The last time Kris Kristofferson ever performed in public, he was paying tribute to a friend. Showing up for others is something Kristofferson, who died Saturday at the age of 88, did his entire career, whether it meant insisting that John Prine receive a record deal, or showing public support to Sinead O’Connor when the world shunned her, or spending decades advocating on behalf of the United Farm Workers. On these two evenings, last April, Kristofferson was in Los Angeles helping an all-star cast of musicians pay tribute to his old pal, collaborator, and Highwaymen bandmate Willie Nelson on the occasion of Nelson’s 90th birthday.
Kristofferson’s billing stuck out the moment it was announced: He’d retired three years prior, in 2021, hadn’t appeared in public in two years, and had suffered from a series of serious health problems, including memory less, for more than a decade. On the first night, Rosanne Cash, the daughter of Kristofferson and Nelson’s other Highwaymen collaborator, begins by herself, singing “Loving Her Was Easier (Than Anything I’ll Ever Do Again),” a 1971 Kristofferson song that Nelson recorded in 1979.
Then, halfway through the first verse, Kristofferson, 86, struts onstage, and begins singing with Cash, her right arm wrapped around a man she’s known most of her life.
“Loving Her Was Easier” is a song about the way regret shapes memory and memory shapes regret. Kristofferson’s narrator lingers on the details that haunt him so many years later: the finger on his skin, her smile on his soul, the way she expanded his mind. It is, perhaps, the most affecting depiction of the one-that-got-away repentance in popular music.
But on this night in April 2023, Cash transforms the song. By the time she gets to the bridge, she changes the words (“you ain’t shamed to be a man/Or afraid to be a friend”) for the man she’s singing to, and “Loving Her Was Easier” becomes something much different: a tribute to kinship, a paean to the beautiful soul who composed it, an ode to friendship, a blessing for a life well lived and the precious time remaining, a song for Kris.
You can see the emotion welling up in both Kristofferson and Cash’s eyes as they continue to duet. After Kristofferson sings the second chorus, he whips his head back in a full grin, as if he’s too enraptured by the moment to take it all in. Then, the two old friends decide to sing the refrain once more as the song comes to an end, and this time it’s Cash who is overcome by the moment: Her voice chokes up somewhere between the words “easier” and “ever,” and she needs her mentor, her father figure, to help make it through the night one last time. Kristofferson finishes the last few words by himself, Cash embraces him in perhaps the most heartfelt hug ever caught on camera, and they walk off-stage holding each other.
This was not the final time Kristofferson sang one of his songs in public. The very next evening, he duetted with Norah Jones on “Help Me Make It Through the Night,” which was nearly as heart-wrenching. What once was a torch ballad was transformed into an anthem of perseverance and support — a community of songwriters not just honoring Nelson, but his longtime partner, Kristofferson.
