Kris Kristofferson, country music singer-songwriter, dies at 88

By John Johnson Jr.

Sept. 29, 2024 Updated 3:58 PM PT

He disliked being called a poet and thought, more or less accurately, that he sang like a barking bullfrog, but Kris Kristofferson did more to change country music than a legion of golden-throated balladeers.

“You can look at Nashville, pre-Kris and post-Kris,” Bob Dylan once said. “Because he changed everything.”

Meticulously crafting songs that were mournful and fatalistic without being mawkish, Kristofferson invited listeners to share the regrets of a man who let his lover slip away in “Me and Bobby McGee.” The ache of a lonely nighthawk seeking a friend to “Help Me Make It Through the Night.” Rolling Stone magazine said his influence ranged well beyond the confines of country music, calling him simply “one of the greatest songwriters of all time.”

Barbra Streisand, left, and Kris Kristofferson appear at a preview of the film "A Star Is Born."

The former Rhodes scholar and Army Ranger fashioned a second career as a leading man in Hollywood, co-starring with Barbra Streisand in a remake of “A Star Is Born,” for which he won a Golden Globe.

“He could dig for the simple truth of a character,” said John Sayles, who directed him as a ruthless lawman in “Lone Star.” Just as important, “Kris Kristofferson knows how to wear the boots.”

Beset with health problems, Kristofferson died at his home in Maui, Hawaii, on Saturday, family spokeswoman Ebie McFarland said in an email shared with The Times. He was 88. McFarland said Kristofferson died peacefully, surrounded by his family.

“We’re all so blessed for our time with him,” the Kristofferson family said later in a statement. “Thank you for loving him all these many years, and when you see a rainbow, know he’s smiling down at us all.”

Kristofferson was born June 22, 1936, in the Texas border town of Brownsville, the eldest son of a family with a distinguished military past. His father was an Army major general, and it seemed for a while that his son would choose the same dutiful path. In his youth, the family moved frequently before finally settling in San Mateo. Kristofferson became a Golden Gloves boxer and, despite his slender 5-foot-11 frame, a standout collegiate football player at Pomona College.

Kris Kristofferson in 1972 holding a guitar.

But he yearned for the artist’s life and was emboldened at 18, when he won a prestigious short story contest sponsored by the Atlantic Monthly. While studying literature at Oxford University in the early 1960s under a Rhodes scholarship, he wrote two novels and was crushed when publishers rejected them.

“I think I sort of despaired of ever making my living as an artist, until I went to Nashville,” he said.

In a rush to equip himself with all the trappings of the conventional life he thought he should live, he married his childhood sweetheart, had a daughter, enlisted in the Army and was deployed to Germany as a helicopter pilot. After he was discharged, the Pentagon offered him a teaching position at West Point. It was a career-making honor, but Kristofferson decided to first stop in Nashville to see if he could sell songs he’d been working on with Army buddies in a band he named the Losers.

It took just two weeks to change his path once more, this time for good. “I fell in love with the whole life, of songwriters hanging out writing songs to each other,” he said. He turned down the West Point offer and moved to Nashville.

“It was pretty scary,” he recalled decades later.

It also was deeply unpopular with his family. His mother disowned him, writing that whatever he achieved would never measure up to the “tremendous disappointment you’ve always been.” It was an awful sentiment, but Kristofferson felt something he’d never experienced as the dutiful, high-achieving son: freedom. The search for freedom, and the suffering that came along with his refusal to meet the expectations of others, would lie at the heart of his art.

“He’s unmanageable,” his third wife, Lisa Meyers, would later say. He backed out of a lucrative contract for his autobiography rather than accept a deadline imposed by the publisher. “Even if someone tells him to have a good day, he’ll say, ‘Don’t tell me what to do,’” Meyers said.

The years of struggle on Music Row did little to validate Kristofferson’s choice to throw over his military career. To support his family, he took side jobs, from bartender to helicopter pilot, transporting workers to oil rigs in the Gulf of Mexico. Finally fed up with the meanness of their life, his first wife, Frances Beer, left him and took their young daughter. He captured the misery of that time in one of his most heartfelt songs, “Sunday Morning Coming Down.”

“Well, I woke up Sunday morning with no way to hold my head that didn’t hurt / And the beer I had for breakfast wasn’t bad, so I had one more for dessert.”

“Sunday was the worst day of the week if you didn’t have a family,” he said. “I was just writing about what I was going through.”

He hadn’t yet bottomed out. That came when the run-down room he was renting for $50 a month was broken into and his few possessions stolen. Once again, with the loss came the feeling of liberation, that he didn’t have “any expectations or anything to live up to.”

Kris Kristofferson, left, stands during the Country Music Hall of Fame Medallion Ceremony

There was only one way to go, up.

By this time, he had caught on with Columbia Records, not as a performer but studio set-up man. In a tale he enjoyed telling over the years, he said he was essentially a janitor, emptying the ashtrays for the likes of Johnny Cash, Dylan and other performers doing what he wanted to do. It was menial work, but it gave him the chance to pitch his songs to Cash through intermediaries. Cash, he was told, liked the songs but didn’t record any.

Finally, Kristofferson decided to take desperate measures, flying a helicopter to Cash’s home and landing in his backyard. When the singer emerged to see what was going on, Kristofferson handed him a demo tape. “I’d pitched him every song I ever wrote, so he knew who I was,” Kristofferson said in 2008. “But it was still kind of an invasion of privacy that I wouldn’t recommend.”

After four years of struggle, things started breaking his way. Ray Price had a hit with “For the Good Times,” and Cash followed with “Sunday Morning Coming Down.” When Sammi Smith’s version of “Help Me Make It Through the Night” surged up the charts, followed by his own “Loving Her Was Easier (Than Anything I’ll Ever Do Again),” Kristofferson became the hottest songwriter in Nashville.

