Johnny Cash, Janis Joplin, Al Green, and Sammi Smith all had career-defining hits with Kristofferson’s songs. But none match the lonesome intimacy of his own versions.

Country music is full of odd gents with peculiar backgrounds, but it seems safe to assume that Kris Kristofferson is the only legend whose resumé includes a Rhodes Scholarship, a stint flying helicopters, an apprenticeship as a Nashville janitor, and major movie stardom at a time when a man could still look like he hadn’t bathed in years and still register as a big-time sex symbol. But don’t hold Kristofferson’s gift for erudition against him: at his most plaintive and powerful, his songs boast a primal directness to rival Hank Williams.

Equal parts willfully cryptic and straightforward, Kristofferson’s “Me and Bobby McGee” condenses a novel’s worth of heartbreak and loss into four minutes and 23 seconds of high lonesome. Kristofferson’s characters are forever trying to steal bits of happiness and connection from a world that tears people apart, from each other and their better angels.

Kristofferson wielded simplicity like a hobo’s switchblade, but a desperate yearning for connection, if only for one night, courses through his songs, most notably “Help Me Make It Through the Night.” There’s something almost feminine about the song’s raw, yearning nakedness. He might reek of whiskey and gasoline, but his drifters nevertheless pine for the intoxicating scent of a woman’s perfume and the softness of her touch.

But Kristofferson’s most enduring triumph is its closing song, “Sunday Mornin’ Comin’ Down,” which is full of the kind of plainspoken truth and novelistic details that distinguished the music of The Velvet Underground. It begins slow and sad, the sonic equivalent of the kind of hangover that feels both like fearsome retribution from a vengeful deity and a migraine that will last for all of eternity.

Kristofferson narrates this bleary, almost unbearable torment with the kind of good humor that is his only consolation, reckoning that the beer he had for breakfast wasn’t bad so he had one more for dessert. We then move to the city streets, where children are playing, oblivious to his pain or anything but their own half-hearted amusement. It is at this point that a folky ramble takes on a mythic, overpowering quality as the mundane but perfectly chosen details in the song build slowly but eloquently to a wish for “A Sunday morning sidewalk, wishing lord that I was stoned, because there’s something in a Sunday that makes a body feel alone.”

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It’s all there: the juxtaposition of the sacred (Sunday morning, wishing, songs from a nearby church) and the profane, and a loneliness that you can feel in your bones. For this champion sinner, Sunday is a day of special torment, a time when lost souls like himself ache for a transcendence they’ll always pine for and never achieve.

It is, like the best of Kristofferson, a drunkard’s shambling gospel and in one song Kristofferson not only delivered the single greatest hangover song of all time but also established himself as an artist, a poet whose erudition was more at home at Tootsie’s Orchid Lounge or some fetid whorehouse than his alma mater Oxford. Kristofferson, and particularly “Sunday Mornin’ Comin’ Down,” told the world exactly who he was: equal parts poet and working man, sinner and holy man, stumbling and fumbling and never quite achieving the grace he so desperately pined for.