Kris Kristofferson, who died Sunday at the age of 88, was truly one of the greatest songwriters of the past 60 years. No less an eminence than Bob Dylan said of him, “You can look at Nashville pre-Kris and post-Kris, because he changed everything.”
And indeed he did: A Rhodes scholar who mortified his family by abandoning a promising career in the military to starve for five years before he made it as a songwriter, Kristofferson was a legendary hell-raiser who was every bit as badass as any of his contemporaries: He famously got Johnny Cash’s attention by landing a helicopter on his lawn. Yet his songs often spoke of the darker side of that lifestyle, best embodied in one of his earliest hits, “Sunday Morning, Coming Down” (see below); a later song, “From the Bottle to the Bottom,” features the timeless line: “If happiness means empty rooms and drinking in the afternoon / Then I suppose I’m happy as a clown.”
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However, as much as the gods may have overpaid him with songwriting gifts, they short-changed him in the singing department. Even on his early recordings, his voice was a deadpan alto that could barely carry many of the more-challenging melodies he’d written. Hence, some of the definitive versions of the songs listed below were performed by others, yet his delivery and skill as an actor made him the perfect singer for many others.
Kristofferson’s compositions were rarely complex — usually just a few chords, a straightforward melody and a conventional structure. Yet what he accomplished within those parameters is likely to outlive everyone reading this article. —Jem Aswad
“Me and Bobby McGee” (1970) — One of four stone-cold classics from his eponymous first album, this towering song of a love literally lost has its definitive version in the one recorded by Kristofferson’s former paramour, Janis Joplin, shortly before her death in 1970. While her exuberant version — which topped the Billboard Hot 100 in the months after her death — unquestionably highlights nuances in the song that his straightforward delivery doesn’t reach, more poignantly, she plays with the melody like a jazz singer: “From the Kennnnn-tucky coalmines to the Cal-ifornia sun, yeah Bobby shared the secrets of my soul / Through all kinds of weather, and everything that we’d done, yeah Bobby baby, kept me from the co-wo-wold.” Kristofferson would pay tribute to her in the grim “Epitaph (Black and Blue),” but the real tribute is in giving her and the world this timeless song. —Aswad
“The Pilgrim, Chapter 33” (1971) — Despite the seeming Biblical reference in its title, as Kristofferson says in a spoken introduction, this song is actually about several of his friends (including Dennis Hopper, Johnny Cash, Bobby Neuwirth, Jerry Jeff Walker and Rambling Jack Elliott). Yet it’s hard to imagine he wasn’t looking in the mirror as well, and in what may be his best vocal performance, his delivery perfectly suits the endearingly dissolute nature of the character he’s describing:
“See him wasted on the sidewalk in his jacket and his jeans
Wearin’ yesterday’s misfortunes like a smile
Once he had a future full of money, love, and dreams
Which he spent like they was goin’ outta style…”
Its verses conclude:
“But if this world keeps right on turnin’ for the better or the worse
And all he ever gets is older and around
From the rockin’ of the cradle to the rollin’ of the hearse
The goin’ up was worth the comin’ down.” —Aswad
“Sunday Morning Coming Down” (1970) — When Bob Dylan not only singles out a song for its greatness but quotes its lyrics at length (as he did in the 2015 speech referenced above), it’s hard to top. But Kristofferson’s delivery on this classic, probably the best-ever musical depiction of one hangover too many: “Well, I woke up Sunday morning with no way to hold my head that didn’t hurt/ And the beer I had for breakfast wasn’t bad so I had one more for dessert.” Kristofferson’s dry delivery perfectly embodies pain and self-loathing on the verses, but bursts open on the choruses, as if in a call for redemption. —Aswad
“Why Me” (1973) — Speaking of calls for redemption, it doesn’t get much more grim than this plea for it, a slow and mournful literal call to Jesus that apparently struck a chord with 1973 audiences, inexplicably topping the Billboard country chart and reaching No. 16 on the Hot 100. The song seemed to represent the “Sunday Morning Coming Down” character even further down a dark road: “Lord help me Jesus, I’ve wasted it/ So help me Jesus, I know what I am/ Now that I know that I’ve needed you/ So Help me Jesus, my soul’s in Your hand.” —Aswad
