As the songwriter of legendary compositions like “Help Me Make It Through the Night,” “Sunday Mornin’ Comin’ Down,” and “Me and Bobby McGee,” Kris Kristofferson transformed lyrics into literature, elevating the craft to a legitimate American art form in a way few had done before. Part Romantic poet, part folk troubadour, part country-music storyteller, Kristofferson died Saturday at the age of 88.
Kristofferson’s rep, Ebie McFarland, confirmed the musician’s death, adding that the “artist, singer, songwriter, actor and activist … passed away peacefully in his home in Maui, Hawaii … surrounded by family.”
Songwriting was merely one aspect to the Renaissance man, who was also a Golden Globe-winning actor, Golden Gloves boxer, Rhodes scholar, author, U.S. Army veteran, pilot, and onetime record-label janitor. But it was his penetrating lyricism that caused a seismic shift in the perception of country music by the late Sixties. Well-educated (with a military discipline) though he was, he quickly fell in with the freshman class of “outlaw” singer-songwriters that would buck the star system and influence generations to come.
The eldest of three children, Kristoffer Kristofferson was born June 22, 1936, in Brownsville, Texas. His father, Lars, the son of a Swedish army veteran, was a pilot and a major general in the U.S. Air Force who went on to work for Pan American Airways. The family moved frequently, settling in San Mateo, California, when Kristofferson was in junior high. A model student who earned the nickname “Straight Arrow,” he graduated from high school in San Mateo in 1954, and went on to study creative writing at Pomona College, winning several prizes in a short-story contest sponsored by Atlantic Monthly magazine. Graduating Phi Beta Kappa in 1958, he received a Rhodes scholarship to England’s Oxford University.
Although intent on becoming a novelist, Kristofferson concentrated his studies on the poetry of William Blake, and penned and performed his first songs while studying at Oxford’s Merton College. In England, he cut his first singles (credited to “Kris Carson”) for Top Rank Records, although they went unreleased at the time. After earning a master’s degree in English literature from Oxford in 1960, Kristofferson, who planned to resume his studies there, flew home to California for Christmas break. Reuniting with an old girlfriend, Fran Beir, the couple married and had a daughter, Tracy, and a son, Kris. Instead of returning to Oxford, Kristofferson enlisted in the Army.
Kristofferson served as a helicopter pilot while in the Army and attained the rank of captain. During a three-year tour in West Germany (with his wife and daughter in tow), he organized a band, learning the Bob Dylan songs as recorded by Peter, Paul, and Mary (his band’s Dobro player gave him the folk trio’s LPs). On leave in the spring of 1965, Kristofferson took his first trip to Nashville. He had been tapped for a position teaching English literature at the U.S. Military Academy at West Point after leaving West Germany, but his two weeks in Nashville scuttled that plan. He became enamored of the songwriting circle, befriending songwriter and music publisher Marijohn Wilkin (“The Long Black Veil”), Bobby Bare (“Detroit City”), and producer Cowboy Jack Clement.
“I came down to Nashville,” Kristofferson told Rolling Stone in 2009. “I’d been playing in an Army band, so people introduced me around like I was somebody. Everybody still called me ‘Captain.’ And I wrote seven, maybe 11 songs that first week. I thought if I didn’t make it as a songwriter I would at least get material to be the Great American Novelist. The people and places I was seeing were more exciting than anything I’d ever come across.”
Kristofferson and his family settled in Nashville, where he continued to write songs. He took a job as janitor at Columbia Recording Studios (“Emptying ashtrays and sweeping floors,” he described it), in addition to working as a part-time helicopter pilot flying back and forth between offshore oil rigs in the Gulf of Mexico. A story about how he once landed his helicopter in Johnny Cash’s yard to give the country star his demo tape would become country-music apocrypha.
Kristofferson’s marriage to Fran began to crumble, and when their son developed health problems, the couple was faced with thousands of dollars in medical bills. The financial strain took its toll, and Kristofferson’s wife left with the children to live in California while he continued to pursue music.
That career path didn’t sit well with Kristofferson’s mother, who sent him a letter telling him he was throwing his life away by writing songs and idolizing Johnny Cash. Kristofferson and Cash later shared a laugh together when Clement showed Cash that infamous letter. “It’s always great to get a letter from home, isn’t it, Kris?” Cash joked.
