Outlaw country icon and Hollywood star Kris Kristofferson passed away on September 28 at his Maui, Hawaii residence. The announcement came via a press release from Essential Broadcast Media. The cause of his death has not been disclosed, though it’s noted he was with family at the time. He was 88 years old.
Kristofferson grew up in a military household, resulting in a childhood marked by frequent relocations due to his father’s career. He began his academic journey at Pomona College in California and later earned a Rhodes Scholarship to attend the University of Oxford. During his time in England, he pursued a master’s degree in English literature while attempting to launch a music career. However, his early efforts were not fruitful, leading him to return to the U.S. and enlist in the Army.
Upon leaving military service in 1965, Kristofferson made his way to Nashville to give the music business another shot. He worked as a janitor at Columbia Records while slowly rising through the ranks as a songwriter. His talent led to iconic tracks such as “Me and Bobby McGee” and “Sunday Morning Coming Down,” performed by artists like Janis Joplin and Johnny Cash. His songwriting prowess attracted attention from other legends, including Waylon Jennings, Ray Price, and Gladys Knight.
In 1970, Kristofferson released his debut album, simply titled Kristofferson, followed by The Silver Tongued Devil and I in 1971. The following year, he made a splash at the Grammy Awards, receiving three nominations for Best Country Song, ultimately winning for “Help Me Make It Through the Night,” which triumphed over his own “Me and Bobby McGee” and “For the Good Times.” He also earned two nominations for Song of the Year during this period.
While Kristofferson consistently produced music, he also ventured into acting during the 1970s. He appeared in films such as Cisco Pike and Pat Garrett and Billy the Kid, but it was his role alongside Barbra Streisand in the 1976 remake of A Star Is Born that truly captured attention, earning him a Golden Globe Award. His acting career continued into the 2010s, with appearances in Heaven’s Gate, several Blade films, Tim Burton’s 2001 adaptation of Planet of the Apes, and more.
In another significant chapter of his musical journey, Kristofferson co-founded the Highwaymen in 1985, joining forces with fellow country legends Johnny Cash, Waylon Jennings, and Willie Nelson. Over their decade-long collaboration, they released three studio albums—1985’s Highwayman, 1990’s Highwayman 2, and 1995’s The Road Goes on Forever—and played numerous shows, even appearing together in the film Stagecoach.