Watch Kris Kristofferson’s Sob-Worthy Set at Willie Nelson’s Bday

Rosanne Cash brought Kris Kristofferson to the stage with a smile and walked him off the stage in tears. Their moving duet at Willie Nelson‘s 90th birthday party concert provides a lasting look at the iconic songwriter as he nears 90 himself.

Kristofferson — age 87 next month — 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 he love song.

During their April 29 performance, they sang it as “Lovin’ You Was Easier.”

The video above 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 during this moment — it’s as if both icons recognized the performance meant something.

• Kris Kristofferson is 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 always 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. There are no events or appearances listed on his official website.