Kris Kristofferson, the country music legend who went on to enjoy an A-list successful Hollywood acting career, has died at the age of 88

Kris Kristofferson performs at Drammen Teater on June 2, 2019 in Drammen, Norway (Image: Redferns)

Country music legend and Hollywood actor Kris Kristofferson has passed away.

The Brownsville, Texas-born star, who won a Golden Globe for his role in the 1976 film A Star is Born alongside Barbara Streisand, was not only a gifted actor but also a celebrated country music artist. He bagged four Grammy awards, including a lifetime achievement award in 2014.

Kristofferson breathed his last at his home in Maui, Hawaii on Saturday, according to family spokeswoman Ebie McFarland. The 88 year old died peacefully, surrounded by his loved ones. The cause of death has not been disclosed.

From the late 1960s, Kristofferson penned classic hits such as Sunday Mornin’ Comin’ Down, Help Me Make it Through the Night, For the Good Times and Me and Bobby McGee. While he was a singer himself, many of his songs gained fame through performances by other artists, like Ray Price’s rendition of For the Good Times or Janis Joplin’s powerful performance of Me and Bobby McGee.

In 2004, Kristofferson was inducted into the Country Music Hall of Fame. The chief executive for the Country Music Hall of Fame, Kyle Young, said: “Kris Kristofferson believed creativity is God-given, and those who ignore such a gift are doomed to unhappiness. He preached that a life of the mind gives voice to the soul, and his work gave voice not only to his soul but to ours. He leaves a resounding legacy.

Kris Kristofferson in Heaven’s Gate (Image: United Artists)

In addition to his musical career, Kristofferson made a name for himself in Hollywood, starring in films like Martin Scorsese’s 1974 film Alice Doesn’t Live Here Anymore, A Star Is Born with Streisand, and Marvel’s Blade in 1998 alongside Wesley Snipes.

Kristofferson, a man who could recite William Blake’s poetry by heart, was known for his intricate folk music lyrics that beautifully captured themes of loneliness and tender romance. His long hair, bell-bottomed trousers, and counterculture songs influenced by Bob Dylan marked him as part of a new wave of country songwriters, alongside contemporaries like Willie Nelson, John Prine, and Tom T Hall.

“There’s no better songwriter alive than Kris Kristofferson,” Nelson declared at a November 2009 award ceremony held by BMI in honour of Kristofferson. “Everything he writes is a standard and we’re all just going to have to live with that.”

Before his music career took off, Kristofferson was a Golden Gloves boxer and college football player. He earned a master’s degree in English from Merton College at the University of Oxford and even turned down a teaching position at the US Military Academy at West Point, New York, to chase his dream of songwriting in Nashville.

Musician and actor Kris Kristofferson shakes hands with the Rev Jesse Jackson (not seen) at a memorial service for the late boxe (Image: Reuters)

In an attempt to break into the industry, he worked part-time as a janitor at Columbia Records’ Music Row studio in 1966, during which time Dylan recorded tracks for the iconic Blonde on Blonde double album.

The legend of Kristofferson often seemed larger than life itself. Johnny Cash was fond of recounting a somewhat embellished tale about how Kristofferson, an ex-US Army pilot, landed a helicopter on Cash’s lawn to hand him a demo tape of Sunday Mornin’ Comin’ Down, beer in hand.

However, Kristofferson clarified in various interviews over the years that while he did indeed land a helicopter at Cash’s residence, the Man in Black wasn’t even home at the time. The demo tape was for a song that never got cut, and he certainly couldn’t have flown a helicopter whilst holding a beer.

In a 2006 interview, Kristofferson acknowledged that his career might not have taken off without Cash’s influence.

Rocking out on A Star Is Born with Barbara Streisand (Image: REX)

“Shaking his hand when I was still in the Army backstage at the Grand Ole Opry was the moment I’d decided I’d come back,” Kristofferson revealed. “It was electric. He kind of took me under his wing before he cut any of my songs. He cut my first record that was record of the year. He put me on stage the first time.”

One of his most covered songs, Me and Bobby McGee, came about due to a suggestion from Monument Records founder Fred Foster. Foster had a song title in mind, Me and Bobby McKee, named after a female secretary in his building.

In an interview with Performing Songwriter magazine, Kristofferson explained that he was inspired to pen the lyrics about a man and woman journeying together after watching the Frederico Fellini film, La Strada.

