Kris Kristofferson’s 10 Best Songs

Kris Kristofferson, who died Saturday at age 88, was truly one of the greatest songwriters of the last 60 years. None other than Bob Dylan said of him: “You can look at Nashville before and after Kris, because he changed everything.”

And he did: Kristofferson, a Rhodes scholar who humiliated his family by giving up a promising military career and starving for five years before making it as a songwriter, was a legendary hell-raiser who was as badass as any Others of his contemporaries: He famously caught Johnny Cash’s attention by landing a helicopter on his lawn. Yet his songs often spoke to the darker side of this lifestyle, best expressed in one of his earliest hits: “Sunday Morning, Coming Down” (see below); a later song, “From the Bottle to the Bottom,” contains the timeless line: “If happiness means empty rooms and afternoon drinking / Then I guess I’m happy as a clown.”

But as much as the gods may have overpaid him with his songwriting talents, they left him short in the singing department. Even on his early recordings, his voice was an expressionless contralto that could barely handle many of the more sophisticated melodies he had written. Therefore, some of the final versions of the songs listed below were performed by others, but his performance and skill as an actor made him the perfect singer for many others.

Kristofferson’s compositions were rarely complex – they usually consisted of just a few chords, a straightforward melody and a conventional structure. But what he accomplished within those parameters will likely outlive anyone reading this article. —Jem Aswad

“Me and Bobby McGee” (1970) – One of four stone-cold classics from his eponymous first album, this powerful song of love literally lost has its definitive version in the version recorded by Kristofferson’s former lover Janis Joplin shortly before her death in 1970. While her exuberant version – which reached the top of the Billboard Hot 100 in the months after her death – undoubtedly highlights nuances in the song that his straightforward delivery doesn’t, and even more poignantly, she plays with the melody like a jazz singer: “From the Kennnnn-Tucky coal mines for Cal-ifornia sun, yes, Bobby shared the secrets of my soul / In all the weather and in all that we had done, yes Bobby baby, stopped me from doing it co-where-wold.” Kristofferson would pay tribute to her with the somber “Epitaph (Black and Blue),” but the true tribute is giving her and the world this timeless song. —Aswad

“The Pilgrim, Chapter 33” (1971) – Despite the seemingly biblical reference in the 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). Still, it’s hard to imagine that he hasn’t looked in the mirror, and in perhaps his best vocal performance, his delivery perfectly matches the lovable, debauched nature of the character he describes:

“See him lying exhausted on the sidewalk in his jacket and jeans
I carry yesterday’s misfortune like a smile
He once had a future full of money, love and dreams
What he spent like they were going out of fashion…”

His verses conclude:

“But if this world continues to turn, for better or for worse
And all he ever becomes is older and older
From the rocking of the cradle to the rolling of the hearse
The climb was worth it.” —Aswad

“Sunday Morning Coming Down” (1970) – When Bob Dylan not only singles out a song for its greatness, but also quotes its lyrics at length (as he did in the aforementioned 2015 speech), it’s hard to beat it. But Kristofferson’s delivery on this classic, probably the best musical depiction of one too many hangovers ever: “Well I woke up Sunday morning with no way to hold my head that didn’t hurt/And the beer I had for breakfast.” “It wasn’t bad, so I had another for dessert.” Kristofferson’s dry delivery perfectly embodies pain and self-loathing in the verses, but erupts in the choruses as if calling for redemption. —Aswad

“Why Me” (1973) – When we talk about calls for salvation, it doesn’t get much darker than this plea, a slow and sad, literal call to Jesus that apparently resonated with audiences in 1973, inexplicably topping the Billboard country charts and charted at No. 16 on the Hot 100. The song seemed to portray the “Sunday Morning Coming Down” character even further down a dark path: “Lord, help me Jesus, I’ve wasted it/So help me, Jesus, I know what I am/Now that I know.” that I needed you/So help me, Jesus, my soul is in your hand.” —Aswad

“Feeling Mortal” (2013) — If there was an unofficial sequel to “Why Me,” it might have been this song from 40 years later. Kristofferson felt his years when he wrote this song about the end being in sight, about 12 years before it came for him. But he didn’t view the end of that life as the ultimate Sunday morning descent. As anyone who has known his catalog since the 1980s would probably know, the kind of brilliant lyrical defeatism in which he specialized in his early years as a writer was not characteristic of the more confident attitude he adopted later on settled down in life. And so this title track of a Don Was-produced album, one of his last, was more about gratitude than gravity. However, not without a certain “shaky self-esteem” when you see an old man in his mid-70s in the mirror, and the always sobering realization: “Here today and gone tomorrow / That’s how it has to be.” And yet he turned around quite a bit (again). directly to God for someone who didn’t specialize in spirituals, claiming he was grateful “from here to eternity / For the artist you are / And the man you made me.” Most of us can only long for the prospect of such a happy life. —Chris Willman

“For the Good Times” (1970) — This became, in a roundabout way, one of Kristofferson’s signature songs; He recorded it for his debut album before Ray Price scored a No. 1 country hit with it, and it was considered so stunning that it immediately brought attention back to Kris as a master songwriter. (It was pure gold for everyone; Price hadn’t had a No. 1 in 11 years.) Al Green also had his way. But there is no doubt that it is a Kristofferson composition, no matter who sings it: no one has specialized in the concept Goodbye sex better than him. Or, you know, “bittersweetness,” if we want to put it light less concrete. —Willman

“Help Me Get Through the Night” (1970) – Legend has it that this deeply romantic song was inspired by an interview with Frank Sinatra, in which old Blue Eyes was asked what he believed in: “Alcohol, women or a Bible…whatever helps me get through the night.” What Whatever the origin, it’s a remarkably suggestive song for its time and became something of a seduction anthem, covered hundreds if not thousands of times – so much of both, in fact, that it formed the backdrop for a skit as Kristofferson “Saturday Night Live” in 1976 (with his then-wife Rita Coolidge as musical guest). As Kristofferson sings the song, Coolidge and Chevy Chase sit on a bed and look at each other in love. He tries to pull the ribbon out of her hair, as the opening line says, but can’t get it out and ends up ripping it so hard at the end of the song that he rips off her wig, resulting in one of Chase’s trademark slapstick scenes. leads to falls. —Aswad

“Please Don’t Tell Me How the Story Ends” (1978) — First of all, this is simply one of the greatest tracks in pop history – right? Kristofferson almost didn’t have to write the rest of the song, those eight words say so much, but thank God he did. In the early ’70s he rocked in the style of we-are-about-to-break-up-but-let-make-love-first songs, and maybe that’s why he didn’t make it himself back then has time and first had it recorded by Bobby Bare before he put it on wax with his then wife Rita Coolidge in 1978 on their third and final duet album. Their story as a couple ended soon after…probably less romantic than the beautiful fatalism that shrouds the song itself. —Willman

“Here Comes That Rainbow Again” (1982) — We can make our own picks for Kristofferson’s best songs, but when Johnny Cash said this was not only his favorite Kristofferson song, but possibly his favorite song ever, rest assured we’ll leave a spot for it. Is it a family or children’s song? A dark number rooted in a John Steinbeck saga from the Depression? All of the above? Kristofferson made heavy use of a chapter in The Grapes of Wrath to tell a simple anecdote about strangers paying money at 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, of course, isn’t in every song in his oeuvre, but increasingly came into it – will touch you every time you hear it… and never more than in a moment like this. —Willman