While most people have an absolute favorite John Prine song, trying to rank his work is like trying to pick your favorite cousins at a four-generation picnic. Like all great big, tangled-up families, they all have their quirky charms, their intriguing interests, even their savory vices. How do you decide?
Prine’s people—or rather the people who populate Prine songs—add dimension to that complication. Donald and Lydia, the fading barfly, Sam Stone, the teenage unwed mother and the nurse telling her to lay down, Safety Joe, Loretta and her aging husband, Jesus in the undocumented years, and the Angel from Montgomery are just a tiny group of the characters that the Grammy and Songwriters Hall of Fame member painted with compassion and small details.
Further complicating the mission: Prine’s standards never flagged. Musical wanderlust may’ve called for different kinds of songs, but the writing remained taut and evocative; metaphors that could only come from the Midwesterner who identified as a Kentuckian and spent 40 years in Nashville, with secondary homes outside Sarasota, Florida, and his wife Fiona Whelan-Prine’s native Ireland defined his work across 14 albums of original material, as well as three live albums and a Christmas record.
Vast, wonderful, he was always embodying Francis de St-Exupery’s The Little Prince philosophy: “It is only with the heart that one can see rightly.” Here, then, are the 50 Best Prine songs (okay, really 55, but who’s counting). Whimsical, romantic, literary, simple, retrospective, forward-looking, all absolutely John Prine.
Listen to an exclusive John Prine concert from Amazingrace in 1973 while you read the list.
50. “Only Love” (Aimless Love, 1984)
With rising B3 chords and a few acoustic guitar notes, Prine almost talks to himself about how we live, what we need and how rare—but precious—love is. Somewhere between a hymn and a whispered prayer, Jim Rooney creates a dreamscape that’s as much confession as invitation. Fittingly, it serves as the final track on Aimless Love, Prine’s first independent album.
49. “Yes I Guess They Oughta Name A Drink After You” (Diamonds in the Rough, 1972)
As the fiddles saw, the acoustic guitars chum along and the dobro swivels in and out, Prine brings a bit of blues to his bluegrass. Bitter, but turned with Prine’s wordplay, the seeds of what defines Tyler Childers, Sturgill Simpsons and Kelsey Waldon were sown.
48. “Out of Love” (German Afternoons, 1986)
Only Prine could turn a beer jingle into a charming endorsement of the tenderest emotion. On German Afternoons, he makes it sound like a song to sing on a bus to summer camp.
47. “The Torch Singer” (Diamonds in the Rough, 1972)
An homage to Hank Williams that also evokes Merle Haggard, “The Torch Singer” captures a tavern where the lonely go to drink, think and hopefully burn off their own agony. Ernest and ardent, this is every working stiff’s lost hours after work: immersed in a singer who melts down their pain and torment with her songs.
46. “Everybody Wants To Feel Like You” (The Missing Years, 1991)
The existential crisis of the working Joe in a world where everything rushes by and nobody notices. “Everybody wants to be wanted…” gets to the most basic truth. But who else would say “I don’t need no transcendatilization, I don’t need no diddlybop”? or lament their once carnal delivery “I made you stutter and roll your eyes, put your mind on a brief vacation to the land of the lost surprise…” that’s been forsaken. Just, well, yes.
45. “Far From Me” (John Prine, 1971)
An impending breakup falls into a pool of steel guitar as the singer faces the inevitable with stoic resolution. Sometimes knowing what’s coming offers the ability to watch dispassionately. With nasal angst straightforward and true, Prine polishes the details, keeps his dignity and shows listeners how much it hurts. “A question ain’t really a question when you know the answer, too.”
44. “Late John Garfield Blues” (Diamonds in the Rough, 1972)
Heartfelt witness from Diamonds in the Rough, the stark portrait shows Black faces pressed against a window, the poor trying to get buy, winos, a suicide off a bridge—and a society that doesn’t seem to notice, or perhaps know what to do. The judgement is our own; Prine draws no lines but offers plenty to think about.
