Inside Kris Kristofferson's life of heartbreak and wild success as he dies aged 88

Kris Kristofferson once admitted to nearly destroying himself through hard partying because he believed being a serious artist meant “living on the edge” alongside the twin demons of drink and drugs. “I thought all serious artists were self-destructive,” the star, who has died aged 88 at home in Hawaii, once remarked.

“That anybody worth their salt was going to be out there living on the edge.” The country music legend, who was also a Hollywood leading man and admired character actor, was a man of deep contradictions.

He was a thoughtful intellectual who studied literature at Oxford University before joining the US Army and volunteering for Vietnam; a major songwriter whose biggest hits were enjoyed by other people; and an imposing 6ft blue-collar hero yet never happier than when he was discussing poetry. His most famous songs included ‘Me and Bobby McGee’, ‘Sunday Mornin' Comin' Down’, and ‘Help Me Make It Through the Night’ – all of which first became hits for other artists.

Over seven decades, Kristofferson’s career varied wildly between triumph and mediocrity, at times it was almost as if he was deliberately trying to alienate fans. Yet his best films, including playing a troubled rocker in A Star Is Born alongside Barbra Streisand in 1978, for which he won a Golden Globe, were huge box office successes, and his songs, inspired by a love of literature, would transform country music in the seventies when the genre was awash with mediocre tunes and dogged by cliche.

Born in Brownsville, Texas, in 1936, the son of a decorated US Army Major-General who wanted his son to follow in his footsteps and pushed him academically, Kristofferson studied creative literature after the family moved to California, later winning a prestigious Rhodes Scholarship to Merton College, Oxford, to study English literature. He received a blue in boxing and excelled at rugby but was asked to leave one course after arguing furiously with his tutor about William Blake.

He also played the guitar and dreamed of becoming a songwriter. After graduating, he stayed in England to try and forge a music career, performing and writing as Kris Carson in a nod to the US frontiersman Kit Carson.

He secured a deal with the Top Rank Record label and pop impresario Larry Parnes as his manager but, when he failed to become a star, returned to America where he married girlfriend, ‘Fran’ Beer, in 1960, had two children and joined the US Army in swift succession.

Although his father accepted his decision, his mother never entirely forgave him for throwing his career away “to become a bum” and they disowned him.

By now, he was already drinking heavily. But he graduated Airborne School, Ranger School and Flight School, served in Germany during the Cold War and volunteered to go to Vietnam.

He was set to become a Major when he quit the United States Army Rangers in 165 after nearly five years after being offered a teaching role at West Point, the US Army Military Academy, instead of being allowed to fight.

One of his children, he eventually had eight, suffered from a defective oesophagus – which meant Kristofferson needed $100,000 for medical bills – so he moved his family to the coast and took a job as a part-time helicopter pilot serving oil rigs in the Gulf of Mexico.

Having been fired for drinking at work, he moved to Nashville where the family lived in a slum and he worked as a caretaker at a recording studio.

Feeling a failure and drinking heavily, his marriage ended after eight years. He was jailed briefly for failure to pay child support, later recalling: “I felt the freedom then of nothing left to lose. I was a failure, and it was a very liberating thing.”

Despite his lack of success, he was gaining a reputation as a songwriter and eventually persuaded his hero Johnny Cash to record one of his compositions having borrowed a helicopter and landed in Cash’s garden carrying a tape and a beer.

Cash, no slouch himself when it came to hard living, agreed to record Kristofferson’s song, ‘Sunday Mornin’ Comin’ Down’, which had already been recorded by a lesser-known singer, Ray Stevens. It became a hit for Cash and was voted Song of the Year by the Country Music Association in 1970, later being listed at number 476 on Rolling Stone magazine’s Top 500 Best Songs of All Time.

The rival Academy of Country Music chose another of Kristofferson’s songs, ‘For The Good Times’, recorded by Ray Price, as its own song of the year – the only time in country music history in which an artist has taken both awards with different songs.

Finally, at the age of 34, Kristofferson had arrived but it was in the run-up to this time his partying was at its most destructive. He had dated doomed blues star Janis Joplin, and her death from drugs and alcohol in October 1970 aged just 27 hit him badly.

“I don't know what you call a love affair, but we were real close,” he recalled. “I liked her sense of humour. I was doing a lot of drinking then... And she was trying to kick [heroin].”

Joplin would have a number-one hit with ‘Me and Bobby McGee’ from her posthumous album Pearl. Yet Kristofferson continued with his heavy drinking to the point where he was a self-professed “functioning alcoholic”.

“For a couple of years, it was Jack Daniels, then it was tequila, then it was anything,” he admitted. “When I was performing, I couldn't imagine getting up and doing it without drinking.” His stage-fright, eased by self-deprecating jokes and booze, didn’t help.

It was only after seeing his on-screen death in the hit romantic drama A Star Is Born, in which he played a thinly-veiled, self-destructive rock star, John Norman Howard, that he finally found the courage to quit drinking.

It was the scene where co-star Streisand's Esther Hoffman finds John dying in a field after crashing his sports car while drinking and speeding that gave him his wake-up call.

“I remember feeling that that could very easily be my wife and kids crying over me,”' he recalled. “I quit drinking over that. I didn't want to die before my daughter grew up.”

Kristofferson's first film role had been in Dennis Hopper's The Last Movie, in 1971, while he later played the title outlaw in 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. More recently, he won a new generation of fans appearing alongside Wesley Snipes as Whistler in the Blade movies.

Having married the singer Rita Coolidge in 1973, they divorced seven years later after having one child, and Kristofferson married his third and final wife, Lisa Meyers, in 1983. They had five children together.

The four-time Grammy Award winner was inducted into the Country Music Hall of Fame in 2004. While reflecting on how he eventually found a peaceful family life in Maui, Hawaii, the star admitted: “I never could have imagined this.

“I sit right here and think how it could have turned out so differently. I never thought I'd live past 30. I could have ended up dead.”

He finally died surrounded by his family on Saturday.

“It is with a heavy heart that we share the news that our husband/father/grandfather, Kris Kristofferson, passed away peacefully on Saturday, September 28 at home,” his family said in a statement.

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

Streisand said she "knew he was something special" the first time she saw him perform. In A Star Is Born, they sang together Evergreen, which won an Oscar for best original song, and Kristofferson won a Golden Globe for his acting.

Streisand also asked him to appear on stage with her in London's Hyde Park in 2019. "He was as charming as ever, and the audience showered him with applause. It was a joy seeing him receive the recognition and love he so richly deserved,” she wrote yesterday.

Words by Matt Nixon.