“Feeling Mortal” (2013) — If there was an unofficial sequel to “Why Me,” this song from 40 years later might have been it. Kristofferson was feeling his years when he penned this song about the end being in sight, 12 years or so before it came for him. But he didn’t view the end of this life as the ultimate Sunday-morning-coming-down. As anyone who knows his catalog from the 1980s forward would probably know, the sort of brilliant lyrical defeatism he specialized in in his earliest writing years wasn’t characteristic of the more sanguine attitude he took as he settled down later in life. And so, in this title track from a Don Was-produced album that was one of his last, he was more about feeling gratitude than gravity. While not without some “shaky self-esteem” at seeing an old man in the mirror in his mid-70s, and the always sobering-realization that “Here today and gone tomorrow / That’s the way it’s got to be.” And yet, he addressed God (again) rather directly for someone who didn’t specialize in spirituals, asserting that he was thankful “from here to eternity / For the artist that you are / And the man you made of me.” Most of us can only aspire to the prospect of seeing ourselves out so blissfully. —Chris Willman
“For the Good Times” (1970) — This became one of Kristofferson’s signature songs in a roundabout way; he recorded it for his debut album before Ray Price had a No. 1 country hit with it, and that was considered such a knockout that it immediately redirected attention back onto Kris as a master songwriter. (It was pure gold for everybody; Price hadn’t had a No. 1 for 11 years prior to this.) Al Green had his way with it, too. But there’s no mistaking it’s a Kristofferson composition, whomever’s singing it: No one specialized in the concept of goodbye sex better than he did. Or, you know, “bittersweetness,” if we want to put it slightly less specifically. —Willman
“Help Me Make It Through the Night” (1970) — According to legend, this deeply romantic song was inspired by an interview with Frank Sinatra in which ol’ Blue Eyes was asked what he believes in: “Booze, broads, or a bible… whatever helps me make it through the night.” Whatever the origin, it’s a remarkably suggestive song for its time and became a kind of seduction anthem, covered hundreds if not thousands of times — so much of both, in fact, that it was the backdrop for a skit when Kristofferson hosted “Saturday Night Live” in 1976 (with his then-wife Rita Coolidge as musical guest). While Kristofferson sings the song, Coolidge and Chevy Chase are seated on a bed, gazing at each other amorously. He attempts to take the ribbon from her hair, as the opening line goes, but can’t get it out and finally, by the end of the song, yanks so hard he pulls off her wig, resulting in one of Chase’s trademark slapstick tumbles. —Aswad
“Please Don’t Tell Me How the Story Ends” (1978) — For starters, this is just one of the greatest titles in pop history — right? Kristofferson almost didn’t have to write the rest of the song, it says so much in those eight words, but thank God he did. He was very much rocking the vein of the we-are-about-to-break-up-but-let’s-make-love-first songs in the early ’70s, and perhaps that’s why he didn’t cut it himself at the time, leaving it to first be recorded by Bobby Bare, before he put it on wax with then-wife Rita Coolidge on their third and final album of duets in 1978. Their story as a couple did end, soon afterward… probably less romantically than the beautiful fatalism the song itself is enveloped in. —Willman
“Here Comes That Rainbow Again” (1982) — We can make our own picks for Kristofferson’s greatest songs, but when Johnny Cash said this is not only his favorite Kristofferson song but possibly his favorite song ever, rest assured we will leave a spot for it. Is it a family or kids’ song? A gritty number rooted in a Depression-set John Steinbeck saga? All of the above? Kristofferson borrowed heavily from a chapter in “The Grapes of Wrath” to tell a simple anecdotes about strangers paying it forward in a diner. Of course he made it his own with one of the very best lines in his entire canon, following his descriptions of humble, almost cranky generosity: “Ain’t it just like a human.” That hopeful view of humanity — which obviously didn’t characterize every song in his oeuvre, but increasingly came to do so — will touch you every time you hear it… and never more so than in a moment like this. —Willman
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