R.I.P. Kris Kristofferson, singer, movie star, and icon of Americana

An American superstar unlike any other, Kris Kristofferson, the legendary country western songwriter, performer, and actor, has died. A spokesperson for the family announced that Kristofferson died Saturday at his home in Maui. He was 88.

Few careers are as steeped in legend as Kristofferson’s. He was a fly on the wall who watched Bob Dylan record Blonde On Blonde as a janitor at Columbia Records and landed a helicopter in Johnny Cash’s backyard. But any of the monumental moments of Kristofferson’s career would amount to the greatest moment of any other. Born in Brownsville, Texas, on June 22, 1936, Kristofferson was raised for a career in the military but soon found that no one career could contain him. After the family settled in California, he attended Pomona College and began publishing short stories in The Atlantic. At the same time, his Rugby team appeared in Sports Illustrated, and he was a Golden Gloves amateur boxer. Kristofferson became a Rhodes Scholar and studied literature at Oxford University. After Oxford, he joined the military in 1960, becoming a pilot and reaching the rank of Captain.

He left the military in 1965 and moved to Nashville, working as a janitor and a helicopter pilot for oil rigs. Mopping the floor of Columbia Records, he watched Dylan record Blonde On Blonde and began taking music more seriously. His first album, 1970’s Kristofferson, included his breakthrough song, “Me And Bobby McGee,” which became a no. 1 hit for Janis Joplin. Later that year, Kristofferson put those pilot skills to work and landed a helicopter in Johnny Cash’s backyard to get his attention. Cash decided to record “Sunday Mornin’ Comin’ Down,” and Kristofferson would win Songwriter of the Year at the CMA awards. In 1971, Kristofferson would be nominated for four Grammys, including Song Of The Year and Best Country Song, for “Bobby McGee” and “Help Me Make It Through The Night.”

To say Kristofferson’s recording output was prolific would be an understatement. By the end of the ’70s, he had released over 10 albums, including the soundtrack to A Star Is Born, his 1976 megawatt Blockbuster co-led by Barbra Streisand, which won him a Golden Globe. The soundtrack to A Star Is Born spent six weeks at no. 1 on Billboard. In the mid-’80s, he formed the country music supergroup The Highwayman with Willie Nelson, Johnny Cash, and Waylon Jennings. The quartet released three albums between 1985 and 1995.

Kristofferson’s transition to film was equally charmed. Making his debut in Dennis Hopper’s maniacal Last Movie in 1971, he soon landed his first proper role in Cisco Pike, opposite Gene Hackman, Karen Black, and Harry Dean Stanton. Soon, he began working with legendary Western auteur Sam Peckinpah. He played one of the West’s most iconic outlaws for the director in Pat Garrett And Billy The Kid, Peckinpah’s underrated masterpiece that would become a high watermark of the genre. For his part, as Billy the Kid, Kristofferson weaponizes his natural rockstar charisma to set the template for the modern Western villain, as irresistibly cool as he is sadistically treacherous. Kristofferson continued with Peckinpah on Bring Me The Head Of Alfredo Garcia and Convoy.

“Well, Sam asked me to come down and talk to him. Sam Peckinpah. When I was going up there, it was a little intimidating. He was throwing knives at a little wooden door he had in his office, an old wooden door,” Kristofferson told A.V. Club in 2010. “And he was throwing knives in there, and sticking them. And I don’t know if he was doing that to get my respect or my attention, but anyway, he ended up putting me in it. And geez, he was really one of the directors that I respected the most at the time. It turned out well.”

There was no shortage of luminaries hoping to work with Kristofferson. Paul Mazursky cast him in Blume In Love. For his first major studio work, Martin Scorsese cast him as the love interest in Alice Doesn’t Live Here Anymore. Michael Cimino included Kristofferson in his studio-cratering masterpiece Heaven’s Gate.

As the lines on his face deepened and his gravelly voice grew more hoarse, he aged into a weathered elder statesman in the Blade trilogy. But his most commanding role came as the focal point of John Sayles’ Lone Star, playing a dead sheriff with a shady past. “Kris Kristofferson is not only from Texas; he’s from the border,” Sayles told A.V. Club last year. “He came from a military family. He lived down in the Brownsville area. Matamoros, that area. I’ve never seen him play a really bad guy, but he’s got that voice and that presence.”

There were few things Kris Kristofferson didn’t do in his 88 years. He hosted the 24th episode of Saturday Night Live and sang his hit “Help Me Make It Through The Night” with Miss Piggy on The Muppet Show. Throughout his career, he won four Grammys, including a 2014 Lifetime Achievement Award.

Kristofferson had eight children across three marriages. After divorcing his singer Rita Coolidge, with whom he’d recorded several records, he married Lisa Meyers in 1983. He is survived by Meyers, his eight children, and seven grandchildren.