Home Music Music Lists

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.

Play video

Hiroyuki Ito/Getty Images

“All the Best” (1991)

Leave it to John Prine to turn an account of his divorce from second wife Rachel Peer into one of his most big-hearted moments, the tale of a broken heart healing itself through compassion. The song culminates in Prine’s most devastating distillation of what happens when two people grow apart: “Your heart gets bored with your mind/And it changes you.” “All the Best” anchored Prine’s 1991 comeback triumph The Missing Years, the album’s purest distillation of lost love and blossoming romance with his to-be third wife Fiona. “Having recently acquired my second divorce,” Prine said before introducing “All the Best” in 1990, “about a month later the song truck pulled up and dumped a bunch of great songs on my lawn.” In other words, he had “so much love that he cannot hide.” J.B.

Play video

David Redfern/Redferns/Getty Images

“Jesus the Missing Years” (1991)

In the Bible, there’s an 18-year gap in Jesus’ life, age 12 to 29, that’s unaccounted for. Prine decided to fill those gaps with a surreal, seven-minute, Ramblin’ Jack Elliott–style ballad. So what was Jesus up to during that time? He traveled to France and Spain, he got into some trouble with the cops, he grew his hair out, saw Rebel Without a Cause, and invented Santa Claus. Also: “He discovered the Beatles, recorded with the Stones, and once even opened up a three-way package in Southern California for old George Jones.” Jesus also meets an Irish bride, just like Prine did in the late Eighties when he met his wife Fiona in Dublin. That sequence of events ends abruptly when Jesus realizes he’s “a human corkscrew and all my wine is blood. They’re gonna kill me Mama, they don’t like me bud.”  This is why he was one of Dylan’s favorite songwriters; it’s a staggeringly beautiful piece of poetry that should be studied generations from now. P.D.

Play video

Hiroyuki Ito/Getty Images

“Lake Marie” (1995)

“Prine’s stuff is pure Proustian existentialism,” Bob Dylan once said. “Midwestern mind-trips to the nth degree.” Dylan’s favorite Prine song is a genius example of the latter. “Lake Marie” combines three different stories — one about how two lakes on the Illinois-Wisconsin border got their names, one about a failing marriage, and one about a gruesome murder — into a classic that’s part modern folk tale, part chugging, big-chorused singalong. Prine wrote about the lakes — which are real, although it’s actually Lake Mary, not “Marie” —  after consulting a local historian; the murders were inspired by grisly TV footage he remembered from his childhood. Somehow, it all comes together, light mixing with dark, shadows forming alongside the “peaceful waters” he keeps coming back to. In the middle of it all, he gets off an extremely Prine laugh line: “Many years later we found ourselves in Canada/Trying to save our marriage and perhaps catch a few fish … whatever came first.” C.H.

Play video

Andrew Lepley/Redferns/Getty Images

“In Spite of Ourselves” (1999)

Sung with Iris Dement, this he-said, she-said duet is a portrait of a long-term relationship as only Prine could write it: warm, richly detailed, and funny as hell. He talks about how she hates runny eggs, disdains money and thinks his jokes are “corny” (which he rhymes with “convict movies make her horny”); she calls out his beer-drinking and recalls that time she caught him “sniffin’ my undies.” They may not agree on much, but this is a couple that knows each other’s quirks inside and out and loves one another to the moon and back anyway. Prine wrote “In Spite of Ourselves” for Daddy and Them, a film in which he and Billy Bob Thornton played brothers. It was based, Prine said, “real loosely” on two of the movie’s characters. But its theme of warts-and-all love is universal — and a big reason it’s become a popular wedding song in recent years. C.H.

Play video

Harry Scott/Redferns/Getty Images

“Some Humans Ain’t Human” (2005)

As a songwriter who radiated kindness, generosity and humanity, Prine brings a unique sense of dispirited unbelief to this brokenhearted yet mordantly funny takedown of Republican ideology in the Bush years, released at the height of the Iraq War. “You open their hearts and here’s what you’ll find,” he sings over a spare gentle melody. “A few frozen pizzas/Some ice cubes with hair/A broken Popsicle/You don’t want to go there.” As political jeremiads go, it’s still pretty lovely, the work of an artist who could add beauty to the world even when he was singing about its ugliest people. “During Vietnam, when you saw people on the street, you knew which side they were on,” Prine said. “But you don’t know anymore. It just got to the point where if you weren’t saying anything then people were taking it that you supported him, so I thought ‘Jeez, if I get hit by a bus I would sure like the world to know that I was not a Republican.’” J.D.

Play video

Tim Mosenfelder/Getty Images

“Long Monday” (2005)

Prine’s voice was full of nostalgia and melancholy on Fair & Square, his first album after beating stage-four cancer. One of the standouts is this gorgeous ballad, written with Keith Sykes, where Prine looks back on the good times of a relationship while hinting that darkness is around the corner. “Radio’s on/Windows rolled up/And my mind’s rolled down,” Prine sings. The lyrics address a lover about to leave him alone at home for the week. But Prine was a traveling musician who didn’t like being away from his family; there’s a chance he was singing about himself. P.D.

Play video

Amy Harris/Invision/AP/Shutterstock

“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.

Play video

Mark Zaleski/AP/Shutterstock

“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.