43. “Dear Abby” (Sweet Revenge, 1973)
Sheer nonsense! It cycles through a bunch of complaints—through the prism of nationally syndicated advice columnist Abigail Van Buren. Even funnier than the shanty-feeling reel would be when a Prine fan would actually get one of the verses published and answered in her column.
42. “People Puttin’ People Down” (Aimless Love, 1984)
Somber. He’s measuring the ones who only feel more by cutting someone else down. A sobering way to check people’s games (or your own), “People” was the sole Steve Goodman-produced track on Oh Boy’s debut Aimless Love.
41. “Christmas In Prison” (Sweet Revenge, 1973)
Somewhere between lullabye and nursery rhyme, Prine sings about the happiest night of the year in a place where no one wants to be. The chorus—pure, wonderful hillbilly braying that recalls the Hee Haw corn patch—suggests a man at peace with his circumstances; grateful for the small kindnesses, but missing the people he loves.
40. “You Got Gold” (The Missing Years, 1991)
A Johnny Cash train beat lets Prine hang all the little things that make him happy about the woman he loves on the line. A separation’s ahead as the accordions moan and mandolins tumble, but Prine weighs it all, rapturously declaring at the chorus’ end, “I got some gold inside me, too.”
39. “Your Flag Decal Won’t Get You Into Heaven Anymore” (John Prine, 1971)
Beyond impaling performative patriotism, “Flag Decal” was mail route verité. Inspired by Readers Digest—bane of mailmen everywhere—inserting flag decals into an issue, Prine suggests living your values instead of flexing a symbol without embodying the ideals.
38. “Take A Look At My Heart” (The Missing Years, 1991)
A warning to the next guy, The Missing Years’ John Mellencamp co-write that features Bruce Springsteen on vocals, “Heart” leans into Prine’s more roots-rock side. Jovial, yet to the point, it’s a rave of everything this man’s certain to hate—just wait. As a guys’ talk moment, it’s a 10.
37. “Sailin’ Around”/”Bad Boy” (German Afternoons, 1986)
Producer Jim Rooney fashioned a cloud of aural weightlessness in “Sailin’ Around,” a paean to rootlessness when one yearns for someone. German Afternoons’ slightly bashful bookend “Bad Boy” is an aw shucks reckoning of a not-so-awful rambling soul, now put on the curb, but trying to explain away what happened.
36. “Egg & Daughter Nite, Lincoln Nebraska, 1967 (Crazy Bone)” (The Tree of Forgiveness, 2018)
A little bit carny, a little bit Dixie, this thumbnail of rural life, meeting girls and hormones is a perfect sketch of a time no longer extant. Innocent, but on the prowl, Prine savors the tale on Tree’s effervescent midtempo. The song even employs mouth trombone for good measure.
35. “Let’s Talk Dirty In Hawaiian” (German Afternoons, 1986)
Bathed in tropical steel guitar, the gently chugging wordplay is equal parts novelty, hilarity and ’50s bawdiness. “Lay your coconutta on my tiki… would you like a lei” are almost childlike and perfectly clear. Originally issued as a green vinyl single, it’s Prine’s wacky side at its finest.
34. “Long Monday” (Fair & Square, 2005)
Accordion weezing, acoustic guitar plinking, the notion of the romantic hangover from a weekend of pure bliss takes Prine’s open-hearted romanticism to a reflective carnality. Modest and sincere, it speaks to what holds men and women together.
33. “Down By The Side of the Road” (Pink Cadillac, 1979)
Pink Cadillac‘s rendition is a slow loping soul mélange. A long way from the roiling boil it could be onstage when Prine toured with a band. A witness to suburban and generational unrest—with just a hint of lust tossed in—it offered a salty counter to his more country/folk ministrations.
32. “That’s The Way The World Goes ‘Round” (Bruised Orange, 1978)
The most positive just-wait song ever written. For Prine, it’s another campfire classic. In Miranda Lambert’s hands, it’s a churning cow punker. With the profession of being “naked as the eyes of a clown,” the poetry and the “it gets better” sentiment work in all kinds of arrangements.
