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John Prine: 25 Essential Songs

In his humble, hilarious way, Prine was one of America’s greatest songwriters. Here are 25 of his best – heartfelt love songs, midwestern mind-trips, and offhandedly brilliant reflections on the weird serendipity of everyday life

John Prine wrote his first two songs, “Sour Grapes” and “The Frying Pan,” when he was 14. Even at that young age, Prine could channel humor and heartbreak just like his heroes Hank Williams and Roger Miller. As he served in the Vietnam War and joined the post office as a mailman, Prine kept writing songs about his life: “Hello in There,” about the loneliness of an old empty-nest couple, the kind he encountered on his mail route, and “Sam Stone,” about a drug-addicted veteran who never really came home from the war, were just two examples. Prine wrote for working people, sad people, old people, and lost people. His style, inspired by John Steinbeck, was deceptively simple. Many emulated it, but only he could do it.

Prine, modest about his talent, didn’t give a lot of interviews. But his interview with Paul Zollo for Bluerailroad is a master class in songwriting. I think the more the listener can contribute to the song, the better; the more they become part of the song, and they fill in the blanks,” Prine told Zollo. “Rather than tell them everything, you save your details for things that exist. Like what color the ashtray is. How far away the doorway was. So when you’re talking about intangible things, like emotions, the listener can fill in the blanks and you just draw the foundation. I still tend to believe that’s the way to tackle it today.”

There’s really no such thing as a bad Prine song. Here are 25 of his best.

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“Summer’s End” (2018)

This ode to late-in-life companionship was the emotional centerpiece of  Prine’s 2018 triumph The Tree of Forgiveness. Prine opens the song with the image of swimsuits drying on a clothesline, before spinning the idea of a summer coming to a close into a metaphor for fast-approaching mortality. “Well, I don’t know, but I can see it’s snowing,” Prine sings, drawing out the last word until it becomes clear what he means. “There’s a natural sadness with that song because I do think about me and John,” his wife Fiona said in 2018. “I think, ‘OK, we have had two seasons together, and we are going into the third season.’” If Prine became famous for writing songs that could make listeners laugh at one line and cry at the next, “Summer’s End” was pure tears, with Brandi Carlile’s ghostly harmony bringing home the yearning for peace in the song’s stark “come on home” chorus. As Prine puts it in the song’s choked-up climax, “Summer’s end came faster than we wanted.” J.B.

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“When I Get to Heaven” (2018)

Prine couldn’t have written a better epitaph than this, the final song on his final album. In spoken-word verses influenced by Hank Williams’ alter-ego Luke the Drifter, Prine lays out what he will do when he reaches the pearly gates:  “When I get to heaven/I’m gonna shake God’s hand/Thank him for more blessings/Than one man can stand,” Prine sings, before laying out all he’s been grateful for: his parents, who encouraged his musical career, his departed aunts and brother Doug, and even his critics (“those syphilitic parasitics,” he says). Prine pledges to open up a nightclub called the Tree of Forgiveness in the afterlife. Over a joyous kazoo-filled chorus, he sings about making a handsome Johnny (his famous favorite drink: vodka and ginger ale) and “smoke a cigarette that’s nine miles long.” Prine had found rich subject matter in mortality for as long as he’d been recording. When he sang about his own, it was full of just as much dark humor and lyrical precision: “When I get to heaven, I’m gonna take that wristwatch off my arm,” he sang. “What are you gonna do with time/After you’ve bought the farm?” P.D.