In 1967, Kristofferson recorded his debut single as a performer, “Golden Idol,” which promptly flopped. His songwriting, however, took off, and his songs landed on the charts via artists like Roy Drusky (“Jody and the Kid”), Billy Walker (“From the Bottle to the Bottom”), Ray Stevens (“Sunday Mornin’ Comin’ Down”), Jerry Lee Lewis (“Once More With Feeling”), Faron Young (“Your Time’s Comin’”), and Roger Miller (“Me and Bobby McGee,” “Best of All Possible Worlds,” “Darby’s Castle”). By the end of the Sixties, as the folk scene was fading in New York, Kristofferson played the Bitter End in Greenwich Village, where luminaries including Bob Dylan saw him perform. Kristofferson was one of Nashville’s most in-demand songwriters, but he was still just getting started.
In 1969, Carl Perkins gave up a prime opening slot for Cash so that Kristofferson could make his Newport Folk Festival debut, with Cash introducing him. The Man in Black also let him hang around backstage at his weekly ABC show, which was being filmed at Nashville’s Ryman Auditorium. There, Kristofferson mingled with artists and hustled his songwriting demos. By the turn of the decade, a whirlwind of recognition as both songwriter and artist was underway. Signed by Fred Foster to Monument Records in 1970, Kristofferson released his eponymous LP, which featured new originals as well as some of his familiar hits for other artists. Although a Top 10 chart hit, the LP was otherwise unsuccessful.
After his sophomore release, 1971’s The Silver Tongued Devil and I, sold more briskly, Kristofferson’s debut album was rereleased as Me & Bobby McGee, capitalizing on the success of the title song, a posthumous Number One pop hit for Janis Joplin. Kristofferson and Joplin shared her house in Mill Valley, California, for a while, where jam sessions with fellow musicians, actors, and others were commonplace. (He played the Isle of Wight Festival in the summer of 1970, sharing the final day’s bill with Jimi Hendrix, who would die from an overdose just a few weeks later.)
In 1970, Ray Price released his countrypolitan recording of Kristofferson’s “For the Good Times,” which helped the composition win the Academy of Country Music’s Song of the Year. Cash’s version of “Sunday Mornin’ Comin’ Down” secured the Song of the Year award that same year from the Country Music Association. Kristofferson’s double win for Song of the Year in 1970 marked the only time a single individual has ever won the same award from the ACM and CMA in the same year for two different songs.
Dozens of artists as diverse as Jerry Lee Lewis, Joe Simon, and Patti Page continued to cut his songs, and Kristofferson would earn several Grammy nominations and win three trophies over his life, including Best Country Song for “Help Me Make It Through the Night” in 1971. A track from his second LP, the nostalgic “Lovin’ Her Was Easier (Than Anything I’ll Ever Do Again)” was a Top Five Adult Contemporary hit, marking his highest chart entry up to that point as a solo artist. The tune also reached the pop Top 30.
Simultaneous to his commercial breakthrough in music, Kristofferson made his film debut in Dennis Hopper’s 1971 film The Last Movie. A commercial and critical disaster, it was followed by the lead role in Cisco Pike, which also starred Gene Hackman, Karen Black, and musician Doug Sahm. In 1973, Kristofferson married his second wife, singer Rita Coolidge, and the couple had a daughter, Casey. His film work continued with an appearance in Cash’s The Gospel Road: A Story of Jesus, and he played an unemployed musician in Blume in Love. His role as Billy in Sam Peckinpah’s Pat Garrett and Billy the Kid, which also starred Bob Dylan, earned Kristofferson a BAFTA award nomination for Most Promising Newcomer. In 1974, he co-starred with Ellen Burstyn in the Oscar-winning Alice Doesn’t Live Here Anymore, directed by Martin Scorsese.
But two of Kristofferson’s most noteworthy early film roles were surrounded by publicity that somewhat obscured his exceptional performances. A controversial Playboy spread with co-star Sarah Miles accompanied the erotic 1976 drama The Sailor Who Fell From Grace With the Sea. That same year, he shared the screen with Barbra Streisand in the rock & roll reboot of A Star Is Born. The third-most profitable film of the year, it was nonetheless savaged by critics, with Streisand and Kristofferson’s volatile on-set clashes becoming the stuff of Hollywood legend.
By the end of the Seventies, Kristofferson had released nine solo albums with varying critical results. His first two LPs were buoyed by the ubiquity of their material and feature two of the most iconic lines in popular music: “Freedom’s just another word for nothin’ left to lose,” from “Me and Bobby McGee,” and “He’s a walkin’ contradiction, partly truth and partly fiction,” from “The Pilgrim, Chapter 33,” written about some of his comrades, including Cash and Hopper.
