Playin' it cool with Coolidge (GIF via GIPHY)

When I saw him and Sarah Miles naked, I learned a LOT.

Country-music legend Kris Kristofferson, the writer of timeless classics like “Me and Bobby McGee” and a Country Music Hall of Fame solo artist in his own right, died Saturday, September 28, 2024, at 88. A family statement reveals he died surrounded by loved ones on Maui, with no cause given.

Kristofferson had an incredible string of successes, his socially conscious work recorded by everyone from Bob Dylan to Patti Page. His breakthrough came after he landed a helicopter in Johnny Cash's Nashville yard, leading to Cash covering “Sunday Mornin' Comin' Down.'” It earned Kristofferson a Songwriter of the Year Award from the CMAs in 1970, and kick-started a solo career.

His most famous compostion was surely “Me and Bobby McGee,” which his ex, Janis Joplin, covered on what became her posthumous album Pearl (1971). Kristofferson's debut album was retitled Me and Bobby McGee, and sales promptly took off. He wound up with 18 solo studio albums and many collaborative albums, including three with his wife (from 1973-1980) Rita Coolidge and three as part of the supergroup the Highwaymen (himself, Cash, Willie Nelson and Waylon Jennings).

His biggest solo hit was the no. 1 country smash “Why Me” (1973).

As an actor, Kristofferson appeared in a wild mix of big hits — he was the Golden Globe-winning lead in Barbra Streisand's A Star Is Born (1976) — and wild flops. Among his biggest missteps were Pat Garrett and Billy the Kid (1973), the torridly sexualized The Sailor Who Fell from Grace with the Sea (1976) with Sarah Miles and the unfairly maligned Heaven's Gate (1980), which, as he predicted, received a re-evaluation over time. The less said about Convoy (1978), the better.

He was much more successful in Cisco Pike (1972), Semi-Tough (1977) and three Blade movies (1998-2004), and was Oscar-nominated for his musical contributions to Alan Rudolph's Willie Nelson vehicle Songwriter (1984).

TV hits include The Last Days of Frank and Jesse James (1986), Amerika (1987) and his narration of Dead Man's Gun (1997-1999).

Kristofferson's progressivism made him a bit of a pariah at times, which is perhaps why he was so valuable to Sinéad O'Connor in 1992. She appeared at a Bob Dylan tribute after disparaging the Pope on SNL and was roundly booed. Shaken, she was comforted when Kristofferson whispered in her ear, “Don't let the bastards get you down.”

He is survived by his wife Lisa, eight children and seven grandkids.