Kris Kristofferson, the country singer who skillfully combined a prolific acting career with his music, has died at the age of 88.

Kristofferson’s family confirmed his death Sunday evening, saying he “passed away peacefully” on Saturday. “We are all so blessed for our time with him,” read the statement, which was signed by his wife Lisa, his eight children and seven grandchildren. “Thank you for loving him all these years, and when you see a rainbow, know that he is smiling at us all.”

Admired for the daring, emotional vulnerability and literary craft of his country songwriting, Kristofferson regularly topped the US country charts and cover versions of his songs were hits for artists such as Janis Joplin, Gladys Knight and Johnny Cash. In the mid-1970s, he worked with film directors such as Martin Scorsese and Sam Peckinpah, and won a Golden Globe for his work opposite Barbra Streisand in the 1976 remake of A Star is Born.

Born in 1936 in Texas, Kristofferson attended high school in California and initially wanted to become a novelist, later studying literature at Pomona College in Southern California and at Oxford University as a Rhodes Scholar. Inspired by the emerging rock and roll scene, his first foray into music took place in Britain as Kris Carson, although the songs he recorded were never released.

He continued making music during a stint in the US Army, where he became a helicopter pilot, a skill he continued (in the oil industry and the National Guard) after leaving the armed forces in 1965 – which angered his military family. “I prided myself on being the best worker or the man who could dig the ditches the fastest,” he said later. “Something inside me made me want to do the hard things… Part of it was that I wanted to be a writer, and I thought I had to get out and live.”

He moved to the country music hub of Nashville, where he worked as a bartender and as a janitor for Columbia Recording Studios. In the late 1960s he wrote songs for Jerry Lee Lewis and country singers such as Ray Stevens, Faron Young and Billy Walker, but his solo career faltered.

A breakthrough came after he landed a National Guard helicopter at Johnny Cash’s house and presented him with a tape of his songs, later describing the incident as “some kind of invasion of privacy that I wouldn’t recommend “. Cash admired Sunday Mornin’ Comin’ Down and his recording of Kristofferson’s song topped the country charts in 1970 and won song of the year at the Country Music Association Awards.

That year, Kristofferson recorded the first of 18 studio albums he would release during his career. He had a brief relationship with Janis Joplin, who recorded his song Me and Bobby McGee, and it became a No. 1 hit after her death in 1970. Another Kristofferson song from that year, Help Me Make It Through the Night, was a hit single for Sammi Smith. and was later covered by Elvis Presley, Gladys Knight, Mariah Carey and others.

By the time his fourth album Jesus Was a Capricorn topped the country charts in 1972, the strikingly handsome Kristofferson had embarked on an acting career, first appearing in Dennis Hopper’s The Last Movie. Other notable films include playing the outlaw Billy the Kid in Sam Peckinpah’s Pat Garrett and Billy the Kid (1973), opposite Ellen Burstyn in Martin Scorsese’s Alice Doesn’t Live Here Anymore (1974) and with Burt Reynolds in the sports comedy -drama Semi-Difficult (1977). A Star Is Born cemented its success in Hollywood, but was later undermined by Heaven’s Gate (1980), a famous box office flop.

In 1979, Willie Nelson made a hit album of Kristofferson covers, and in 1982 the pair collaborated with Dolly Parton and Brenda Lee on a compilation of their mid-’60s songs. In 1985, Kristofferson and Nelson formed another supergroup, the Highwaymen, with Johnny Cash and Waylon Jennings. Their debut album, Highwayman, with the title track written by Jimmy Webb, returned Kristofferson to the top of the country charts.

In the 1980s, he was an outspoken critic of US President Ronald Reagan and foreign policy in Central America, when the US financed the fight against left-wing forces in El Salvador and Nicaragua. Kristofferson’s 1986 album Repossessed referenced the conflicts.

His acting career, while consistent, was boosted in 1996 by playing the villainous sheriff Charlie Wade in John Sayles’ critically acclaimed neo-western Lone Star alongside Chris Cooper and Matthew McConaughey. It led to prominent roles, including as vampire hunter Abraham Whistler in three Blade films, starring Wesley Snipes.

Kristofferson retired in 2021. His last film role was in the Ethan Hawke-directed drama Blaze (2018), and his most recent album was 2016’s The Cedar Creek Sessions.

He married three times, first to Fran Beer in 1960. He married singer Rita Coolidge in 1973, and their duets album that year, Full Moon, became one of Kristofferson’s biggest hits, reaching the Top 30 of the charts. in 1980. He is survived by his third wife, Lisa Meyers, whom he married in 1983 and had five children, in addition to three other children from his first two marriages.