Rosanne Cash brought Kris Kristofferson to the stage with a smile and walked him off the stage in tears. It would prove to be one of the iconic songwriter’s final performances, and it came as a moving duet at Willie Nelson‘s 90th birthday party concert on April 29, 2023.

Kristofferson died on September 28, 2024. He was 88.

The songwriter-performer-actor joined Cash for “Lovin’ Her Was Easier,” a song he wrote and artists like Roger Miller made a hit. Waylon Jennings, Tompall Glaser and Cash (who cut a live version as “Lovin’ Him Was Easier” several years ago) would also record the love song.

During this performance, he and Cash sang it as “Lovin’ You Was Easier.”

Video of the moment shows a closeup look at the two singers and the pure joy written across Kristofferson’s face as he’s singing. Cash couldn’t be happier herself — it’s as if both icons recognized the performance meant something.

• Kris Kristofferson is best known for writing hit songs like “Me and Bobby McGee,” “Sunday Morning Coming Down” and “Help Me Make It Through the Night.”
• He officially retired in 2020.
• His last public appearance came in 2021, when he helped make Hank Williams Jr. a member of the Country Music Hall of Fame.

At 3:22 of the above below, one hears Cash and Kristofferson finish the song, and as they embrace, what sounds like her sob is caught on the microphone. A closeup shows that both singers appear to be fighting back tears as they walk off stage.

Fast-forward to 4:12 to see his salute and heartfelt acknowledgment of the audience’s approval.

Both stars would later re-join the show for an all star version of “Will the Circle Be Unbroken.” Kristofferson is also seen closing the second night of the two-day concert, helping the crowd sing “Happy Birthday” to Nelson.

Kris Kristofferson’s Lyme Disease Diagnosis

In the mid-2000s, Kristofferson was diagnosed with Alzheimer’s, but a decade later he’d reveal he was misdiagnosed and he was actually battling symptoms of Lyme disease. After he began receiving treatment, those close to him said they saw a dramatic improvement in his memory and cognition.

When his retirement was announced, his team left open the possibility that he might record again or even take a stage or two. Unfortunately, things didn’t play out that way. Kristofferson’s family revealed his death in a statement on Sunday, Sept. 29, noting:

“Thank you for loving him all these many years, and when you see a rainbow, know he’s smiling down at us all.”