31. “Big Ole Goofy World” (The Missing Years, 1991)
Prine believed love was a return to innocence, even butterflies in the stomach. This defines it. A carnival feeling kneads the melody as the songwriter meanders through flashcards of life, people and how they find each other. For the gruff-voiced seeker, it’s what he was seeking, too.
30. “Come Back to Us Barbara Lewis Hare Krishna Beauregard” (Common Sense, 1975)
The ’60s saw a lot of teens and 20-somethings going through gurus, communes, peyote and acid dens, free love and whatever else crossed their planes. Like “Summer’s End,” this is an invitation to a lost soul to come back home.
29. “Caravan of Fools”/”Some Humans Ain’t Human” (The Tree of Forgiveness, 2018 / Fair & Square, 2005)
His most direct, straightforward political songs. He expressed regret about taking on President Bush directly in “Human,” because being mean to people wasn’t his way. Rarely is it more tell than show.
28. “I Just Want To Dance With You” (German Afternoons, 1986)
Few souls were more romantic or quietly elegant than Prine. In a world of sexual forwardness, Prine’s old-school approach suggests something so intimate and innocent, who wouldn’t swoon? A Country Music Association Song and Single of the Year when George Strait hit #1 with it, it’s still a shriek-inducing ratification of Strait’s sex-symbol status when he plays it in concert.
27. “Spanish Pipedream” (John Prine, 1971)
“She was a level-headed dancer on the way to Montreal…” is one heckuva an opening line on the power-strumming song known by two names. John Denver recorded the wild and wooly back-to-nature life plan under the latter name, which—by default—feels like the proper title. Country star Jordan Davis used a dry vocal rendering of the chorus to set up his Country Music Association Single of the Year “Buy Dirt,” inspired by Davis’ grandfather, which speaks to its intergenerational staying power.
26. “Lake Marie” (Lost Dogs and Mixed Blessings, 1995)
A tone poem that balances two people meeting, then years later trying to save their marriage with a murder scene—all happening on the banks of a real lake on the Illinois/Wisconsin border. Lulling like waves lapping or Native Americans “wooOHHHooooh”ing, this bloomed into a major jam moment live, ultimately becoming the set closer with Prine doing his amazing shuffle dance offstage.
25. “Fish and Whistle” (Bruised Orange, 1978)
A teeter-totter rhythm lilts back and forth, as a Sisyphus quality to this fan favorite that’s as much nonsensical as it is a way to roll the mundane realities in laughter. Ironically, many of the details are true, including Prine’s job scrubbing a drive-in’s parking lot of spilled ice cream, ketchup and candy, making him a prime target of bees.
24. “I Have Met My Love Today” (The Tree of Forgiveness, 2018)
Charming, warm and from-the-heart, Prine’s gruff growl celebrates the moment of meeting his Irish bride with a melody that’s pure confectionary bliss. Drawing on Everly Brothers’ innocence and Felice and Boudleaux Bryant’s songcraft, “Met” shimmers with the best of what love is.
23. “Picture Show” (The Missing Years, 1991)
Take a stomping beat, a string of Wurlitzer blasts, a catalogue of ’50s and ’60s film stars, it’s classic Hollywood busted dreams recast as anthemic rock moment. Featuring harmonies from Tom Petty, it offers enough spunk to face the beating and somehow—even with the way the game is played—surviving the travails dinged up, but whole.
22. “Six O’Clock News” (John Prine, 1971)
Unwed mother raising the son of a man she never knew, it’s a hand-to-mouth existence in a world where people judge. It all seems like making due until the child grows old enough to splatter his brains on the sidewalk; a 1971 precursor to today’s teenage suicide crisis.
21. “Saddle In The Rain” (Common Sense, 1975)
The honking horn section, the rancor, the blistering visuals. This is Prine as a brazen soul-rocker, standing his ground. Abstract swagger in the face of feckless (girl)friend. And it blistered live.