Border Lord, his third album, was largely a commercial disappointment. His fourth release in a two-and-a-half-year period, Jesus Was a Capricorn surfaced in November 1972, with a title cut that borrowed its melody from John Prine’s “Grandpa Was a Carpenter.” After several failed singles, Kristofferson earned his first — and only — country hit and his bestselling pop single as a solo artist: Inspired by both Larry Gatlin’s “Help Me” and an altar call while visiting a church with country singer Connie Smith at a desperately low point in his life, Kristofferson’s “Why Me” reached Number One on the country chart and spent 19 weeks on the pop survey as well, becoming one of the bestselling singles of the year.
Between duet albums with his wife Coolidge, Kristofferson released the 1974 LP Spooky Lady’s Sideshow, with several tracks chronicling the trappings of fame and addiction, mirroring his mounting battle with alcohol. He quit drinking after his Golden Globe-winning turn in A Star Is Born.
Kristofferson’s film career would continue over the next four decades, with Peckinpah directing him again in 1978’s Convoy. His next big-screen role was in 1980’s Heaven’s Gate, one of the most notorious box-office and critical flops of its time. Kristofferson would team with his longtime friend Willie Nelson for the 1984 film Songwriter, but a much more successful venture would emerge the following year as the two pals joined Cash and Waylon Jennings to record and tour as the Highwaymen. The supergroup would record Jimmy Webb’s “Highwayman,” which became Kristofferson’s second and final Number One country hit.
Kristofferson’s politically charged 1986 LP, Repossessed, his first solo project in five years, was highlighted by “They Killed Him,” a tribute to Gandhi, Jesus, and Martin Luther King Jr., which Dylan would later cover. Kristofferson continued to raise social awareness and address political causes throughout his career, beginning with a 1972 concert benefiting Cesar Chavez and United Farm Workers. In the Eighties, he traveled to Nicaragua and controversially criticized the U.S. involvement in the Contras’ attempts to overthrow the country’s ruling Sandinista National Liberation Front. His Central American activism inspired the 1990 concept album Third World Warrior.
“Not everybody agrees with what I’m saying,” Kristofferson told left-leaning magazine The Progressive in 1991. “But my shows are set up so, from beginning to end, the feeling is a belief in the human spirit. I don’t think you could come and argue with the principles. By the end of the show, the crowds always seem to be on their feet.”
Late-career solo albums included A Moment of Forever, in 1995, and The Austin Sessions, a 1999 collection of stripped-down versions of some of his best-known tunes with guest appearances from Alison Krauss, Steve Earle, and Mark Knopfler. These were followed by a trio of reflective LPs: This Old Road (2006), Closer to the Bone (2009), and Feeling Mortal (2013). In 2016, he released The Cedar Creek Sessions, a two-disc collection of his past songs rerecorded in Austin.
Of his later films, Kristofferson will perhaps be best remembered for his role as a sadistic sheriff in John Sayles’ 1996 masterful crime drama Lone Star, which was followed by appearances in the Blade trilogy and 1998’s A Soldier’s Daughter Never Cries, a fictionalized account of the life of From Here to Eternity author James Jones. Kristofferson acted in more than 50 films over the next two decades, including Bloodworth, Dolphin Tale, and Blaze, director Ethan Hawke’s 2018 biopic of songwriter Blaze Foley that would be Kristofferson’s final onscreen role. He quietly announced his retirement from touring, recording, and acting in January 2021.
In 1970, Kristofferson bought property in Hana, a secluded town on the Hawaiian island of Maui. In addition to his three older children, Kristofferson raised five children with his third wife, Lisa Meyers. As Kristofferson began suffering from memory loss later in his life (which he ultimately attributed to Lyme disease), Meyers became indispensable, traveling with her husband and helping him navigate interviews. When he was saluted with an all-star concert in 2017 or as the guest performer on the 2020 Outlaw Country Cruise (his final full performance), Meyers was by his side. She balked at calling herself Kristofferson’s manager though. “He’s unmanageable. You can’t manage him,” she told Rolling Stone. “Even if someone tells him to have a good day, he’ll say, ‘Don’t tell me what to do.’”
But that stubborn streak also helped Kristofferson achieve such artistic heights. He was uncompromising in his songwriting, his acting, and onstage, where he’d strum his guitar, play harmonica, and sing in his infamously craggy voice. “I don’t think I’m that good a singer,” he told Rolling Stone. “I can’t think of a song that I’ve written that I don’t like the way somebody else sings it better.”
Still, for all his trailblazing, he was also content to allow fate and his spirituality to guide him. “I really have no anxiety about controlling my own life,” Kristofferson told Rolling Stone in 2016. “Somehow I just slipped into it and it’s worked. It’s not up to me — or you. I feel very lucky that [life]’s lasted so long because I’ve done so many things that could have knocked me out of it. But somehow I just always have the feeling that He knows what He’s doing.”