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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 at an apartment on Briarcliff Road during John Prine on campus of Georgia State College - November 12, 1975 at Georgia State College in Atlanta, Georgia, United States. (Photo by Tom Hill/WireImage)

Prine in 1975.

Tom Hill/WireImage

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.

Musician John Prine on stage, circa 1970-1975. (Photo by Tony Russell/Redferns/Getty Images)

Tony Russell/Redferns/Getty Images

“Blue Umbrella” (1973)

Prine wrote this young man’s blues about an early breakup, the same one that inspired his debut album masterpiece “Far From Me.” “The first time you get your heart busted, you never forgive,” he said years later. “Especially if you’re a writer.” The song was part of Prine’s earliest repertoire in Chicago folk circuit, but he hung onto it for a while, making it a downcast highlight of his third album, 1973’s Sweet Revenge. In this two-verse torch song, young heartbreak is recast as a torrential storm, and Prine is left with only a sad umbrella to “hide the pain while the rain makes up [his] mind.” But “Blue Umbrella” will always be remembered for its chorus, with its unforgettable depiction of feeling young, lost, and alone: “Just give me one extra season,” Prine begs. “So I can figure out the other four.” J.B.

NASHVILLE, TN - 1981:  Singer/songwriter John Prine lights up a cigarette in his hotel room during a 1981 Nashville, Tennessee, portrait session. Prine created his own record label "Oh Boy Records" after being dropped by Asylum in 1980, eventually winning a Grammy for the 1991 album "The Missing Years". (Photo by George Rose/Getty Images)

George Rose/Getty Images

“Bruised Orange (Chain of Sorrow)” (1978)

This dark surrealist tale is based on Prine’s real-life traumatic childhood memory of witnessing the aftermath of a local altar boy who was killed by an Illinois commuter train. Prine juxtaposed the violent tale, which both opens and closes the song, with an unusually anthemic chorus (inspired by Bob Dylan’s “The Lonesome Death of Hattie Carroll”) about fighting against our worst tendencies and a seemingly unrelated second verse about kissing a black-haired girl on a park bench. “My head shouted down to my heart, ‘You better look out below,’” he sang. “When I’m writing, I’m never sure if it’s really facts I’m getting or if I’m making it up,” the songwriter said in 2017. “There’s no line.” Years after Prine released the song, the parents of the altar boy sent Prine a letter thanking him for it. J.B.

Musician John Prine performs on stage at the Park West in Chicago, Illinois, September 23, 1978. (Photo by Paul Natkin/Getty Images)

Paul Natkin/Getty Images

“Fish and Whistle” (1978)

On this upbeat stomper off Bruised Orange, his excellent, undersung third album, Prine combines snapshots from various different chapters of his life – from his first job working at a local drive-in to his army days – and strings them together with a chorus about the importance of forgiveness. The song is full of hilarious observations pulled straight from real life. “On my very first job I said ‘thank-you’ and ‘please’/They made me scrub a parking lot down on my knees/Then I got fired for being scared of bees/And they only give me fifty cents an hour.” Prine admitted after writing the song that he indeed was terrified of bees. P.D.

NASHVILLE, TN - 1981:  Singer/songwriter John Prine poses in his hotel room during a 1981 Nashville, Tennessee, portrait photo session. Prine created his own record label "Oh Boy Records" after being dropped by Asylum in 1980, eventually winning a Grammy for the 1991 album "The Missing Years". (Photo by George Rose/Getty Images)

George Rose/Getty Images

“It’s Happening to You” (1980)

Not a literary masterpiece, just a compact, easygoing tune that seems to effortlessly sum up the life cycle of a relationship from first kiss to last goodbye with a perfect mix of matter-of-fact honesty and genuine wonder at the cheesy depth of the ritual. “You know what they say/They pledge their love forever/Then they add a day,” he sings, proudly adding his own two cents to one of pop music’s richest songwriting traditions. Rachel Peer’s subtle harmony vocals give the song an extra shading of bittersweet beauty. J.D.

Musician John Prine performs on stage at the Aire Crown Theater in Chicago Illinois,  January 26, 1985. (Photo by Paul Natkin/Getty Images)

Paul Natkin/Getty Images

“Unwed Fathers” (1984)

Prine wrote this tale of the double standards facing a single pregnant mother with legendary Nashville songwriter Bobby Braddock in the early eighties. “I wrote down 15 titles, including one called ‘Children Having Children’ and ‘Unwed Fathers’” Prine later said. “I was reading the list off to him, and all the lights went on with those two. We kind of combined them and went right into it.” The song, later recorded by Tammy Wynette and Johnny Cash, was the highlight of his 1984 album Aimless Love, where Prine sang it as a duet with then-wife Rachel Peer. In later years,it became a duet standard for Prine, who would perform it with friends like Margo Price, Iris DeMent and Amanda Shires. J.B.