20. “Oldest Baby In The World” (Aimless Love, 1984)
Compassion colors this lullaby to a barfly past her prime, failing to get lucky as “all of the available men seem to think they want something younger.” Written with longtime Kris Kristofferson cohort Donnie Fritts, it boasts an epic chorus of fast horses and royal flushes in a world of playing for keeps, but suggests rocking this ever-hopeful soul to sleep.
19. “Sabu Visits The Twin Cities Alone” (Bruised Orange, 1978)
Exhausted from the promo shuffle, Prine took his love of movies—and grafted his plight onto the young Indian actor who was trapped in bad “B” movies. The indignities of going into the world to flog fame were many; Prine captures them all. “Sabu must tour/ or forever rest…” is the set up, and then it all gets tragically hilarious.
18. “Speed of the Sound of Loneliness” (German Afternoons, 1986)
Perhaps the most perfect distillation of coping/not coping with being swallowed by the hole in one’s soul. It works through all the phases of trying to outrun the hollowness, traces the failed attempts and state of being “out there running just to be on the run.” But there’s a caress to his German Afternoons offering that feels like an absolution of that most vulnerable of emotions.
17. “When I Get To Heaven”/”Please Don’t Bury Me”/”He Was In Heaven Before He Died” (The Tree of Forgiveness, 2018 / Sweet Revenge, 1973 / Common Sense, 1975)
Whether Dixieland, “Blood on the Saddle”-evoking or hushed, Prine looked at the hereafter with a wink and an acceptance. To hear him sing it, what was all the fuss about? And the irony of “When I Get To Heaven” being from his final album, he paints such a vivid picture, we can trust heaven is a more joyful place with Prine in it.
16. “All The Best”/”Everything Is Cool” (The Missing Years, 1991)
The Missing Year’s divorce duo, Prine sorted through the wreckage of his broken marriage with a generosity unseen by most of us. Rather than write scornful, mournful songs, he detached with love—and provided a masterclass in how to accept what won’t be with real grace.
15. “Storm Windows”/”One Red Rose” (Storm Windows, 1980)
A pair of ballads, one stir crazy, the other glowing and hopeful, they work as bookends on Prine’s final major label release, Storm Windows. To evoke the Midwest’s dysthymic winter and yearning, as well as a collection of details that includes where the sandman sleeps, the sound of automobile wheels in the distance and a country band who plays for keeps, one feels the chill from the inside out. But it’s the romantic encounter of “One Red Rose” that counter-balances that desolation with knee-buckling intimacy.
14. “Donald and Lydia” (John Prine, 1971)
A fistful of images and sensations, as Prine drops you into moments of two unlikely people whose rejection by society sent each deep into their heads. Over more of that classic finger-picking, Prine details the motions of self-pleasure suggesting a synchronicity for fat girl and awkward army private that creates a similar illusion of romance and culmination.
13. “Illegal Smile” (John Prine, 1971)
Equal parts folk and campfire keen, which may or may not be about partaking of “the marijuana,” Prine implies it’s a smile for knowing you got away with it… which certainly covers both.
12. “Grandpa Was a Carpenter” (Sweet Revenge, 1973)
Quick strumming, it’s the perfect portrait of the grandpa everyone deserves. Working-class dignity, big fun, civic pride and a deep delight shared with his grandson, Prine’s celebration of him—and his grandmother in the final verse—are Norman Rockwell classic.
11. “In Spite of Ourselves” (In Spite of Ourselves, 1999)
Percolating rhythms set this Iris DeMent duet in a cha-cha mode, but it’s really the quirkiest of conversations between two oddball sweethearts who can’t get enough of the other. Rapacious and hilarious with awesome details, it served as the theme to Billy Bob Thornton’s “Daddy + Them,” as well as the only original song and title track to Prine’s first post-cancer release: a collection of classic country duets with many of his favorite female vocalists.
10. “Jesus, The Missing Years” (The Missing Years, 1991)
A lilting talking blues that imagined the tween/teen years of Jesus is as farflung as anything Prine ever imagined: inventing Santa Claus, recording with the Stones, a package show with George Jones, not getting a divorce in the Catholic church, children crying pork chops, a world that smelled like baby poop and “Rebel Without A Cause.” Awaking to self-knowledge for a final verse, a staggering work of imagination for something no one ever considered is a marvel.
