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

And indeed he did: Kristofferson, a Rhodes scholar who humiliated his family by giving up a promising career in the military to starve for five years before making it as a songwriter, was a legendary hell-raiser who was just as badass like all his colleagues. contemporaries: He caught the attention of Johnny Cash by landing a helicopter on his lawn. Yet his songs often spoke to the dark side of that lifestyle, best embodied in one of his first 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 think I’m as happy as a clown.”

But as much as the gods have overpaid him with songwriting gifts, they have shortchanged him in the singing department. Even on his early recordings, his voice was a deadpan contralto that could barely carry many of the more challenging melodies he had written. Therefore, some of the final versions of the songs mentioned below were performed by others, but his delivery and skill as an actor made him the perfect singer for many others.

Kristofferson’s compositions were rarely complex: usually only a few chords, a clear melody and a conventional structure. But what he accomplished within these parameters will likely outlast anyone reading this article. —Jem Aswad

“Me and Bobby McGee” (1970) — This towering song about a literally lost love, one of four stone-cold classics from his first album of the same name, had its final version recorded in the song by Kristofferson’s former lover, Janis Joplin, shortly before her death in 1970. While her exuberant version – which topped the Billboard Hot 100 in the months after her death – undoubtedly highlights nuances in the song that his straightforward performance doesn’t achieve, and even more poignantly, she plays with the melody like a jazz singer: “From the Kennnnn-seedy coal mines to the Cal-ifornia sun, yes Bobby shared the secrets of my soul / Through all kinds of weather, and all that we had done, yes Bobby honey, kept me from the co-wo-wold.” Kristofferson would pay her tribute on the stark “Epitaph (Black and Blue),” but the real tribute comes in giving this timeless song to her and the world. —Aswad

“The Pilgrim, Chapter 33” (1971) — Despite the apparent Biblical reference in the title, as Kristofferson says in a spoken introduction, this song is actually about some 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 wasn’t also looking in the mirror, and in what is perhaps his best vocal performance, his performance perfectly matches the endearingly debauched nature of the character he describes:

“See him lying exhausted on the sidewalk, in his jacket and jeans
Yesterday’s setbacks wear like a smile
He once had a future full of money, love and dreams
Which he published as if they were going out of fashion…’

The verses conclude:

‘But if this world continues to turn for better or for worse
And all he ever gets is older and older
From the rocking of the cradle to the rolling of the hearse
Going up was worth going down.” —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 2015 speech referenced above), it’s hard to top. But Kristofferson’s speech on this classic, probably the best musical representation ever of one hangover too many: ‘Well, I woke up Sunday morning without being able to hold my head, that didn’t hurt./ And the beer I had for breakfast was’ It wasn’t bad, so I had one more for dessert.” Kristofferson’s dry delivery perfectly embodies pain and self-loathing in the verses, but explodes in the choruses, as if in a call for redemption. —Aswad

“Why Me” (1973) — Speaking of calls to salvation, it doesn’t get much grimmer than this plea for it, a slow and mournful literal call to Jesus that apparently struck a chord with audiences in 1973, inexplicably topping the Billboard country chart and reaching No. 16 on the ranking. Hot 100. The song seemed to represent the “Sunday Morning Coming Down” character even further down a dark road: “Lord, help me Jesus, I wasted it / So help me Jesus, I know what I am / Now that I know that I need you. So help me Jesus, my soul is in Your hand.” —Aswad

“Feeling Mortal” (2013) — If there had been an unofficial sequel to “Why Me,” this song from 40 years later might have been it. Kristofferson was feeling his years when he wrote this song about the end in sight, about twelve years before it came for him. But he didn’t view the end of this life as the ultimate Sunday morning down. As anyone familiar with his catalog from the 1980s onwards probably knows, the kind of brilliant lyrical defeatism in which he specialized in his earliest writing years was not indicative of the more optimistic attitude he adopted as he settled down later in life. And so this title track from a Don Was-produced album, one of his last, was more about the feeling of gratitude than about gravity. Although not without some “shaky self-esteem” when seeing an old man in his mid-seventies in the mirror, and the always sobering realization that “here today and gone tomorrow / this is how it has to be.” And yet he addressed God (again) quite directly for someone who did not specialize in spirituality, claiming that he was grateful “from here to eternity / for the artist you are / and the man you made of me made.” Most of us can only aspire to the prospect of seeing ourselves so happy. —Chris Wilman

“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 had a No. 1 country hit with it, and it was considered such a knockout that it immediately shifted the focus back to Kris as a master songwriter. (It was pure gold for everyone; Price hadn’t had a No. 1 in 11 years before that.) Al Green had his way, too. But there is no doubt that it is a Kristofferson composition, no matter who sings 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 specific. —Wilman

“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 believes in: “Booze, broads, or a Bible… whatever helps me get through the night.” Whatever its origins, it’s a remarkably evocative song for its time, and it became something of a seduction song, covered hundreds, if not thousands, of times—so many of both, in fact, that it provided the backdrop for a skit when Kristofferson recorded “Saturday Night.” presented. Live” in 1976 (with his then wife Rita Coolidge as musical guest). While Kristofferson sings the song, Coolidge and Chevy Chase sit on a bed and look at each other in love. He tries to get the ribbon out of her hair, as the opening line goes, but can’t get it out and eventually, near the end of the song, he yanks so hard that he rips off her wig, resulting in one of Chase’s signature slapstick lines. tumbles. . —Aswad

“Please Don’t Tell Me How the Story Ends” (1978) – First of all, this is just one of the best 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 goodness he did. He was very much rocking the style of “we’re about to break up, but let’s make love first” songs in the early ’70s, and maybe that’s why he didn’t do it himself at the time, it was first recorded by Bobby Bare before he waxed it with then-wife Rita Coolidge on their third and final album of duets in 1978. Their story as a couple ended soon after… probably less romantic than the beautiful fatalism in which the song itself is shrouded. –Wilman

“Here Comes That Rainbow Again” (1982) — We can make our own picks for Kristofferson’s best songs, but when Johnny Cash said this is not only his favorite Kristofferson song, but possibly his favorite song ever, you can bet we have a spot for it will set free. Is it a family or children’s song? A raw song rooted in a Depression-induced John Steinbeck saga? All of the above? Kristofferson borrowed heavily from a chapter in “The Grapes of Wrath” to tell simple anecdotes about strangers paying it forward at a restaurant. Of course, he made this his own with one of the very best lines in his entire canon, following his descriptions of humble, almost grumpy generosity: “Ain’t it just like a human being.” That hopeful view of humanity – which of course did not characterize every song in his oeuvre, but increasingly did so – will touch you every time you hear it… and never more so than at a moment like this. —Wilman