He started writing songs as a little boy in Brownsville, Texas, and would go on to become one of country music’s most celebrated and prolific artists with hits including “Me and Bobby McGee” and “Help Me Make It Through the Night.” But Kris Kristofferson — who passed away on September 28 at age 88 — was also a respected actor who’d take on more than 100 roles during his decades-long career.

“The first time I saw Kris performing at the Troubadour club in L.A., I knew he was something special. Barefoot and strumming his guitar, he seemed like the perfect choice for a script I was developing, which eventually became A Star Is Born,” Barbra Streisand said of her longtime friend. The part of self-destructive singer John Howard would win Kris his first and only Golden Globe award.

Kris remained active into his 80s — performing his last concert at 84 — before announcing his retirement in 2021. The performer enjoyed spending time at his Maui, Hawaii, home with his wife of 41 years, Lisa Meyers, and their children and grandkids. “I’ve had a life of all kinds of experiences — most of them good,” said Kris, who lived by a simple rule: “Tell the truth. Sing with passion. Work with laughter. Love with heart. ’Cause that’s all that matters in the end.”