Kris Kristofferson: 12 Essential Songs

Kris Kristofferson, who was 88 when he died on Saturday, embedded enduring aphorisms into his songs. “Freedom’s just another word for nothing left to lose,” he observed in “Me and Bobby McGee.” In “Help Me Make It Through the Night,” he wrote, “Yesterday is dead and gone/And tomorrow’s out of sight.” And in “For the Good Times,” he urged, “There is no need to watch the bridges that we’re burning.”

Those are stoic lines, delivered matter-of-factly, often tucked into tales about facing up to some kind of loss: of a lover, a friend, a hope, a chance, fleeting time. Kristofferson’s characters are often isolated, luckless, drunk or high, but they’re still seeking redemption or at least trying to move on — like Casey, in “Casey’s Last Ride,” who was “seeing his reflection in the lives of all the lonely men/who reach for anything they can to keep from going home.”

Kristofferson established himself as a songwriter as the 1970s began, and his early songs were his most lasting ones. His willingness to sing unpretty stories and his homey melodies were foundations for the outlaw country movement of the 1970s. Bob Dylan has said, “You can look at Nashville pre-Kris and post-Kris, because he changed everything.”

After a detour through 1970s movie stardom, Kristofferson shared the outlaw movement’s victory lap, in the 1980s, when he joined Johnny Cash, Willie Nelson and Waylon Jennings in the Highwaymen. He went on to write politically charged songs and the homilies of an elder. His voice was serviceable but not striking in his early years, and it grew much gruffer through the decades. But it was always forthright enough to put across the unvarnished substance of his music.

Here, in chronological order, are 12 of Kristofferson’s essential songs. Listen on Spotify and Apple Music.

‘Me and Bobby McGee’ (1970)

Kristofferson’s own version of this tale of hitchhiking, harmonica-playing lovers, from his debut album, is far more wistful and less cathartic than Janis Joplin’s No. 1 hit version, released in 1971 after her death. Where she turned its outro of “la-da-das” into an ecstatic rave-up, Kristofferson lets them trail off, like a memory receding into the distance.