Kris Kristofferson didn’t just write songs like he was destined for country music’s Mt. Rushmore; with his windswept hair and his craggy face, the singer and songwriter also looked like a guy meant for sculpted eternity. In the mid-1970s, Kristofferson’s rugged handsomeness led to a successful sideline as an actor in Hollywood, which included a largely shirtless 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 studying literature at Pomona College and the University of Oxford — that distinguished a career that ran from the late 1960s to his death on Saturday at age 88. Here, in the order they were released, are 10 essential Kristofferson songs — his own recordings, those made by other singers and one selection that gives an idea of the lyricism he admired.
1. “Sunday Mornin’ Comin’ Down” (1970)
Johnny Cash gave Kristofferson a No. 1 country hit — and opened innumerable doors for him in Nashville — with his rendition of this searching 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 take from his self-titled debut that most vividly captures the bottom-of-the-bottle despair of a guy who “woke up Sunday morning with 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 bleak yet deeply sensual account of a one-night stand — “Take the ribbon from my hair, shake it loose and let it fall / Laying 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’s just another word for nothing left to lose,” Joplin sang in her signature blues-rock yowl — perhaps the best-known piece of wisdom in Kristofferson’s very wise catalog. “Me and Bobby McGee” topped 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 he did here, rhapsodizing in a parched croon about a woman’s redeeming devotion as producer Fred Foster ladles on just the right amount of easy-listening schmaltz.
5. “The Pilgrim, Chapter 33” (1971)
A Jackson Maine origin story.
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 cut a version of “For the Good Times” (first popularized by Ray Price) whose uncluttered groove evokes the world’s loneliest heartbeat.
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’ve been through myself on my way back to you.”
8. Willie Nelson, “Please Don’t Tell Me How the Story Ends” (1979)
It says something about the esteem in which Nelson holds his old pal’s work that he followed his blockbuster standards collection, “Stardust,” with an album of Kristofferson’s songs, including this gorgeous ballad of self-deception, which climaxes with one of the highest notes Nelson has ever sung.
9. The Highwaymen, “Highwayman” (1985)
Kristofferson reached No. 1 one more time with Jimmy Webb’s metaphysical daydream, which he recorded as a member of the Highwaymen alongside Cash, Nelson and Waylon Jennings. With Kristofferson’s death, Nelson is now the sole surviving member of that country supergroup.
10. “Sister Sinead” (2009)
Like Cash with Rick Rubin, Kristofferson teamed with producer Don Was to make a series of late-in-life LPs that didn’t just acknowledge the ravages of time but glorified them with growly, close-miked vocal performances set against intimate acoustic arrangements. In this warm and witty track from his album “Closer to the Bone,” he utilizes that grizzled perspective to redouble his support for Sinéad O’Connor, whom he famously defended after she was attacked for ripping up a photo of Pope John Paul II on “Saturday Night Live” in 1992. “It’s asking for trouble to stick out your neck / In terms of a target, a big silhouette,” Kristofferson sings, “But some candles flicker and some candles fade / And some burn as true as my sister Sinéad.”
