Kris Kristofferson performed “Loving Her Was Easier (Than Anything I’ll Ever Do Again)” with Rosanne Cash at Willie Nelson’s 90th birthday celebration at the Hollywood Bowl in 2023, after retiring from performing and recording. That guest appearance came after what American Songwriter reported was his final full concert in 2020—but the available accounts do not establish that the 2023 duet was his last-ever stage appearance.
What was Kris Kristofferson’s final performance of “Loving Her Was Easier”?
The best-documented late-career performance of the song was a 2023 duet with Rosanne Cash at Willie Nelson’s 90th birthday celebration at the Hollywood Bowl in Los Angeles. The Associated Press reported the appearance after Kristofferson’s death. It was an occasional guest spot, not a full concert, and the reporting does not establish it as his final stage appearance.
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That distinction matters because a separate 2020 cruise-ship show was described by American Songwriter as Kristofferson’s final full concert. Its account says the set included “Loving Her Was Easier.” A full concert and a later guest appearance are different milestones, not competing claims about the same kind of event.
How the closing years fit together
| Year | What happened | What it establishes |
|---|---|---|
| 2020 | A cruise-ship show, reported retrospectively by American Songwriter as Kristofferson’s final full concert. | The reported full-concert milestone; the set reportedly included the song. |
| 2021 | Kristofferson retired from performing and recording, according to the Associated Press obituary. | Retirement did not rule out occasional guest appearances afterward. |
| 2023 | He joined Rosanne Cash to perform the song at Willie Nelson’s 90th birthday celebration at the Hollywood Bowl, as reported by the AP. | A documented post-retirement guest performance, not proof of a last-ever appearance. |
| 2024 | Kristofferson died at age 88, according to the AP. | The obituary documents both his retirement and the 2023 duet. |
Why the song is a fitting thread through those appearances
“Loving Her Was Easier (Than Anything I’ll Ever Do Again)” was one of Kristofferson’s own hit recordings. The Country Music Hall of Fame and Museum gives its peak at No. 29 on the pop chart. The song thus connects the reported 2020 full concert with the later duet: it was part of his own catalog and remained a song he performed as a guest.
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Nelson’s admiration for Kristofferson’s songwriting helps explain the personal weight of the birthday-event pairing. At a 2009 BMI award ceremony for Kristofferson, Nelson said, “There’s no better songwriter alive than Kris Kristofferson.” The AP also reported Nelson’s follow-up: “Everything he writes is a standard.”
Independent reader supportYour contribution helps us test, update, and keep practical guides available for everyone.A related concert film, not the 2023 duet
The Life & Songs of Kris Kristofferson offers another documented performance of “Loving Her Was Easier,” but it is a different event. Blackbird Presents says the 2016 tribute concert event was released in 2017 as a two-CD/two-hour DVD combo pack and lists the song among its performances. The release predates the Hollywood Bowl duet, so it does not document Kristofferson and Cash’s 2023 performance.
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