Kris Kristofferson, singer-songwriter and actor, has died at the age of 88

Kris Kristofferson, a Rhodes scholar with deft writing and rugged charisma who became a country superstar and star Hollywood actor, has died.

Kristofferson died Saturday at his home in Maui, Hawaii, surrounded by his family, a spokesman said in a statement. He was 88.

Starting in the late 1960s, the Brownsville native wrote classics like “Sunday Mornin’ Comin’ Down” and “Help Me Make it Through the Night.” Kristofferson was a singer himself, but many of his songs became known primarily through being sung by others, be it Ray Price with “For the Good Times” or Janis Joplin with “Me and Bobby McGee.”

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

Kristofferson, who could recite William Blake by heart, wove intricate folk lyrics about loneliness and tender romance into popular country music. With his long hair, bell-bottoms and Bob Dylan-influenced counterculture songs, he represented a new generation of country songwriters alongside colleagues like Willie Nelson, John Prine and Tom T. Hall.

“Kris somehow brought it from the Dark Ages to the present, made it acceptable and brought great lyrics — I mean, the best possible lyrics,” Nelson said in a 1999 segment about Kristofferson on “60 Minutes.” “Simple but profound.”

He was a Golden Gloves boxer and football player in college, received a master’s degree in English from Merton College, Oxford University in England, and turned down a teaching position at the U.S. Military Academy at West Point, New York, to study 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 groundbreaking double album Blonde on Blonde.

At times, the legend of Kristofferson was larger than real life. Johnny Cash liked to tell a largely exaggerated story about how Kristofferson, a former U.S. Army pilot, landed a helicopter on Cash’s lawn with a beer in his hand to give him a cassette of “Sunday Mornin’ Comin’ Down.” Over the years, Kristofferson has said in interviews that, with all due respect to Cash, he had a helicopter land at Cash’s house, but the Man in Black wasn’t even home at the time and the demo tape was a song that no one had actually ever cut and he certainly couldn’t fly a helicopter on a beer.

In an interview with The Associated Press in 2006, he said that without Cash he might not have had a career.

“Shaking his hand backstage at the Grand Ole Opry when I was still in the Army was the moment I decided to come back,” Kristofferson said. “It was electrifying. He kind of took me under his wing before he recorded one of my songs. He recorded my first record, which was record of the year. He brought me on stage for the first time.”

One of his most recorded songs, “Me and Bobby McGee,” was written at the recommendation of Monument Records founder Fred Foster. Foster had a song title in mind called “Me and Bobby McKee,” named after a secretary in his building. Kristofferson said in an interview in Performing Songwriter magazine that he was inspired to write the lyrics about a man and a woman traveling 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 of a drug overdose in 1970. The recording became a posthumous No. 1 hit for Joplin.

Hits Kristofferson recorded include “Why Me,” “Loving Her Was Easier (Than Anything I’ll Ever Do),” “Watch Closely Now,” “Desperados Waiting for a Train,” and “A Song I’ d Like to Sing.” and “Jesus was a Capricorn.”

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

In 2021, he retired from performing and recording, only occasionally appearing on stage as a guest.