9. “I Remember Everything” (2020)
Stunning in its simplicity, perfect in its truth. Prine, his voice husky, inhabited every moment with awareness and bliss; that deliciousness is redolent in his vocal. Here, in his final recording, he offers the song that holds dark thoughts at bay and love as his compass.
8. “Unwed Fathers” (Aimless Love, 1984)
The plight of the pregnant teenager—sent away instead of bring shame to the family—and the ability of the boy to go unseen injects pathos into this Appalachian jewel from Aimless Love. Tammy Wynette put it out as a single, but the innocence of the original—with then wife Rachel Peer—as well as the the fundraising version, following Roe v Wade’s overturning, with Margo Price—show instead of tell what the lack of accountability looks like, as well as demonstrating the inherent loving heart of a young woman and child.
7. “Souvenirs” (Diamonds in the Rough, 1972)
Providing the name for the wonderful Broken Hearts & Dirty Windows, two Oh Boy Prine tributes from alternative and younger artists influenced by his open-hearted writing, this bit of finger-picked sweetness looks at the effluvia life collects and the precious memories contained in those trivial things. It also reckons with the wear and tear of life.
6. “Hello In There” (John Prine, 1971)
Bette Midler’s piano torch Divine Miss M and Joan Baez’s bright folk Diamonds & Rust versions brought a lonely unseen older couple to the general public and helped Prine receive a Best New Artist Grammy nomination. Having walked a paper, then mail route, he watched what happened to people past their prime—and captured their abandonment hoping to raise people’s awareness.
5. “Paradise” (John Prine, 1971)
A campfire classic and bluegrass standard so familiar, generations assume it was Public Domain. A loving tribute to Muhlenberg County, where his grandparents lived; but also a scalding environmental rebuke to the strip miners who tore the countryside apart. Named in a lawsuit by Peabody Coal Co. as being prejudicial, the court stood with Prine.
4. “Mexican Home” (Sweet Revenge, 1973)
Recorded on the raucous Sweet Revenge, it evolved into a hushed finger-picked elegy that told the story of his father’s sudden death before John Prine was released. The language was lovely—“heat lightning burned the sky like alcohol”—as he traced a night stalled under an oppressive heat wave, as much a metaphor for stultifying grief as the state of an unspeakable heat spell.
3. “Angel from Montgomery” (John Prine, 1971)
Perhaps Prine’s most covered song thanks to Bonnie Raitt’s powerful delivery of this reflection from a middle-aged woman who settled and settled down. Daydreaming as she did the dishes, shipwrecked in a marriage with a man who barely speaks to her, the poignance of her emptiness—played against that rodeo cowboy she once loved—sears.
2. “Sam Stone” (John Prine, 1971)
Extended funeral organ chords waft across the Arif Mardin-produced self-titled debut’s version, reinforcing the reality of loss to addiction for many returning Viet Nam vets. It’s a stark picture of thrown-away kids, the cost of doing what was expected in a nation that refused to understand. More wars, more psychologically mutilated vets made this portrait of how life fails sadly endure.
1. “Summers End” (The Tree of Forgiveness, 2018)
Easily one of Prine’s prettiest and gentlest melodies, and it arrived on his final record The Tree of Forgiveness, showing how strong his powers remained. The craggy voice weighs the end of a dying season, creating a mournful invitation to a wayward son or friend who’s gone to return to where they’re loved. We should all have a refuge so tender and nonjudgemental.
Check out a playlist of these 50 songs below.
Holly Gleason’s work has appeared in Rolling Stone, SPIN, LA Times, NY Times, Miami Herald and NPR Music. The 2023 Southern California Media Awards’ Entertainment Journalist of the Year created, contributed and curated ‘WOMAN WALK THE LINE: How The Women of Country Music Changed Our Lives’ and co-authored ‘Y’All Eat Yet: Welcome to the Pretty B*tchin Kitchen with Miranda Lambert.’ Prine on Prine: Interviews & Encounters is her most recent work.