On This Day in 2021, a Legendary Outlaw Country Songwriter Quietly Retired After Decades of Unforgettable Music

On this day (January 27) in 2021, Kris Kristofferson announced his retirement from recording, performing, and acting. While most artists with a five-decade-long career would have made a high-profile announcement or plotted a farewell tour, Kristofferson chose a different strategy. The news that he was ready to bring his career to an end was easy to miss, buried in a press release about a management change.

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Kristofferson never found the chart success or name recognition that his fellow Highwaymen enjoyed. However, he wrote and recorded a long list of stellar songs. Without digging too deeply, his catalog includes classics like “Sunday Morning Comin’ Down,” “Me and Bobby McGee,” “Help Me Make It Through the Night,” and “Why Me.”

[RELATED: On This Day in 1973, Kris Kristofferson Landed His First and Only Solo No. 1 on the Country Albums Chart]

More than a songwriter and recording artist, Kritofferson was also an actor. He appeared in dozens of films, including Pat Garrett & Billy the Kid, Stagecoach, Payback, Planet of the Apes (2001), and the Blade trilogy.

Kris Kristofferson played his last show in January 2020 as part of the Outlaw Country Cruise. However, he didn’t know that when he closed his set with “Please Don’t Tell Me How the Story Ends” that it would be his final performance. Instead, his age, health issues, and the pandemic that stretched between 2020 and 2021 made retirement feel like a natural choice.

Kris Kristofferson Barely Announced the End of His Career

The announcement of Kris Kristofferson’s retirement came in a press release about a management change. The release stated that Morris Higham Management was taking over the management of the Kris Kristofferson estate, according to Variety.

“Honestly, the announcement was more about the new management changes,” Tamara Saviano, Kristofferson’s longtime manager, told the publication. “Including Kris’ retirement was an afterthought,” she added.

“It wasn’t any big stake in the ground, like, ‘I’m retiring! I’m not doing this anymore!’ It was an evolution, and it just felt very organic,” Saviano said. “It was like, ‘Yeah, let’s retire.’ To us on this side of the fence, it was an organic, normal, ‘things are changing’ thing… It didn’t feel like such big news to us. That’s why there was no announcement,” she explained.

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