Joplin, who shared a close bond with Kristofferson, altered the lyrics to portray Bobby McGee as a male character and recorded her version just days before her untimely death in 1970 due to a drug overdose. The track posthumously soared to No.

With Streisand in A Star is Born (Image: FilmPublicityArchive/United Archives via Getty Images)

1 for Joplin. Some of Kristofferson’s notable recordings include “Why Me”, “Loving Her Was Easier (Than Anything I’ll Ever Do)”, “Watch Closely Now”, “Desperados Waiting for a Train”, “A Song I’d Like to Sing” and “Jesus Was a Capricorn”.

In 1973, he tied the knot with fellow songwriter Rita Coolidge and their successful duet career bagged them two Grammy awards. However, they parted ways in 1980.

He bid adieu to performing and recording in 2021, only making sporadic guest appearances on stage, including a performance with Roseanne Cash at Nelson’s 90th birthday celebration at the Hollywood Bowl in Los Angeles in 2023. The two sang a song Kristofferson wrote and Nelson – one of the great interpreters of his work – recorded the best-known version of.

Nelson and Kristofferson would join forces with Johnny Cash and Waylon Jennings to create the country supergroup “The Highwaymen” starting in the mid-1980s.

The formation of the Highwaymen, with Nelson, Cash and Jennings, was another pivotal point in his career as a performer.

“I think I was different from the other guys in that I came in it as a fan of all of them,” Kristofferson said in 2005. “I had a respect for them when I was still in the Army. When I went to Nashville they were like major heroes of mine because they were people who took the music seriously. To be not only recorded by them but to be friends with them and to work side by side was just a little unreal. It was like seeing your face on Mount Rushmore.”

The group put out just three albums between 1985 and 1995 before the singers returned to their solo careers. Jennings died in 2002 and Cash died a year later. Kristofferson said in 2005 that there was some talk about reforming the group with other artists, such as George Jones or Hank Williams Jr., but Kristofferson said it wouldn’t have been the same.

“When I look back now – I know I hear Willie say it was the best time of his life,” Kristofferson said in 2005. “For me, I wish I was more aware how short of a time it would be. It was several years, but it was still like the blink of an eye. I wish I would have cherished each moment.”

His sharp-tongued political lyrics sometimes hurt his popularity, especially in the late 1980s. His 1989 album, “Third World Warrior” was focused on Central America and what United States policy had wrought there, but critics and fans weren’t excited about the overtly political songs.

He said during a 1995 interview he remembered a woman complaining about one of the songs that began with killing babies in the name of freedom. “And I said, `Well, what made you mad – the fact that I was saying it or the fact that we’re doing it? To me, they were getting mad at me ’cause I was telling them what was going on.”

As the son of an Air Force General, he enlisted in the Army in the 1960s because it was expected of him. “I was in ROTC in college, and it was just taken for granted in my family that I’d do my service,” he said in a 2006 interview. “From my background and the generation I came up in, honor and serving your country were just taken for granted. So, later, when you come to question some of the things being done in your name, it was particularly painful.”

Hollywood may have saved his music career. He still got exposure through his film and television appearances even when he couldn’t afford to tour with a full band.
Kristofferson’s first role was in Dennis Hopper’s “The Last Movie,” in 1971.

He had a fondness for Westerns, and would use his gravelly voice to play attractive, stoic leading men. He was Burstyn’s ruggedly handsome love interest in Alice Doesn’t Live Here Anymore and a tragic rock star in a rocky relationship with Streisand in A Star Is Born, a role echoed by Bradley Cooper in the 2018 remake.

He was the young title outlaw in director Sam Peckinpah’s 1973 Pat Garrett and Billy the Kid, a truck driver for the same director in 1978’s Convoy, and a corrupt sheriff in director John Sayles’ 1996, Lone Star. He also starred in one of Hollywood biggest financial flops, Heaven’s Gate, a 1980 Western that ran tens of millions of dollars over budget.

And in a rare appearance in a superhero movie, he played the mentor of Snipes’ vampire hunter in Blade. He described in how he got his first acting gigs when he performed in Los Angeles.

“It just happened that my first professional gig was at the Troubadour in L.A. opening for Linda Rondstadt,” Kristofferson said. “Robert Hilburn (Los Angeles Times music critic) wrote a fantastic review and the concert was held over for a week,” Kristofferson said. “There were a bunch of movie people coming in there, and I started getting film offers with no experience. Of course, I had no experience performing either.”