Kris Kristofferson: “Me and Bobby McGee” and 9 other important songs

Kris Kristofferson hasn’t just written songs like he’s destined for country music’s Mt. Rushmore; With his windswept hair and rugged face, the singer-songwriter also looked like a guy destined for eternity. In the mid-1970s, Kristofferson’s rugged beauty led to a successful sideline as an actor in Hollywood, which included a largely nude role opposite Barbra Streisand in her rock ‘n’ roll remake of “A Star Is Born.” But it was the depth and invention of Kristofferson’s writing – a talent he honed while studying literature at Pomona College and Oxford University – that distinguished a career that spanned from the late 1960s until his death on Saturday at the age of 11 88 years was enough. Here, in the order they were released, are 10 essential Kristofferson songs – his own recordings, those by other singers, and a selection that gives a sense of the lyricism he admired.

1. “Sunday Mornin’ Comin’ Down” (1970)

Johnny Cash gave Kristofferson a No. 1 country hit – and opened countless doors for him in Nashville – with his rendition of this piercing drunkard’s lament, which Cash recorded live at Nashville’s Ryman Auditorium during a taping of his popular ABC variety show . But it’s Kristofferson’s own version of his self-titled debut that most clearly captures the deepest despair of a man who “woke up on Sunday morning and had no way to hold my head that didn’t hurt.”

2. Sammi Smith, “Help Me Make It Through the Night” (1970)

Another No. 1 on Billboard’s country singles chart, this dark but deeply sensual account of a one-night stand – “Take the ribbon from my hair, shake it loose and let it fall / Lay soft against your skin, like the shadows on the “wall” (!) – won the Grammy Award for Country Song of the Year at a ceremony where Kristofferson was nominated in that category for three different tunes.

3. Janis Joplin, “Me and Bobby McGee” (1971)

“Freedom is just another word for nothing left to lose,” sang Joplin in her signature blues-rock twang—perhaps the best-known piece of wisdom in Kristofferson’s very clever catalog. “Me and Bobby McGee” reached the top of the Hot 100 in March 1971, less than six months after Joplin’s death at age 27.

4. “Loving her was easier (than anything I’ll ever do again)” (1971)

Kristofferson never sounded more like Leonard Cohen than here, raving about a woman’s redemptive devotion in parched vocals while producer Fred Foster added just the right amount of easy-listening schmaltz.

5. “The Pilgrim, Chapter 33” (1971)

An origin story from Jackson Maine.

6. Al Green, “For the Good Times” (1972)

A year after Gladys Knight showed what a soul singer could do with Kristofferson’s material in her 1971 recording of “Help Me Make It,” Green recorded a version of “For the Good Times” (first popularized by Ray Price) whose tidy groove is reminiscent of the loneliest heartbeat in the world.

7. “Why Me” (1972)

Kristofferson’s only chart-topper as a solo artist finds him on his knees, begging God to use him as a vessel: “Maybe, Lord, I can show someone else what I went through on the way back to you.”

8. Willie Nelson, “Please Don’t Tell Me How the Story Ends” (1979)

It says something about the appreciation Nelson has for his old pal’s work that he followed up his blockbuster standard collection Stardust with an album of Kristofferson’s songs, including this beautiful ballad of self-deception that climaxes on one of the highest notes Nelson has ever sung.

9. The Highwaymen, “Highwayman” (1985)

Kristofferson reached No. 1 again with Jimmy Webb’s Metaphysical Daydream, which he recorded as a member of the Highwaymen alongside Cash, Nelson and Waylon Jennings. Following Kristofferson’s death, Nelson is now the only surviving member of this country’s supergroup.

10. “Sister Sinead” (2009)

Like Cash with Rick Rubin, Kristofferson teamed up with producer Don Was to make a series of late-period LPs that not only acknowledged the ravages of time, but also glorified them with growling, up-close vocal performances set against intimate acoustic arrangements. In this warm and witty track from his album Closer to the Bone, he uses this dark perspective to double down on his support for Sinéad O’Connor, whom he famously defended after she was attacked for posting a photo of Pope John Paul II. had torn “Saturday Night Live” in 1992. “It takes effort to stick your neck out / In relation to a target, a big silhouette,” Kristofferson sings, “But some candles flicker and some candles fade / And some burn like that.” true as mine.” Sister Sinéad.”