Kris Kristofferson Through the Years: Look Back at His Life in Photos

Born on June 22, 1936, singer-songwriter-actor Kris Kristofferson is still a legendary outlaw-country influencer despite being retired. Not only did the Grammy winner write classic songs for himself, he is credited for writing hits such as "Me and Bobby McGee" and "For the Good Times" for other artists. Kristofferson won a Golden Globe for his performance opposite Barbra Streisand in 1976's A Star Is Born and acted in many other films, most notably Pat Garrett & Billy the Kid, Blume in Love, Alice Doesn't Live Here Anymore, Lone Star, Stagecoach and the Blade trilogy. In celebration of the Country Music Hall of Famer's 86th birthday, take a look back with us at his life in images.

1967: Kristofferson Signs to Epic Records

Kris Kristofferson was born in Brownsville, Texas on June 22, 1936 in the middle of the Great Depression. Under pressure from his family, a young Kristofferson joined the U.S. Army and became a helicopter pilot but left after several years to pursue a songwriting career. He moved to Nashville and got a job sweeping floors at Columbia Recording Studios, where he ran into June Carter and asked her to give his demo tape to Johnny Cash. Weeks later, Kristofferson landed a helicopter in Cash's yard to get his attention, which somehow worked out well. Kristofferson signed with Epic Records in 1967 and released his first single, "Golden Idol." The song was not a hit, but Kristofferson was beginning to get the country world's attention.

1970s: Kristofferson Establishes Himself As Country Artist and Actor

The 1970s are when everything started coming together professionally for Kris Kristofferson. Janis Joplin, who had dated Kristofferson, scored a huge hit with "Me and Bobby McGee," which he wrote. Then, in 1971, Kristofferson's song "Lovin' Her Was Easier (Than Anything I'll Ever Do Again)" established him as a singer. He won the Grammy for Best Country Song for that same year's "Help Me Make It Through the Night." In addition to hit albums, Kristofferson's acting career also started taking off. He starred in three movies directed by Sam Peckinpah and won a Golden Globe for his performance in 1976's A Star Is Born opposite Barbra Streisand.

1985: Kristofferson Joins the Highwaymen

Willie Nelson and Kris Kristofferson are friends who worked together on the soundtrack album Music from Songwriter, so they continued their partnership and added Johnny Cash and Waylon Jennings to the mix to form the supergroup the Highwaymen. Their first album, 1985's Highwayman, was a huge success, and the four continued to work together for many years.

1998: Kristofferson Makes His First Appearance As Abraham Whistler in Blade

Kristofferson's acting career continued to flourish in the 1990s. He appeared in John Sayles' Lone Star, which was nominated for a Best Screenplay Oscar. In 1998, Kris Kristofferson made his first appearance as Abraham Whistler in the action-horror movie Blade. In the film, Whistler is the mentor to the titular superhero, played by Wesley Snipes, with vampire strengths and none of their weaknesses. Kristofferson reprised the fan-favorite role in two more sequels.

2004: Kristofferson Is Inducted into the Country Music Hall of Fame

In the aughts, Kristofferson was showered with many awards and honors for a lifetime of music, songwriting and acting. In 2003, he received a "Spirit of Americana" award from the Americana Music Association. One year later, he was inducted into the Country Music Hall of Fame. In 2006, he was honored with the Johnny Mercer Award from the Songwriters Hall of Fame, the same year he released his first album of new material, The Old Road, in 11 years. In 2007, CMT bestowed Kristofferson with the Johnny Cash Visionary Award. Kristofferson said of winning the latter, "John was my hero before he was my friend, and anything with his name on it is really an honor in my eyes."

2016: Kristofferson Releases His Final Album

Kristofferson released his final album, The Cedar Creek Sessions, in 2016. The album was nominated for a Best Americana Album Grammy. He is pictured here performing at Golden Gate Park in San Francisco in 2016. In 2019, he reunited with former costar Barbra Streisand for an exclusive performance in London's Hyde Park.

2021: Kristofferson Announces His Retirement

Kristofferson's last full concert performance was at the Sunrise Theatre in Fort Pierce, Florida on February 5, 2020. In 2021, in the middle of the COVID-19 pandemic, it was announced that Kristofferson had retired. He married his third wife, Lisa Meyers, in 1983 and has a total of eight children from all of his marriages. Happy birthday to Kristofferson, a living legend, who reportedly said that he wants the first three lines of Leonard Cohen's "Bird on the Wire" on his tombstone: "Like a bird on the wire/Like a drunk in a midnight choir/I have tried in my way to be free."

READ MORE: Flashback: Barbra Streisand & Kris Kristofferson Perform a Steamy Duet in 1976 Romance 'A Star is Born'