Kris Kristofferson, the legendary actor and country singer-songwriter, has passed away at the age of 88. A representative confirmed that he died peacefully surrounded by family at his home in Maui on Saturday, September 28.

In a heartfelt statement shared with PEOPLE, Kristofferson’s family expressed their sorrow, saying, “It is with a heavy heart that we share the news our husband/father/grandfather, Kris Kristofferson, passed away peacefully on Saturday, September 28 at home. 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.”

Born on June 22, 1936, in Brownsville, Texas, Kristofferson was the son of Mary Ann (née Ashbrook) and Lars Henry Kristofferson, a Swedish immigrant and U.S. Army officer. His passion for country music began early; he famously wrote his first song, “I Hate Your Ugly Face,” at just 11 years old. Kristofferson’s childhood was marked by frequent moves due to his father’s military career, settling in San Mateo, California, during his teenage years.

Kristofferson showcased his literary talents at an early age, with two short stories published in Atlantic Monthly when he was just 18. He attended Pomona College, excelling in sports and academics, which led to his feature in Sports Illustrated’s “Faces in the Crowd” in 1958. After earning a bachelor’s degree in creative writing, he received a Rhodes Scholarship to study at Oxford University, where he obtained a master’s in English literature.

Following his education, Kristofferson joined the U.S. Army and became a helicopter pilot. While stationed in West Germany, he formed a band with fellow soldiers and began writing songs. His time in Nashville, inspired by the vibrant music community, prompted him to leave the Army in 1965 to pursue music full-time. He later recalled his love for the supportive atmosphere in Nashville and the connection between established and emerging artists.

Kristofferson’s songwriting career took off in Nashville, where he penned classics like “For the Good Times” and “Sunday Mornin’ Comin’ Down.” His songs were recorded by numerous artists, including Ray Price and Johnny Cash, earning him critical acclaim and a loyal fan base. In 1971, his collaboration with Janis Joplin, “Me and Bobby McGee,” became a massive hit, further solidifying his place in music history.

In addition to his music career, Kristofferson made a name for himself in Hollywood, starring in films such as Cisco Pike, Pat Garrett & Billy the Kid, and Alice Doesn’t Live Here Anymore. His most notable role came in 1976 when he portrayed the troubled rock star John Norman Howard in the remake of A Star Is Born, earning a Golden Globe for Best Actor in 1977. He also gained recognition for his portrayal of Whistler in the Blade trilogy.

Kristofferson was part of the country supergroup The Highwaymen, alongside Johnny Cash, Waylon Jennings, and Willie Nelson. Their self-titled album topped the charts in 1985, followed by two more successful albums.

Over his illustrious career, Kristofferson garnered numerous awards, including three Grammy Awards and a Lifetime Achievement Award from the Recording Academy in 2014. He was inducted into the Country Music Hall of Fame in 2004 and received an Oscar nomination for Best Original Song in 1985 for his work in Songwriter.

In 2013, Kristofferson bravely shared his struggles with memory loss, initially misdiagnosed as Alzheimer’s disease, later found to be Lyme disease. With treatment, he experienced significant improvement.

Kristofferson officially announced his retirement from music in 2021, having released his final studio album, The Cedar Creek Sessions, in 2016. He is survived by his wife, Lisa, eight children, and seven grandchildren. His legacy as a remarkable artist and storyteller will continue to inspire generations.