Outlaw country musician and Hollywood actor Kris Kristofferson died on Saturday, September 28, at his home in Maui, Hawaii. The news was announced in a press release from Essential Broadcast Media. A cause of death was not provided, just that he was surrounded by family. Kristofferson was 88 years old.

Kristofferson was born into a military family and moved frequently, as a child, due to his father’s service. He attended Pomona College, in California, and earned a Rhodes Scholarship to the University of Oxford. While in England, he earned his master’s degree, in English literature, and attempted to enter the recording industry. He wasn’t successful with his early foray into the music industry, and he returned the United States to join the U.S. Army.

After leaving the Army, in 1965, Kristofferson moved to Nashville to try again to make it in the music business. While working as a janitor at Columbia Records, he started to make a name for himself as a songwriter. Hits like “Me and Bobby McGee” and “Sunday Morning Coming Down” were recorded by Janis Joplin and Johnny Cash. Waylon Jennings, Ray Price, and Gladys Knight also recorded Kristofferson’s songs.

Kristofferson released his first studio album, Kristofferson, in 1970, and he continued to gain recognition with 1971’s The Silver Tongued Devil and I. The next year, 1972, Kristofferson had a great showing at the Grammy Awards, as he received three nominations for Best Country Song. Ultimately, “Help Me Make It Through the Night” prevailed over “Me and Bobby McGee” and “For the Good Times.” Kristofferson was also nominated twice for Song of the Year.

While Kristofferson continued to release albums at a regular clip, he also became a familiar face on the silver screen. In the 1970s, he acted in Cisco Pike, Pat Garrett and Billy the Kid, and more, but he really turned heads as Barbra Streisand’s co-star in the 1976 version of A Star Is Born, earning a Golden Globe Award for his performance. Kristofferson continued to act into the 2010s, appearing in Heaven’s Gate, several Blade films, Tim Burton’s 2001 Planet of the Apes, and many other productions.

Another of Kristofferson’s major musical achievements began in 1985 when he formed the Highwaymen with fellow outlaw country music superstars Johnny Cash, Waylon Jennings, and Willie Nelson. Across their decade-long run, they released three studio albums— 1985’s Highwayman, 1990’s Highwayman 2, and 1995’s The Road Goes on Forever—played countless shows, and starred together in Stagecoach.