Kris Kristofferson’s pre-fame years tell a story you couldn’t make up. Born in Texas in 1936, the son of a Swedish immigrant, he got the creative writing bug early and studied it at Pomona College (where David Foster Wallace would go on to teach a couple of generations later). He went to Oxford on a Rhodes Scholarship to study William Blake. One reckons that more than one scholarly paper has been written drawing a line from Blake to Kristofferson’s own musical observation that “Freedom’s just another word for nothing left to lose.” After that, a stint in the Army, where he learned to fly a helicopter and also rose to the rank of captain. Eventually intent on expressing himself in song, he decamped with his young family — he married a home-town sweetheart while on break from school and had a couple of children early on — to Nashville. Sweeping floors at a Columbia Records studio, he chanced upon one of his idols, Bob Dylan, when the latter pitched a tent there to record the epochal album Blonde on Blonde. He once landed a chopper on Johnny Cash’s lawn to get the signing legend’s attention. 

Kristofferson’s own work at the time was more in line with pre-counterculture C&W. Hangover songs and infidelity songs, and pretty hard stuff  — “Sunday Morning Coming Down,” “For The Good Times.”  But he leaned more toward the counterculture personally, and, and by the time he made his second album, The Silver-Tongued Devil And I, he was also hanging out with and acting for Hollywood hellion Dennis Hopper, who cast Kristofferson in one of the many allegorical roles contained in his apocalyptic allegory The Last Movie. Not quite a mainstream success (it was in fact highly reviled and despite critical reappraisal is still looked at with disdain by large portions of moviedom), it got him in the door of acting, and his blue eyes, naturally laid-back manner, and confident physicality made him a screen natural. He played the lead in Cisco Pike, a drug-running picture in which he squared off against a corrupt cop played by Gene Hackman, and more than held his own.  

Soon followed one of his most iconic roles, that of Billy in 1973’s Pat Garrett and Billy the Kid, a poetic revisionist Western directed by Sam Peckinpah. (He had worked for Peckinpah a little before, in Bring Me The Head of Alfredo Garcia, as a taciturn rapist biker. Aiiieee.) Despite his reputation as a visionary, which he was, Peckinpah wasn’t an originator. Boasting that he was a “good whore,” the director almost never actually developed the projects he took on, and Garrett came about via conspiratorial meetings between Kristofferson, Dylan (who initially wanted to play Billy himself, but not being to type ended up playing an enigmatic criminal named “Alias”), and screenwriter Rudy Wurlitzer. During the shoot, Kristofferson had to wrest a bottle from his alcoholic director more than once, and the troubles on the movie continued when the production studio mutilated the picture. A recent Criterion edition restores the movie to something of its intended glory. Kristofferson’s Billy is a bit of a self-conscious martyr — on one of his surrenders to the law he strikes a Christ-like pose — and Kristofferson does look iconic, to be sure. (His then-wife, Rita Coolidge, looks for-sure angelic in the small, practically wordless role of Maria, one of Billy’s girls.) He looked slightly less iconic, but still sturdy and confident, in 1978’s Convoy, his last picture with Peckinpah, in which he, the director, and costar Ali McGraw subjected themselves to the indignity of making a film based on a Top 40 novelty hit celebrating the CB radio craze. The messy results are a goofy testament to how seriously any of the participants took it.  

He played a more down to earth character than Billy in 1974’s Alice Doesn’t Live Here Any More, an early Martin Scorsese movie with a theme that’s rare in the maestro’s work: female autonomy. The movie’s title character, a single mom played by Ellen Burstyn, wants to make a better life for herself and her son in the contemporary American West. Kristofferson plays the man who romances her against what she considers her better judgement — despite the fact that he’s clearly a keeper. Recalling their collaboration, Scorsese said:

“[A]t first we kept making each other nervous. In rehearsal he would ask ‘Where do you want me to stand?’ and I would say “I don’t know.’ Then he’d say ‘You’ve got to tell me where to stand.’ The poor guy had just done Pat Garrett and Billy the Kid, which I loved, but a lot of people hated. So one day we went off on our own to rehearse and I kidded him, shouted stupid things and looned around, saying ‘I look funny in front of you and you look funny in front of me. So what? We’ll look funny in front of each other.’ It broke the tension and after that our relationship was great. I had learned something from him.”

