Kris Kristofferson, the legendary country singer and acclaimed actor, died peacefully in his home in Maui, Hawaii, on Sept. 28 at age 88, Entertainment Weekly has confirmed. No cause of death was given.

Kristofferson’s career in music and film spanned over half a century, releasing 18 studio albums and appearing in dozens of theatrical and television movies between the 1970s and the 2010s. He won three competitive Grammys from 13 nominations and was also nominated for an Academy Award and won a Golden Globe. His gravelly voice and complex, poetic lyricism made him a favorite among his contemporaries.

Born in Brownsville, Texas, in 1936, Kristofferson’s creative career began as a literature student at Pomona College, where he wrote essays that The Atlantic Monthly published. During college, he also competed in rugby, football, and track and field, for which he was recognized in Sports Illustrated in 1958. The same year, he received a Rhodes Scholarship and attended Oxford University, where he studied poetry, became an accomplished boxer, and wrote some of his earliest songs. After earning his Master’s in 1960, Kristofferson joined the U.S. Army and became a helicopter pilot, and formed a band while stationed in West Germany.

He left the Army in 1965 (much to his family’s chagrin), and moved to Nashville, where he worked as a janitor at Columbia Recording Studios while writing songs. There Kristofferson met June Carter, whom he gave a demo tape of his music to pass along to her husband Johnny Cash. After weeks without a reply, Kristofferson landed a helicopter in Cash’s yard to get his attention.

Kristofferson wrote songs that became moderate hits for other performers, including Dave Dudley, Ray Stevens, Jerry Lee Lewis, and, eventually, Cash. He signed to Epic Records in 1967, and, later, Monument Records, where he released his debut album in 1970, titled Kristofferson. Though the album wasn’t an immediate success, Kristofferson won the Songwriter of the Year award from the CMA Awards, and Kristofferson gained popularity with a 1971 rerelease under a new title, Me and Bobby McGee.

That rerelease came after Kristofferson’s ex-girlfriend, Janis Joplin, recorded his song “Me and Bobby McGee” for her album Pearl, which was released posthumously. Joplin’s version of the song hit No. 1 on the charts, launching Kristofferson to a new stratosphere of success, writing songs for Joe Simon, Bobby Bare, Kenny Rogers, and more. The singer also won his first Grammy in 1971, with “Help Me Make It Through the Night” winning Best Country Song. 

Though he released several albums in the 1970s, he spent the later part of the decade launching his acting career. His unique balance of ruggedness and sensitivity made him a beloved performer in both leading and supporting roles. Making his film debut with a brief part in Dennis Hopper’s The Last Movie in 1971, Kristofferson was cast in his first leading role for the 1972 drama Cisco Pike, followed up with several roles including the titular outlaw in Sam Peckinpah’s Pat Garrett and Billy the Kid, opposite James Coburn and a supporting role in Peckinpah’s 1974 film Bring Me the Head of Alfredo Garcia.

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One of Kristofferson’s most acclaimed performances was in Martin Scorsese’s Alice Doesn’t Live Here Anymore, released in 1974. The singer’s character is the final love interest for Ellen Burstyn’s Alice, providing a tumultuous yet passionate romance for the central heroine in the latter half of the movie.

But his best known role came in 1976, the second remake of A Star Is Born, starring with Barbra Streisand. The film was the second-highest grossing movie of the year behind Rocky, and won Kristofferson a Golden Globe for Best Actor. The film’s soundtrack was also an enormous success, selling nearly 15 million copies worldwide and winning an Oscar and a Grammy. 

He married singer Rita Coolidge in 1973, and their album Full Moon released the same year became a huge hit. They released another album, Breakaway, the following year, and a third, Natural Act, in 1978, before their divorce in 1980. Their collaborations won two Grammys for Best Country Performance by a Duo or Group. 

In 1982, Dolly Parton, Willie Nelson, and Brenda Lee teamed up with Kristofferson for the 20-track collaboration album The Winning Hand. He joined Nelson in the 1984 movie Songwriter, for which Kristofferson was nominated for an Oscar for Best Original Song Score. Nelson and Kristofferson’s soundtrack album Music from Songwriter was a sizable success.

Kristofferson’s most prominent musical collaboration came with The Highwaymen, a supergroup that also featured Johnny Cash, Waylon Jennings, and Nelson. The group released three albums between 1985 and 1995, and also appeared together in the 1986 movie Stagecoach.

An inductee into the Nashville Hall of Fame in 1977, Kristofferson was added to the Songwriters Hall of Fame in 1985, and the Country Music Hall of Fame in 2004. He also received a Lifetime Achievement Award from the Grammys in 2014, as well as the Lifetime Achievement Award from the CMA Awards in 2019.

He continued recording and performing music until 2020, and announced his retirement in 2021. Kristofferson’s film career also includes major films like Heaven’s Gate, Flashpoint, Millennium, Lone Star, the Blade trilogy, Tim Burton’s Planet of the Apes, and the Dolphin Tale duology.

He is survived by his wife Lisa Meyers, eight children, and seven grandchildren.

“We’re all so blessed for our time with him,” his family said in a statement. “Thank you for loving him all these many years, and when you see a rainbow, know he’s smiling down at us all.”