“Within a matter of months, I had gone from being a guy flying helicopters in the Gulf of Mexico to suddenly performing in front of half a million people,” he said. “But fortunately, I didn’t know any better.”

While providing material for others, he was now singing his own songs. He would always be self-deprecating about his voice. “I can’t play the guitar that well, and I certainly can’t sing that well — but better than Willie Nelson says I can,” he once said with a laugh.

His voice might have been raw and raspy, but it was also expressive and rich, a fitting accompaniment to his introspective songs. One critic compared it to the “grit and softness of ancient stone, worn smooth by time and elements.”

“Me and Bobby McGee,” his best-known song, became a virtual anthem for the 1970s when Janis Joplin recorded it. Kristofferson had stayed at her home in Los Angeles but never heard her version of the song until the day after she died of a drug overdose, in October 1970.

Country singers Taylor Swift and Kris Kristofferson take a photo together.

“She was real funny, and real smart. And a real feeling person,” he recalled. “It’s funny that she was only 27 when she died. She was only a little girl, skipping around the house in high heels and feathers.” When he sang the song in concerts, he often concluded with a soft, “for Janis.”

He chronicled his own battle with substance abuse in his most confessional song, “Pilgrim, Chapter 33.”

“He’s a pilgrim and a preacher, and a problem when he’s stoned / He’s a walkin’ contradiction, partly truth and partly fiction.”

He was not unfamiliar with alcohol. But now, as fame came his way, the recreational habit exploded into a two-bottles-of-whiskey-a-day booze soak. Always unsure of his talent, alcohol coddled and helped him feel “handsome and bulletproof.”

Somehow, he kept his professional commitments, which only increased when the movies came calling. There was something about what one reviewer called his “power-drill eyes and lawn mower voice” that was made for the big screen’s obsession in the 1970s with burned-out, shaggy-haired rockers. First came “Cisco Pike,” about a fading musician who turns to drug dealing, and then Streisand’s remake of “A Star Is Born,” which made him a sex symbol.

“I don’t care what he sings about, I just came to look at him,” a woman from Newport Beach said in 1987, when he was in his activist period, putting out albums such as “Third World Warrior.”

In the first flush of movie fame, however, he seemed intent on living up to the caricature of the overindulged celebrity with a rampaging ego. On the set of “A Star Is Born,” he was known as Kris Pissed-off-erson.

His relationship with singer Rita Coolidge, his second wife, was already in trouble when he ventured into forbidden territory for mainstream actors and posed naked in Playboy with Sarah Myles, his co-star in “The Sailor Who Fell From Grace With the Sea.” Now, with fans shoving the pictures in his wife’s face for autographs, their backstage fights on the road left him “morbid and suicidal,” he said.

Singer Kris Kristofferson performs at the Glastonbury music festival at Worthy Farm in 2017.

If 1970 was the year Kris Kristofferson, songwriter, entertainer, philosopher, took flight, exactly a decade later was when he got his wings clipped. First came a divorce from Coolidge, then his starring role in the disastrous western epic “Heaven’s Gate.” The role should have crowned his career. Instead, it nearly destroyed it. The movie was savaged by critics and bankrupted United Artists. Kristofferson’s reputation was in “the dumpster for years” afterward, he said, more bemused than bitter.

Fame and money had never been a driving force. Doing what he wanted, freedom, that was the thing. And once the A-list offers stopped coming, he gave up drinking, left behind his enfant terrible reputation, and rediscovered his passion for performing. He went back on the road with his band, the Border Lords, often playing intimate roadhouses rather than big arenas.

When a customer in Bakersfield asked him, “‘What are you doing in this honky-tonk?’ I just told him, ‘It’s better than being a janitor.’”

“Kris doesn’t even know what the word ‘commercial’ means,” said friend and screenwriter Bud Shrake. “He could have had a totally different kind of career if he’d wanted to go on stage performing ‘Me and Bobby McGee’ every night. He could have made a fortune. Instead, he goes on the road, and the audience might hear 25 songs about the Sandinista revolution.”

Meyers was a Pepperdine University law student when she and Kristofferson met at a gym in Los Angeles. After they married in 1983 he became a father again, this time finding joy in it. Family “is the best part of my life right now,” he said in 2006. Home was in Maui, not far from Nelson, a golfing partner.

Nelson was responsible for one of Kristofferson’s career highlights, becoming a part of the country music super-group the Highwaymen, with Nelson, Cash and Waylon Jennings. When they invited Kristofferson in, he said he felt like “a little kid who had climbed up on Mt. Rushmore and stuck his face up there.”

With age came health problems. In 1999, he had triple heart bypass surgery. In his late 70s, his memory problems were so serious that doctors put him on Alzheimer‘s drugs. It turned out he had contracted Lyme disease on a movie set in a Vermont forest. When the depression and Alzheimer’s medications were removed, “All of a sudden he was back,” his wife said.

He still had memory difficulties, but Kristofferson was among the least worried of his family about his declining mental acuity. “I really have no anxiety about controlling my own life,” he said in 2016. “Somehow, I just slipped into it and it’s worked.”

He retired from performing in 2020, at 83.

Reflecting earlier on his career, Kris Kristofferson said he felt “that I and many of the people I admire are figments of our own imagination. When I think back to when I was writing my first songs, like when I was 11 years old down in Brownsville, Texas, I think that I imagined myself into a pretty full life after that.”

Kristofferson is survived by his wife, Lisa; eight children, Tracy, Kris Jr., Casey, Jesse, Jody, John, Kelly and Blake; and seven grandchildren.

Johnson is a former Times staff writer.