Musician John Prine performs on stage at the Aire Crown Theater in Chicago Illinois,  January 26, 1985. (Photo by Paul Natkin/Getty Images)

Paul Natkin/Getty Images

“Let’s Talk Dirty in Hawaiian” (1986)

Written on the patio of a Nashville hotel and released on Prine’s 1986 album German Afternoons, “Let’s Talk Dirty in Hawaiian” is at once one of the greatest vacation songs and one of the greatest sex songs ever written — pure playful fun stuffed with wonderful, hilarious wordplay. “It’s a ukulele Honolulu sunset.” Prine sings against inviting geographically appropriate accompaniment, “Listen to the grass skirts sway/Drinking rum from a pineapple/Out on Honolulu Bay/The steel guitars all playing/ While she’s talking with her hands/ Gimme gimme oka doka make a wish and wanta polka/Words I understand, hey!” He described it as “the kind of song that keeps you out of the shrink.” J.D.

Musician John Prine performs on stage at Farm Aid 2 in Austin, Texas, July 4, 1986. (Photo by Paul Natkin/Getty Images)

Paul Natkin/Getty Images

“Speed at the Sound of Loneliness” (1986)

Written in the aftermath of a bad relationship, this 1986 ballad is John Prine at his most romantically destitute. “It was a song about a break up,” he said in 2016. “I had a picture in my mind of one of the astronauts of the 1950s with his face all contorted by G-force. I was thinking of somebody’s heart being pulled apart by G-force like that.” Just as “Angel From Montgomery” became best known from Bonnie Raitt’s rendition, “Speed of the Sound of Loneliness” belonged to Nanci Griffith, who included a duet of the song with Prine on her 1993 album Other Voices, Other Rooms. But the simple three-chord devastation in this tale of two lovers who’ve grown far, far apart was pure Prine, resulting in perhaps the most heartbreaking line in his songbook: “You come home straight/And you come curly,” he sang. “Sometimes you don’t come home at all.” J.B.

American singer John Prine on stage at the Cambridge Folk Festival, England, August 2nd 1992. (Photo by Dave Peabody/Redferns/Getty Images)

Dave Peabody/Redferns/Getty Images

“The Sins of Memphisto” (1991)

Written at the last minute as he wrapped up work on his 1991 LP, The Missing Years, “Sins of Memphisto” is a lovely, laidback literary tour-de-force full of classic rhymes (“Sally used to play with here Hula Hoops/ Now she tells her problems to therapy groups”), absurdist imagery and careful everyday observation, spun into a beautiful meditation on love and aging, youthful freedom and lost innocence. The song’s cast of characters include Adam and Eve, Lucile Ball and Ricky Ricardo, Esmeralda and the Hunchback of Notre Dame, a kid riding his bike around a town he can’t wait to escape and a Grandpa “on the front lawn staring at a rake/Wondering if his marriage was a terrible mistake.” It’s all delivered with the a tender late-afternoon prettiness that makes its uncomfortable realizations about life go down like a sip of Orange Crush. J.D.

John Prine performing at Town Hall on Thursday night, September 16, 1999.(Photo by Hiroyuki Ito/Getty Images)

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.

NEW ORLEANS - MAY 04 : John Prine performs on stage at the New Orleans Jazz and Heritage Festival in New Orleans, Louisiana on May 04,1990. (Photo by David Redfern/Redferns)

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.

John Prine performing at Town Hall on Thursday night, September 16, 1999. (Photo by Hiroyuki Ito/Getty Images)

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.

UNSPECIFIED - CIRCA 2000:  Photo of John PRINE  (Photo by Andrew Lepley/Redferns)

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.

UNITED KINGDOM - OCTOBER 28:  PALLADIUM  Photo of John PRINE, John Prine performing on stage, acoustic guitar  (Photo by Harry Scott/Redferns)

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.

AUSTIN TX - SEPTEMBER 23: John Prine performs as part of the Austin City Limits Music Festival at Zilker Park on September 23, 2005 in Austin Texas. (Photo by Tim Mosenfelder/Getty Images)

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.

John Prine performs at the Bonnaroo Music and Arts Festival, in Manchester, Tenn2019 Bonnaroo Music and Arts Festival - Day 3, Manchester, USA - 15 Jun 2019

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.

John Prine performs during the Americana Honors and Awards show, in Nashville, TennMusic Americana Awards, Nashville, USA - 12 Sep 2018

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.

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