The Essential Kris Kristofferson

In Issue 1076, Ethan Hawke profiles Kris Kristofferson, the last outlaw poet. The singer's epic journey has taken him from Oxford to the Army Rangers to Nashville and Hollywood. Here's a guide to 20 of the best tracks he's written along the way.

"Sunday Morning Coming Down" (1970)
The greatest song about a hangover ever written. Johnny Cash's 1970 recording launched Kristofferson's career.
Listen to Johnny Cash's version
Listen to Kris Kristofferson's version

"Best of All Possible Worlds" (1970)
Kris' humor shines in this ode to wine and lonely girls, but it's the jailer who tells the truth: "If booze was just a dime a bottle, boy, you couldn't even buy the smell."
Listen to Kris Kristofferson's version

"Help Me Make It Through the Night" (1970)
Now a country standard, this plea for lovin' was too racy for Nashville in the Seventies. Gladys Knight best captured the song's tenderness in her 1972 cover.
Listen to Gladys Knight's version
Listen to Kris Kristofferson's version

"Me and Bobby McGee" (1970)
Somehow Kris managed to unite the hippie ideals with his shitkicking Texas spirit. Janis Joplin's version, from 1971's Pearl, was her only Number One song.
Listen to Janis Joplin's version
Listen to Kris Kristofferson's version

"For the Good Times" (1970)
A dark waltz of doomed love. "He can slay you with a simple sentiment of longing," says Norah Jones, who covered the tune with the Little Willies.
Listen to Kris Kristofferson's version

"Loving Her Was Easier (Than Anything I'll Ever Do Again)" (1971)
Willie Nelson has called this his favorite Kristofferson song, which he covered on his 1979 album Willie Nelson Sings Kristofferson.
Listen to Willie Nelson's version
Listen to Kris Kristofferson's version

"The Pilgrim – Chapter 33" (1971)
Written about Kristofferson's hard-living heroes (Cash, Dennis Hopper, Ramblin' Jack), this song ended up as a self-portrait: "He's a walking contradiction, partly truth and partly fiction." Brilliantly covered by Emmylou Harris on The Pilgrim: A Celebration of Kris Kristofferson (2006).
Listen to Kris Kristofferson's version

"Silver Tongued Devil" (1971)
Written when Waylon Jennings and Kris were touring and stirring up trouble with the ladies, but it's Waylon's son Shooter who sings it best.
Listen to Kris Kristofferson's version

"When I Loved Her" (1971)
Kris can get away with the simple sentiment of the lyrics ("She seemed to be so proud of me just walking holding hands, and she didn't think that money was the measure of a man") because he shoots straight from the gut on this cut from The Silver Tongued Devil and I, also recorded by Ray Price.
Listen to Kris Kristofferson's version

"Why Me" (1973)
Kristofferson's biggest hit as a solo recording artist, featuring backing vocals from his future wife, Rita Coolidge, and Larry Gatlin. It doesn't matter what Gospel Choir shakes the steeple with Kris' song, they can never capture the pain that Kris delivers in his hungover prayer of gratitude.
Listen to Kris Kristofferson's version