Kris Kristofferson, who earned acclaim as a singer, songwriter and actor during a career that spanned six decades, died Saturday (9/28) at his home in Maui. He was 88.

The native of Brownsville, Texas, had a robust academic career, earning a Rhodes scholarship and graduating from Merton College, Oxford, in 1960 before entering the Air Force, where he rose to the rank of captain. After exiting the service, Kristofferson moved to Nashville to launch a songwriting career and at times worked as a janitor or on an oil rig. He finally broke through in 1970 with his first chart hit, Ray Price’s “For the Good Times,” which claimed #1 at Country radio and cracked the Pop Top 40.

He thereafter notched such hits as Sammi Smith’s Grammy-winning “Help Me Make It Through the Night” (1970) and the two songs with which he’d forever be most associated—“Sunday Morning Coming Down," a 1970 hit for Johnny Cash, and the Janis Joplin-popularized “Me and Bobby McGee" (1971).

While he never became a regular on the pop or rock charts as an artist, Kristofferson did score a #1 Country single in 1973 with the gospel-tinged “Why Me.” Alongside then-wife Rita Coolidge, he won Grammys for Country Vocal Performance by a Duo or Group with “From the Bottle to the Bottom” (1973) and “Lover Please” (1975).

In 1972, he launched a movie career that would last decades. His first film, Cisco Pike, was relatively obscure but brought him to the attention of Sam Peckinpah, who cast him as Billy the Kid in 1973's Pat Garrett and Billy the Kid. He avoided typecasting by appearing in the romantic comedy Alice Doesn’t Live Here Anymore and opposite Barbra Streisand in the 1976 remake of A Star Is Born, for which he won a Golden Globe.

In the '80s and '90s, Kristofferson focused on activism, speaking out against right-wing dictators around the world. He drew considerable attention when he came to Sinead O’Connor’s defense as she was booed offstage (a by-product of her having torn up a photo of Pope John Paul II on Saturday Night Live) at a 1992 benefit concert at Madison Square Garden.

Kristofferson was beloved by fellow songwriters and musicians, many of whom are paying tribute to his achievements. "The first time I saw Kris performing at the Troubadour club in L.A., I knew he was something special,” Streisand wrote on Instagram. “Barefoot and strumming his guitar, he seemed like the perfect choice for a script I was developing."

In his 2015 MusiCares speech, printed in the Los Angeles Times, Bob Dylan recalled, “Everything was very copacetic. Everything was all right until—until—Kristofferson came to town. Oh, they ain't seen anybody like him. He came into town like the wildcat that he was, flew a helicopter into Johnny Cash's backyard... not your typical songwriter. And he went for the throat... ‘Sunday Morning Coming Down.' You can look at Nashville pre-Kris and post-Kris, because he changed everything.”

That transformation was apparent on 2016's The Complete Monument & Columbia Album Collection, Sony Legacy’s 16-disc set marking Kristofferson’s 80th birthday. It includes 11 studio albums recorded from 1970 through 1981, five discs of unreleased and hard-to-find live and studio material, three concert recordings from 1970-1972 (including his 1970 Big Sur Folk Festival show) and two discs of rarities featuring non-LP singles, studio outtakes and previously unavailable demos.

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

Damon Whiteside, CEO of the Academy of Country Music, said in a statement, "Kris Kristofferson was an incredible songwriter, performer and represented the country music genre to the entire world both through his music and through his acting career. [He] was known for telling it like it is as a songwriter, and I’m so thankful we were able to honor him with the ACM Poet’s Award in 2013."

Country Music Association CEO Sarah Trahern remarked in the CMA's statement, “Theâ€¯countryâ€¯musicâ€¯worldâ€¯has lostâ€¯one of its most profoundâ€¯storytellers.â€¯I was fortunate toâ€¯getâ€¯to work withâ€¯Krisâ€¯on many projects over theâ€¯years. His charm was exactly what you’d expect—unassuming and slightly mysterious yet deeply warm. We regret that we will no longer be beneficiaries of his incredible words and talents."