Kris Kristofferson Photography

When Kris Kristofferson left the army in 1965, he went straight to Nashville to become a singer/songwriter and, along the way, added acting to his resume. Though it took a few years for either of his careers to get off the ground, the floodgates of success flew wide open once he debuted with a self-titled album on Monument Records in 1970.

On the artist side of the coin, he’s perhaps best known for the smashes “Me and Bobby McGee,” “Help Me Make It Through the Night,” “For the Good Times,” and “Sunday Mornin’ Comin’ Down.” When it comes to movies, his starring roles include Alice Doesn’t Live Here Anymore and the Golden Globe-winning A Star Is Born opposite Barbara Streisand.

Kristofferson is also known for frequent collaborations with former wife/fellow country star Rita Coolidge, plus his time in the famed supergroup the Highwaymen (alongside Johnny Cash, Willie Nelson, and Waylon Jennings). In 2004, this troubadour was inducted into the Country Music Hall of Fame and he’s still as active as ever even as he nears his eighth decade.