Kris Kristofferson, who died on Saturday at 88, was most revered for his songwriting, favoring an aphoristic style that surveyed the many detours a life could take. By the time he broke through, at nearly 34 years old, Kristofferson had swerved off prescribed courses a number of times. The son of an Air Force major general and a socially conscious mother, he’d been a Rhodes Scholar, an Army helicopter pilot and a family man before going all in on music in 1965, a decision that splintered his family and left him scuffling for money.

“I was working the Gulf of Mexico on oil rigs. I’d lost my family to my years of failing as a songwriter. All I had were bills, child support, and grief,” Kristofferson once said of writing “Me and Bobby McGee” in the late 1960s. “I was about to get fired for not letting 24 hours go between the throttle and the bottle. It looked like I’d trashed my act. But there was something liberating about it. By not having to live up to people’s expectations, I was somehow free.”

By the time success came in 1970 — as Ray Price’s cover of his song “For the Good Times” reached the Top 40 on the pop chart, and Johnny Cash’s version of “Sunday Morning Coming Down” became a No. 1 country hit — Kristofferson had experienced love, loss and hard times, all of which gave his career a hard-earned sagacity as it expanded over the next 50 years.

Here are some snapshots from his life and career.phlboss

ImageKris Kristofferson, an Oxford-educated Army helicopter pilot, turned down a teaching job at West Point to pursue songwriting in Nashville.Credit...Al Clayton/Getty ImagesImageKristofferson, in 1970 or 1971, in a Nashville hotel room listening to a reel-to-reel tape recorder after his appearance on “The Johnny Cash Show.”Credit...Al Clayton/Getty ImagesImageKristofferson in 1970, the year two songs he wrote — “For the Good Times” and “Sunday Morning Coming Down” — became hits for other artists.Credit...Al Clayton/Getty ImagesImageIn the liner notes of his 1971 album, “The Silver Tongued Devil and I,” Kristofferson described his music as “echoes of the going ups and coming downs, walking pneumonia and run-of-the-mill madness, colored with guilt, pride, and a vague sense of despair.”Credit...Don Paulsen/Michael Ochs Archives, via Getty ImagesImageKristofferson with Janis Joplin in the summer of 1970, shortly before her death in October of that year. Her version of “Me and Bobby McGee,” penned by Kristofferson, went to No. 1 on the Billboard Hot 100 chart in 1971.Credit...John Byrne Cooke Estate/Getty ImagesImageKristofferson starred opposite Barbra Streisand in Frank Pierson’s 1976 remake of “A Star Is Born.”Credit...Max B. Miller/Fotos International and Archive Photos, via Getty ImagesImageKristofferson and Streisand in a publicity photo from “A Star Is Born.” He won a Golden Globe Award for his performance.Credit...Screen Archives/Getty ImagesImageStreisand and Kristofferson at a preview of “A Star Is Born” in New York City in December 1976. She cast Kristofferson as the male lead in the film after seeing him onstage at the Troubadour in West Hollywood, Calif.Credit...Suzanne Vlamis/Associated PressImageKristofferson performing with Olivia Newton-John and Rod Stewart at a UNICEF benefit in New York City in 1979. His work in the 1980s and ’90s would venture into social justice and human rights.Credit...Ron Galella/Ron Galella Collection, via Getty ImagesImageKristofferson, center, with from left, Candice Bergen, Rita Coolidge, Willie Nelson and Burt Reynolds after a performance at the Bottom Line in New York City in 1979. Kristofferson and Coolidge, who were married for much of the 1970s, released three duet albums before divorcing in 1980.Credit...Associated Press/Associated PressImageKristofferson and Isabelle Huppert, with whom he appeared in the film “Heaven’s Gate” (1980), at the Cannes Film Festival in 1981.Credit...Associated PressImageKristofferson with Don King, commentating during a fight between Larry Holmes and Muhammad Ali in 1980. Kristofferson, a Golden Gloves boxer in college, was a lifelong fan of the sport.Credit...Randy Rasmussen/Associated PressImageKris Kristofferson and Jane Fonda at the premiere of the film “Rollover” in Los Angeles in 1981.Credit...Nick Ut/Associated PressImageWith Willie Nelson on the set of the film “Songwriter” in 1983.Credit...John Bryson/Getty ImagesImageFrom left, Nelson, Waylon Jennings, Johnny Cash and Kristofferson performing as the Highwaymen in 1985 at Nelson’s Fourth of July picnic in Austin, Texas.Credit...Beth Gwinn/Getty ImagesImageKristofferson, left, with Jackson Browne and Bonnie Raitt in San Francisco in 1989, performing in protest of the war in El Salvador. Credit...Tim Mosenfelder/Getty ImagesImageKristofferson comforted Sinead O’Connor after she was booed at Madison Square Garden in New York in 1992. “It seemed to me very wrong, booing that little girl,” he later said. “But she was always courageous.”Credit...Ron Frehm/Associated PressImageFrom left, Kristofferson, Victoria Williams, Suzanne Vega, Vin Scelsa and Lou Reed backstage at the Bottom Line in New York City in 1994.Credit...Ebet Roberts/Redferns, via Getty ImagesImageKristofferson joined Streisand onstage in London in 2019 for their duet “Lost Inside of You.” “He was as charming as ever, and the audience showered him with applause,” she wrote on social media after his death.Credit...Dave J Hogan/Getty ImagesImageKristofferson with Charlie McDermott in Vermont in 2005, during a break in the filming of “Disappearances.”Credit...Toby Talbot/Associated PressImageKristofferson performing with Nelson at a concert for Nelson’s 70th birthday in 2003. Credit...James Estrin/The New York TimesImageKristofferson performing at the Stagecoach Festival in Indio, Calif., in 2007. He retired from performing during the Covid-19 pandemic.Credit...Heidi Schumann for The New York Times

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