Ethan Hawke Picks 20 Key Kris Kristofferson Tracks

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.

“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.”

“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.

“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.

“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.

“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.

“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).

“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.

“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.

“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.

“Broken Freedom Song” (1974)
The raw emotion of this track, part of an album of songs written about alcohol and drug abuse, just slays the listener.

“I’ve Got to Have You” (1974)
This love song was most popularly covered by Carly Simon on her album Anticipation, but people don’t talk about Sammi Smith’s cover (which peaked at Number 13 on the country charts) as much — and the woman has soul.

“Please Don’t Tell Me How the Story Ends” (1979)
Ronnie Milsap scored a Number One single with this wistful plea, but the recording straight from the horse’s mouth (off his third and final duet album with former wife Rita Coolidge) is the one to hear.

“Maybe You Heard” (1981)
For anyone who has gone through a divorce, this song is not mysterious in the slightest. Todd Snider — one of Kris’ favorites from the new generation — gave his gospel interpretation on The Pilgrim: A Celebration of Kris Kristofferson.

“Here Comes That Rainbow Again” (1983)
Johnny Cash said this track, a retelling of a scene from The Grapes of Wrath, “might be my favorite song by any writer.” Appears on the Highwaymen’s 1995 album The Road Goes On Forever.

“They Killed Him” (1986)
A lament for Gandhi, King and Christ, covered by Dylan on Knocked Out Loaded. “Havin’ Dylan cover one of your songs is like being a playwright and having Shakespeare act in your play,” Kris says.

“Sandinista” (1990)
This song was written to declare support for Nicaraguan rebels of the same name, and it’s a great example of Kris’ more political work. Patty Griffin recorded a beautiful version for a 2006 tribute record.

“A Moment of Forever” (1995)
One of Kris’ best love songs, memorably covered by Willie Nelson. “I started singing it to him,” Kristofferson remembers, “and all of a sudden Willie started giggling. He thought I was singing the words about him! I was so embarrassed. Later Willie cut the damn thing and titled his album after it.”

“The Circle” (2003)
Kris’ intro to the song on Broken Freedom Song: Live from San Francisco is equally as insightful as the song, which was inspired by the stories of the disappeared ones (Los Olivados) in Argentina and the death of an Iraqi artist during the Clinton administration’s bombing of Baghdad.

“Pilgrim’s Progress” (2006)
Kris has always been political, and this cut — which has been called a sequel to 1971’s “The Pilgrim – Chapter 33” — proves the old dog has still got it. Kris says it’s a track that “tells the truth, a progress report.”

[From Issue 1076 — April 16, 2009]