Kris Kristofferson has died at the age of 88.

The Country Music Hall of Fame singer-songwriter and Golden Globe-winning actor passed away “peacefully in his home in Maui, Hawaii on Saturday, September 28th, surrounded by family,” according to a spokesperson.

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

Kristofferson was best known for songs such as “Me and Bobby McGee”, his work in the supergroup The Highwaymen alongside Johnny Cash, Waylon Jennings, and Willie Nelson, and his starring roles in films like A Star Is Born, Blade, and Heaven’s Gate.

Hailing from the border town of Brownsville, Texas, Kristofferson was a true multi-dimensional talent. Prior to moving to Nashville to pursue songwriting, he was a star football player and Golden Gloves boxer, who graduated with a Bachelor of Arts degree, summa cum laude, in literature from Pomona University and received a Rhodes Scholarship to the University of Oxford. Following his studies, he joined the military, where he flew helicopters as an Army Ranger.

Upon his move to Nashville, Kristofferson initially found success as a songwriter for others, striking hits on behalf of Johnny Cash, (“Sunday Mornin’ Comin’ Down”), Ray Price (“For the Good Times”), Jerry Lee Lewis (“Once More with Feeling”), and Waylon Jennings (“The Taker”).

Kristofferson released his self-titled debut album in 1970 to minimal success. However, after his former girlfriend, Janis Joplin, posthumously achieved a number one single with his song “Me and Bobby McGee” on her album Pearl the following year, Kristofferson rebranded and reissued his album under the title Me and Bobby McGee, propelling it to No. 10 on the Billboard country charts. The album track “Help Me Make It Through the Night” went on to win Kristofferson his first Grammy for Best Country Song.

Kristofferson’s sophomore album, 1971’s The Silver Tongued Devil and I, performed even better commercially, achieving gold record status on the back of the hit single “Lovin’ Her Was Easier (Than Anything I’ll Ever Do Again).”

Starting in the 1970s, Kristofferson began to focus more of his attention on acting, taking on roles in films including Martin Scorsese’s Alice Doesn’t Live Here Anymore, the road action comedy Convoy, and the sports comedy Semi-Tough. His definitive performance came in 1976 when he started opposite Barbra Streisand in A Star is Born, a role which earned him the Golden Globe Award for Best Actor.

In 1980, Kristofferson starred in Michael Cimino’s infamous post-Deer Hunter disaster, Heaven’s Gate. After the film bombed at the box office, he refocused his attention on music, teaming up with Willie Nelson, Dolly Parton, and Brenda Lee on The Winning Hand, a collaborative album which saw the artists revisit songs they had originally made for the Monument label during the mid-1960s. Kristofferson and Nelson then continued their partnership by enlisting Johnny Cash and Waylon Jennings to form a supergroup called The Highwaymen. The quartet released a trio of albums between 1985 and 1995

Kristofferson continued to take on acting roles throughout the 1980s and ’90s, including as the vampire hunter Abraham Whistler in the Blade trilogy, plus in Tim Burton’s remake of Planet of the Apes, He’s Just Not That Into You, and Dolphin Tale. He and Nelson also starred together in the 1984 satirical comedy Songwriter, with the film’s score earning Kristofferson an Academy Award nomination.

Over the course of his career, Kristofferson was nominated for 13 Grammy Awards, winning three. He was inducted into the Songwriters Hall of Fame in 1985, the Country Music Hall of Fame in 2004, and in 2014, he received a Grammy Lifetime Achievement Award.