Kris Kristofferson, Country Songwriting Legend and Celebrated Actor, Dies at 88

Kris Kristofferson, a Rhodes scholar with a deft writing style and rough charisma who became a country music superstar and A-list Hollywood actor, has died.

Kristofferson died at his home in Maui, Hawaii, on Saturday (Sept. 28), spokeswoman Ebie McFarland said in an email to Billboard. He was 88.

McFarland said Kristofferson died peacefully, surrounded by his family. No cause was given. He was 88.

Starting in the late 1960s, the Brownsville, Texas, native wrote such classics 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.

He also starred opposite Ellen Burstyn in director Martin Scorsese’s 1974 film Alice Doesn’t Live Here Anymore, starred opposite Barbra Streisand in the 1976 A Star Is Born and acted alongside Wesley Snipes in Marvel’s Blade in 1998.

On the all-genre Billboard 200 albums chart, Kristofferson notched 19 entries, including the No. 1 soundtrack A Star is Born, in which he co-starred with Streisand. He charted a dozen entries on Billboard’s Hot Country Songs chart, including two No. 1s: “Why Me” in 1973 and the all-star collaboration “Highwayman” in 1985 with Waylon Jennings, Willie Nelson and Johnny Cash. On the Top Country Albums chart, he placed 25 titles, including a trio of No. 1s: Jesus Was a Capricorn (1973), Full Moon (with Rita Coolidge, 1973) and Highwayman (with Nelson, Jennings and Cash, in 1985).

Songs he famously wrote that became hits recorded by other artists include: “Me and Bobby McGee” (No. 1 on the Hot 100 for Janis Joplin), “Sunday Mornin’ Comin’ Down” (No. 1 on Hot Country Songs for Johnny Cash), “For the Good Times” (No. 1 on Hot Country Songs for Ray Price) and “Help Me Make It Through the Night” (No. 1 on Hot Country Songs for Sammi Smith).

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 and bell-bottomed slacks, and his counterculture songs influenced by Bob Dylan, he represented a new breed of country songwriters alongside such peers 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 for Kristofferson held by BMI. “Everything he writes is a standard and we’re all just going to have to live with that.”

As an actor, he played the leading man opposite Barbara Streisand and Ellen Burstyn, but also had a fondness for shoot-out Westerns and cowboy dramas.

He was a Golden Gloves boxer and football player in college, received a master’s degree in English from Merton College at the University of Oxford in England and turned down an appointment to teach at the U.S. 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. Cash liked to tell a mostly exaggerated story of how Kristofferson, a former U.S. 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 that with all respect to Cash, while he did land a helicopter at Cash’s house, the Man in Black wasn’t even home at the time, the demo tape was a song that no one ever actually cut — and he certainly couldn’t 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.”

Among a number of honors Kristofferson received throughout his career were four Grammy Awards: best country song for “Help Me Make It Through the Night” (1971), best country performance by a duo or group for “From the Bottle to the Bottom” with Rita Coolidge (1973) and “Lover Please” with Coolidge (1975), and a Grammy Lifetime Achievement Award (2014).

He took home a CMA Award for “Sunday Mornin’ Comin’ Down” in 1970, won an ACM Award for “Highwayman” in 1985, was inducted into the Country Music Hall of Fame in 2004 and was honored by the Country Music Association with the Willie Nelson Lifetime Achievement Award in 2019. He also earned a Golden Globe for his work in A Star Is Born in 1976.

“The country music world has lost one of its most profound storytellers,” noted Sarah Trahern, Country Music Association CEO, in a statement sent to Billboard following the death of Kristofferson, who had hosted the CMA Awards in 1985 with Anne Murray and in 1986 with Nelson. “I was fortunate to get to work with Kris on many projects over the years. His charm was exactly what you’d expect — unassuming and slightly mysterious, yet deeply warm. As a prolific writer, actor and performer, his gifts were unlike anyone else. We regret that we will no longer be beneficiaries of his incredible words and talents. Our hearts go out to Kris’ friends and family during this sad 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 just days before she died in 1970 from a drug overdose. The recording became a posthumous No. 1 hit for Joplin.

In 1973, Kristofferson married fellow songwriter Rita Coolidge, and together they had a successful duet career that earned them two Grammy awards. They divorced in 1980.

He retired from performing and recording in 2021, making only occasional guest appearances on stage.