John Prine performing (Yellowstone National Park, YPF/Matt Ludin)

There’s a funny, spoken interlude toward the end of John Prine’s song “When I Get to Heaven,” in which Prine recalls a folksy aphorism of his Kentucky father. He delivers the line after smacking the side of his guitar, like a father might roughhouse his son: “Buddy, when you’re dead, you’re a dead pecker-head.” Prine pauses for his audience to laugh, then moseys back to the chorus. “I hope to prove him wrong,” he says, “That is, when I get to heaven.”

Prine, who died last week at seventy-three of COVID-19 at a hospital in Nashville, leaves behind a whole catalog of lines like that—heartfelt, sad, and wryly funny. He was first and foremost a narrative songwriter, and he liked to pit his characters, unpolished, hard-living middle Americans, against impossibly large foes. Sometimes, their enemies were knowable, as in the case of the coal company that leveled his ancestral Kentucky home in the song “Paradise,” or the politicians who sent so many people to their deaths in his Vietnam protest anthem “Your Flag Decal Won’t Get You Into Heaven Anymore.”

But other times, the enemy was something grander and more existential: the passage of time or death itself—the latter being a subject he was fixated on from his earliest records. “Hello In There,” his all-timer about a married couple growing old and apart, is a mournful portrait of late-age loneliness and regret, written when he was a twenty-three-year-old mailman in suburban Chicago. On “Sam Stone,” the ballad of a heroin-addicted Vietnam vet, Prine seems to dispense with redemption altogether: “There’s a hole in daddy’s arm where all the money goes / Jesus Christ died for nothin’ I suppose.”

The specter of an afterlife runs all through Prine’s work, too; over the course of a near-fifty-year career, he drew us a map of his own heaven. Its most detailed rendering is in “When I Get to Heaven,” the last track on his last album, 2018’s The Tree of Forgiveness, where Prine imagines eternally indulging in all of the vices that undid him in life: idleness, drinking, and smoking (here, the cigarettes are “nine miles long”). But his songs were replete with such visions, just as they were with heaven’s angels. A consciousness of the afterlife seemed as routine for Prine as his consciousness of mortality. On “Paradise,” a song named for his father’s Kentucky hometown, bulldozed away by a rich man’s coal company, he predicts that he’ll return to that promised land after he dies, when heaven and earth bleed together: “When I die let my ashes float down the Green River / Let my soul roll on up to the Rochester dam / I’ll be halfway to Heaven with Paradise waitin’ / Just five miles away from wherever I am.”

Prine sang about heaven as if he’d seen it, but also as if it was his own to furnish.

This isn’t the afterlife of the Christian Bible, or that of Buddhism or Islam or any other major faith. At times, it feels like a mishmash of images and ideas. On Prine’s self-titled debut album, Allah and the Buddha sing together at Jesus’ feast, while “up in the sky an Arabian rabbi / fed Quaker oats to a priest.” Of this arrangement, Prine remarks, the holy men find things are “pretty good, not bad, they can’t complain.” Really, Prine’s afterlife isn’t so unlike the place we’re in now: it’s got big hotels and community dances, oatmeal and candy bars, booze and cigarettes, familiar old rivers and his favorite shade trees. The difference is that, up there, he can have these all in abundance, and for as long as he wants them. It’s an expansive vision of heaven, and the chief comfort it offers is the brash confidence that we’ll all wind up there someday, doing most of the same things that we like to do here. Even Prine’s enemies make it in, “a few choice critics, those syph’litic parasitics.”

Prine sang about heaven as if he’d seen it, but also as if it was his own to furnish. Most of his characters don’t know what’s good for them. They drink and smoke until their organs fail. They go when they should stay and stay when they should go. They’re well-meaning but mostly directionless. None of them knows the first thing about how to wind up anything other than another dead pecker-head. Prine assures us that’s okay. Even a raunchy duet like “In Spite of Ourselves,” on its surface Prine at his most frivolous, suggests a promise of transcendence: “In spite of ourselves we’ll end up a-sittin’ on a rainbow / Against all odds, honey we’re the big door-prize / We’re gonna spite our noses right off of our faces / There won’t be nothin’ but big ol’ hearts dancin’ in our eyes.”

Prine lived through as much as anyone, returning to the stage after bouts with neck and lung cancer, surgeries that carved a distinctive dent into his neck and aged his voice by a decade. After all that, he was finally felled by the coronavirus. He spent an entire songwriting career sizing up his own mortality. His songs are filled with good people and bad people. The bad people are big, and the good usually small. Maybe there was something they could have done to prepare. But the best people in Prine’s world are all sinners, and none of them have an ounce of prescience. Somehow, they’ll end up sitting on rainbows.

Adam Willis is a freelance writer based in Washington, D.C. His work has appeared in the Boston Globe, Politico, The Outline, and Slate.

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