Kris Kristofferson, the country music superstar and A-list Hollywood actor, has died at the age of 88. He died peacefully and surrounded by his family at his home in Maui, Hawaii, on Saturday, family spokeswoman Ebie McFarland said. No cause of death was given but the musician had been suffering from memory loss since he was in his 70s.

Starting in the late 1960s, the Texas native wrote such classics standards as Sunday Mornin’ Comin’ Down, Help Me Make it Through the Night, For The Good Times and Me And Bobby McGee. Kristofferson was a singer himself, but many of his songs were best known as performed by others, whether Ray Price crooning For the Good Times or Janis Joplin belting out Me And Bobby McGee.

Kristofferson, who could recite William Blake from memory, wove intricate folk music lyrics about loneliness and tender romance into popular country music. With his long hair, bell-bottomed trousers and counterculture songs influenced by Bob Dylan, he represented a new breed of country songwriters along with peers such as Willie Nelson, John Prine and Tom T Hall.

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

As an actor, Kristofferson played the leading man opposite Barbara Streisand and Ellen Burstyn, but also had a fondness for shoot-out westerns and cowboy dramas. He received a Golden Globe Award for Best Actor for 1976 romantic drama A Star Is Born.

He was a Golden Gloves boxer and American football player in college, received a master’s degree in English from Merton College at the University of Oxford, and turned down an appointment to teach at the US Military Academy at West Point, New York, to pursue songwriting in Nashville.

Hoping to break into the industry, he worked as a part-time janitor at Columbia Records’ Music Row studio in 1966 when Dylan recorded tracks for the seminal Blonde On Blonde double album.

At times, the legend of Kristofferson was larger than real life. Johnny Cash liked to tell a mostly exaggerated story of how Kristofferson, a former US Army pilot, landed a helicopter on Cash’s lawn to give him a tape of Sunday Mornin’ Comin’ Down with a beer in one hand.

Over the years in interviews, Kristofferson said he did land a helicopter at Cash’s house, but the Man in Black was not at home at the time, the demo tape was a song that no one ever actually cut, and he certainly could not fly a helicopter holding a beer. In a 2006 interview with the Associated Press, he said he might not have had a career without Cash.

“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 said. “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 recorded songs, Me And Bobby McGee, was written based on a recommendation from Monument Records founder Fred Foster. Foster had a song title in his head called Me And Bobby McKee, named after a female secretary in his building. Kristofferson said in an interview in the magazine Performing Songwriter that he was inspired to write the lyrics about a man and woman on the road together after watching the Frederico Fellini film La Strada.

Joplin, who had a close relationship with Kristofferson, changed the lyrics to make Bobby McGee a man and cut her version days before she died in 1970 from a drug overdose. The recording became a posthumous number one hit for Joplin.

Hits recorded by Kristofferson 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 married fellow songwriter Rita Coolidge and they had a successful duet career that earned them two Grammy awards. They divorced in 1980.

In the mid-1980s he joined forces with Willie Nelson, Johnny Cash and Waylon Jennings to create the country supergroup The Highwaymen, releasing three albums before all four returned to their solo careers. Former bandmate Nelson said there was “no better songwriter alive” when talking about Kristofferson during a 2009 awards ceremony.

“Everything he writes is a standard and we’re all just going to have to live with that,” Nelson said. Kristofferson won a Grammy Award for hit Help Me Make It Through The Night and was inducted into the county music hall of fame in 2004.

As an actor, he won the 1976 Golden Globe Award for best actor after his performance in romantic drama A Star Is Born opposite Barbra Streisand. The film was a remake of the 1937 original with Janet Gaynor and Fredric March, and was later adapted into a musical starring Judy Garland and James Mason - and subsequently again in 2018 starring Lady Gaga and Bradley Cooper.

Kristofferson also appeared opposite Ellen Burstyn in Martin Scorsese’s 1974 film Alice Doesn’t Live Here Anymore and alongside Wesley Snipes in Marvel’s Blade in 1998.

From Caretaker to Hitmaker

Before the stage and screen, Kristofferson was a boxer with US organisation Golden Gloves, he also gained a master’s degree in English at the University of Oxford, later turning down an opportunity to teach at a US military academy in New York to pursue songwriting in Nashville. Hoping for a break into the industry, he worked as a part-time caretaker at Columbia Records’ Music Row studio.

Kristofferson's legacy will forever be etched in the annals of country music and film. His songs, performed by himself and a constellation of legendary artists, continue to resonate with audiences across generations. His acting career, marked by powerful performances and a captivating presence on screen, further cemented his place in entertainment history. He was a true creative force, leaving behind a treasure trove of music and film that will continue to inspire for years to come. Kristofferson's death marks the end of an era, but his music and film will continue to live on, ensuring his name remains synonymous with excellence in both country music and Hollywood.