Kris Kristofferson

Kris Kristofferson was a Grammy-winning songwriter-singer — in that order — responsible for some of country music and pop’s most well-crafted songs. A north star for fellow songwriters committed to bravely probing the human experience, Kristofferson excelled at writing about a loneliness that cannot be shook, about dreams that might never be achieved, and, to paraphrase one of his song titles, about the bottle to the bottom and everything in between.

The Texas native, who lived in Nashville, Los Angeles, and, in his final days, Hawaii, recorded the songs he wrote on a series of albums, beginning with his self-titled 1970 debut and ending with 2016’s The Cedar Creek Sessions. But it was other artists who often transformed his compositions like “Help Me Make It Through the Night” (Sammi Smith), “For the Good Times” (Ray Price), and “Me and Bobby McGee” (Janis Joplin) into radio hits. Still, despite not possessing the most mellifluous of voices, Kristofferson could drive home a song: His version of “Sunday Mornin’ Comin’ Down,” made famous by Johnny Cash, arguably packs more of a punch than the Man in Black’s, especially when Kristofferson croaks that forlorn line about “wishing Lord that I was stoned.”

Kristofferson — country music’s rogue poet — would become close friends with Cash and two other outlaw pioneers, Willie Nelson and Waylon Jennings. Together, they formed the Highwaymen, recording three albums and touring the globe, all the while singing one another’s songs. In fact, Kristofferson poked fun at the idea of song ownership in “Don’t Cuss the Fiddle,” a track off his 1975 LP Who’s to Bless and Who’s to Blame that was later covered by Nelson and Jennings: “We’re in this gig together/So let’s settle down and steal each other’s song,” they sang.

While Kristofferson found his initial success in music, he was far from defined as a musician. He served in the Army, flew helicopters, attended Merton College in the U.K. as a Rhodes scholar, threw hooks and jabs as a Golden Gloves boxer, and won a Golden Globe for his role opposite Barbra Streisand in 1976’s A Star Is Born. His filmography is vast, with roles including the truck-driving actioner Convoy, the Blade vampire-hunter series, the Willie Nelson vehicle Songwriter, and the Western Pat Garrett and Billy the Kid, opposite Bob Dylan. In John Sayles’ Lone Star, he was terrifying as a brutal sheriff. His final role was in Ethan Hawke’s 2018 biopic Blaze, about the tragic songwriter Blaze Foley.

Kristofferson quietly retired from touring, recording, and acting in 2021, but made a rare appearance onstage at a pair of 90th birthday concerts for Nelson in 2023. Kristofferson died Sept. 28, 2024, at age 88, leaving behind a legacy as a true American Renaissance man. — Joseph Hudak