just a career but a journey into the inner self, a story being told, and a rebellion against the mainstream.
Kristofferson’s legacy extends far beyond his music into acting, producing iconic roles in movies such as A Star is Born and Convoy. Nelson and Kristofferson acted together in the 1990 TV movie Pair of Aces and furthered that with ongoing projects throughout the years, each one laying another brick in the foundation of their friendship.
Reflections on Mortality and Resilience
As the world remembers Kristofferson, Nelson reflects on his own life and career and says, “I don’t feel bad. I don’t hurt anywhere. I don’t have any reason to worry about dyin’.” At 91, Nelson continued to tour, issue music, and carry the torch for outlaw country, though he admitted the death of his close friends has changed him. His recent work has been a testament to resilience and to the unbreakable spirit of those who shaped the genre—to leave an indelible mark on the world along with Kristofferson.
For fans and peers alike, the bond between Willie Nelson and Kris Kristofferson stands as one of the most prized moments in country music history. Their story—from fledgling artists to legends in their genre—celebrates the power of friendship, but perhaps more so, that two remarkable artists redefined what it means to be truly alive through their music and art.