Kristofferson’s aforementioned second album, The Silver Tongued Devil And I, played something of a supporting role in Scorsese’s subsequent Taxi Driver, a record Travis attempts to gift to Cybill Shepherd’s Betsy. 

Kristofferson’s work as an actor gave him a new set of performing chops. Reviewing his first, self-titled album, the critic Robert Christgau praised his songs — how could you not? — with a caveat: “But he’s the worst singer I’ve ever heard. It’s not that he’s off key–he has no relation to key. He also has no phrasing, no dynamics, no energy, no authority, no dramatic ability, and no control of the top two-thirds of his six-note range.” Seven years later, the critic backed off a little: “Over the years, Kristofferson has learned enough about acting to challenge George Burns as a crooner […] It’s conceivable he might even do somewhat better now on some of his great early songs.” Interestingly, the country supergroup that reaped a lot of gold records in the ‘70s, The Highwaymen, was made up of country legends who’d all done some movie acting; Johnny Cash, Waylon Jennings, and Willie Nelson. 

Kristofferson delivered the most authentic performance in the 1977 reboot of the Hollywood stalwart A Star Is Born. A passion project for producer-star Barbra Streisand, the unhappy set found him subordinate to her and her ego, and perhaps his disgruntlement fed his hard-bitten work as soon-to-be on the skids rock star John Norman Maine. (The movie was the subject of a hilarious SCTV parody, with Joe Flaherty essaying a Kristofferson who drunkenly extolled the virtues of singing about “critters.”) Streisand herself is too self-conscious to pull of the early naivete of her show-biz-success role, but Kristofferson is immediately electric in his character’s sozzled state. 

The actor carried the controversial 1980 Heaven’s Gate, director Michael Cimino’ epic Western tragedy of American intolerance. He not only gave a great performance as an honest and eventually helpless lawman, he stood up for the embattled picture and its director. Unfortunately, the contemporary bolstering of its reputation means that only the director’s cut is available. The studio mandated theatrical cut is the one in which Kristofferson gives what I consider his greatest line reading: looking across a patch of land at some bad guys, he sees one mooning the general vicinity, and recognizing the guy, sadly drawls “That man is a friend of the President of the United States.” He followed up Gate with 1981’s high-finance thriller Rollover, pairing with another legendary Hollywood leading lady, Jane Fonda. The pair brought the heat, but couldn’t bring the final film to a boil. 

He continued to work with visionary directors, making two pictures with John Sayles, the harrowing 1996 epic Lone Star, and the somewhat more enigmatic 1999 Limbo, in which he played a pilot (and, if I recall correctly, did his own flying). For Altman associate Alan Rudolph he did Trouble In Mind, a fanciful 1985 neo-noir. By the late ‘90s, his acting career had settled into genre: an action picture with Steven Seagal, a couple of Blade pictures, and so on. Early in this century he did a Christmas movie with Willie and latter-day county star Lyle Lovett. Not necessarily fit work for Billy the Kid, but it kept the lights on. 2009 saw him reviving his singing career with the imprimatur of legendary producer of legends Don Was, and he officially, and honorably, retired in 2021. Not before reuniting, cordially, with Streisand, guesting with her in concert across the pond in 2019. In Hyde Park, London…just a 90 minute train ride to Oxford. 

Veteran critic Glenn Kenny reviews‎ new releases at RogerEbert.com, the New York Times, and, as befits someone of his advanced age, the AARP magazine. He blogs, very occasionally, at Some Came Running and tweets, mostly in jest, at @glenn__kenny. He is the author of the The World Is Yours: The Story of Scarface, published by Hanover Square Press, and now available for at a bookstore near you.