Supremely gifted songwriter, singer and actor Kris Kristofferson died Saturday (Sept. 28) at his home in Maui, Hawaii, at age 88.

Born Kristoffer Kristofferson in Brownsville, Texas in June 1936; he family soon moved to California. Kristofferson’s short stories were published in The Atlantic Monthly and soon after, he became a Rhodes Scholar who studied in Oxford. His life also included time as a Golden Gloves boxer, and an Army ranger who also flew helicopters (and famously once landed a helicopter on Johnny Cash’s lawn in order to get Cash to listen to a demo tape), an A-list actor, a writer and a creator equally inspired by the works of William Blake as songcrafters such as Bob Dylan. In the Army, Kristofferson rose to the rank of captain, but when he was commissioned to teach English at West Point, he abandoned that opportunity in order to head to Nashville to pursue songwriting.

He began working as a janitor at Nashville’s Columbia Studios, which allowed him to listen in on sessions including Dylan’s 1966 Blonde on Blonde album. His nuanced, elegant lyricism style led to Kristofferson earning multiple No. 1s as a writer of songs made famous by other artists, including Ray Price, Johnny Cash, Roger Miller and Sammi Smith. In 1970, he issued his eponymous first album, Kristofferson, which included his own versions of the hits “Me and Bobby McGee,” “Help Me Make It Through The Night” and “Sunday Mornin’ Comin’ Down,” all of which he originally penned.

He also earned his own No. 1 country hit with “Why Me,” and another as part of the country supergroup The Highwaymen, with Johnny Cash, Waylon Jennings and Willie Nelson.

As an actor, he starred in films and television series including Alice Doesn’t Live Here Anymore, A Star Is Born (in a Golden Globe-nominated performance opposite Barbra Streisand), Blade (opposite Wesley Snipes), Pat Garrett and Billy the Kid, Stagecoach, Convoy, Songwriter and Fire Down Below.

Kristofferson was inducted into the Country Music Hall of Fame in 2004 — and a decade later, earned the Grammy Lifetime Achievement Award.

Below, we look at 11 songs or albums that Kristofferson had a hand in as an artist or songwriter that reached No. 1 on various Billboard charts.