Kris Kristofferson, a Rhodes scholar, was set to be a pillar of the establishment before dropping out to pursue country music. The singer’s greatest hits came from the years he spent as a struggling songwriter chronicling messy, itinerant lives.
In 2017, when he was a mere 81, Kris Kristofferson made his Glastonbury debut. “I know I’m supposed to end this song, but I can’t remember how,” said one of country music’s greatest rebel figures, before a croaked, senior moment-interrupted version of Help Me Make It Through the Night.
Playing on the Pyramid Stage on a sunny Sunday afternoon, Kristofferson did seem a bit doddery, and yet you couldn’t help but be captivated by his quiet authority. And it wasn’t just those of us in the audience who were taken by the performance of this legendary figure.
It took a moment to realise that it was Johnny Depp on guitar, accompanying Kristofferson on his regret-soaked hangover ballad Sunday Mornin’ Comin’ Down. Watching in the wings, meanwhile, was Brad Pitt. For Hollywood superstars, Kristofferson was a figure to aspire to; an embodiment of the great American life.
Starring opposite Barbra Streisand in A Star is Born
The Kristofferson that fascinates me, however, is the one that was developing long before A Star Is Born made him world famous: an aspiring, struggling songwriter who rejected the middle-class path laid out for him in favour of chronicling messy, itinerant lives, in lyrics that matched John Steinbeck for their evocation of the dusty, spacious, imperfect American experience.
And his early struggles were made more poignant by the fact that Kristofferson should have been the golden boy. The son of a Second World War army general, he went to Merton College in Oxford as a Rhodes scholar after displaying an unusual gift for literature. He excelled in boxing and rugby. He returned to the US to join the army, became a captain. He was going to be a pillar of the establishment. Then it all went wrong.
Like a real-life version of Jack Nicholson’s privileged piano prodigy who becomes a rootless oil rig worker in Five Easy Pieces, Kristofferson became a dropout, slumming it in the blue-collar world of country music.
With two children to support, he got a job sweeping floors at Columbia Recording Studios in Nashville, wrote songs of exquisite despair, and spent years being rejected everywhere.
Legend has it that the career break came after he landed in Johnny Cash’s garden via helicopter — a spell as a helicopter pilot off the Gulf of Mexico ended after he was sacked for being drunk at the controls — with a beer in one hand and a tape of his songs in the other. Sufficiently impressed, Cash agreed to record Sunday Mornin’ Comin’ Down. It led to Kristofferson becoming songwriter of the year at the 1970 Country Music Awards.
Kristofferson’s best material came from an intense, desperate two-year period before that accolade, when he was writing furiously between janitorial and helicopter pilot stints and capturing both the frustration and bleak romance a lack of success brings.
Me And Bobby McGee, with its famous line on freedom being another word for having nothing left to lose, came to him after a spell in jail for failing to pay child support. Gettin’ by, High and Strange reflected Kristofferson’s wild ways on the road at early gigs, although in reality he was not the hardened cowboy of legend; more an educated, erudite former Rhodes scholar with the literary power to document his experiences, and those of the people he met, in everyday American vernacular.
Kristofferson went on to play versions of himself as the archetypal hippie cowboy: a drifter in Dennis Hopper’s The Last Movie, a drug-dealing singer in Cisco Pike and, most famously, a sozzled has-been in A Star Is Born.
However, the essence of the man is to be found in those songs he wrote from 1968 to 1970, which revealed the image of the Bukowski-esque barfly he aspired to be and the thoughtful observant writer he actually was. No wonder Depp and Pitt held him with such admiration: they knew a fellow troubled soul and would-be outlaw when they saw one.
Kris Kristofferson’s best songs
Me and Bobby McGee (1971)
Although first recorded by Roger Miller, this became Janis Joplin’s anthem: a tale of two drifters passing through America that became an ode to itinerant hippie freedom as well as a warning of its limitations. Inspiration came from a scene in Fellini’s La Strada when a war-torn Anthony Quinn breaks down on a beach, sobbing.
Help Me Make It Through the Night (1970)
One of the most romantic songs about a one-night stand, this has been covered by everyone from Elvis Presley to Joan Baez, although the most famous version is by the Nashville country star Sammi Smith. Kristofferson was inspired after reading Frank Sinatra’s reply, when asked about his religious beliefs: “Booze, broads or a Bible … whatever helps me make it through the night.”
Sunday Mornin’ Comin’ Down (1969)
Johnny Cash made this alcoholic lament his own, finding in it a paean to the drifter’s life and a sympathy for the plight of the poverty-stricken itinerant. “The beer I had for breakfast wasn’t bad” is a line to remember when the drinking really gets out of hand.
Rita Coolidge and Kristofferson performing in 1979
Please Don’t Tell Me How The Story Ends (1971)
Kristofferson really knew how to bring out the sadness of a short-lived love affair; a classic country staple. “Just let me enjoy it till it’s over,” he pleads. His 1978 duet of it with Rita Coolidge, which came out two years before their divorce, is heartbreaking.
The Silver Tongued Devil and I (1971)
This classic tale of barroom trysts came from Kristofferson’s experiences of working in the Tally-Ho tavern in Nashville; of finding his natural shyness being conquered after a few drinks and the guilt that came with the morning after. It was also the title track of his breakthrough album.
Will Hodgkinson
Originally published Monday September 30 2024, 1.30pm BST, The Times