In the 2016 Rolling Stone interview, Kristofferson said, “I really have no anxiety about controlling my own life. Somehow I just slipped into it and it’s worked. It’s not up to me – or you. I feel very lucky that [life]’s lasted so long because I’ve done so many things that could have knocked me out of it. But somehow I just always have the feeling that He knows what He’s doing. It’s been good so far, and it’ll probably continue to be.”
Despite the memory issues, he continued performing full sets up until the beginning of the pandemic in early 2020.
Among his final public appearances, Kristofferson participated in duets on both nights of the Willie Nelson 90th birthday celebration at the Hollywood Bowl in 2023, singing “Loving Her Was Easier (Than Anything I’ll Ever Do Again)” with Roseanne Cash on the first night and “Help Me Make It Through the Night” with Norah Jones on the second. Of his pairing with Cash, which was arguably the most moving moment of either night, Variety‘s reviewer wrote, “Kristofferson’s voice wasn’t built for sweet harmony singing even in the best of days. But how sweet it was, regardless, as Cash gave her spiritual uncle all the support he needed to make this sad memory song feel like a warm, communal hug.”
Bob Dylan held Kristofferson in such high regard that he quoted “Sunday Morning Coming Down” at length in an unexpectedly long speech accepting an award from the Recording Academy’s MusiCares Foundation in 2015.
Speaking about other songwriters, Dylan said, “Everything was all right until — until — Kristofferson came to town. Oh, they ain’t seen anybody like him. He came into [Nashville] like a wildcat, flew his helicopter into Johnny Cash’s backyard like a typical songwriter (laughter). And he went for the throat: ‘Sunday Morning Coming Down’:
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