Few artists have the ability to capture the essence of humanity like John Prine. With his sharp wit, heartfelt storytelling, and unparalleled ability to find beauty in the mundane, Prine carved a unique space in the world of folk and country music. His songs are more than just melodies—they are windows into life’s tender moments, its ironies, and its bittersweet truths. Whether he’s making you laugh with clever wordplay or bringing you to tears with poignant reflections, Prine’s music resonates across generations.
In this article, we’re diving into the top 10 most popular John Prine songs of all time. These tracks aren’t just fan favorites—they’re masterpieces that showcase the depth and versatility of his craft. From intimate ballads that tug at your heartstrings to foot-tapping anthems steeped in humor and social commentary, these songs highlight why Prine remains a beloved icon in the music world.
Whether you’re a lifelong fan or discovering his music for the first time, this list celebrates the greatest hits of a storyteller who had the rare gift of turning the ordinary into the extraordinary. So grab a seat, press play, and let John Prine’s timeless music take you on a journey you’ll never forget.
1. Angel from Montgomery (1971)
“Angel from Montgomery” is one of those rare songs that feels like it’s always existed. Released on John Prine’s self-titled 1971 debut, it’s a poignant character sketch told from the perspective of a middle-aged woman stuck in a life of quiet desperation. The power of the song lies in Prine’s remarkable empathy—he steps completely into the shoes of someone utterly different from himself and tells her story with grace, restraint, and heartbreaking honesty. “I am an old woman named after my mother,” the first line begins, and from there, it’s a slow unraveling of dreams deferred and years lost. The refrain, “Make me an angel that flies from Montgomery,” is both a plea for escape and a sigh of surrender. There’s something timeless about the melody and the simplicity of the chords, and it’s no wonder Bonnie Raitt’s haunting cover brought it to even wider audiences. But Prine’s original version, with its understated vocals and matter-of-fact sorrow, remains untouchable. It’s not just a song—it’s a window into someone’s soul, a quiet anthem for anyone who’s ever felt invisible in their own life.
2. Sam Stone (1971)
“Sam Stone” might be one of the most gut-wrenching songs ever written about the toll of war and addiction. Featured on Prine’s 1971 debut, it tells the story of a Vietnam veteran who returns home to a world that no longer makes sense, turning to drugs to numb the pain. The song’s most unforgettable line—“There’s a hole in daddy’s arm where all the money goes”—hits like a punch to the gut, especially when delivered in Prine’s unflinching, plainspoken style. What makes “Sam Stone” so powerful is its refusal to romanticize or sensationalize. Prine presents his character with heartbreaking honesty and empathy, never judging, just observing. The storytelling is clinical in detail but deeply human in tone, tracing the arc of Sam’s decline from war hero to forgotten man. It’s a song that made people stop and pay attention, cementing Prine’s reputation as a fearless chronicler of the human condition. In under four minutes, he tells a complete life story that speaks volumes about trauma, neglect, and the quiet tragedies playing out behind closed doors. Even decades later, it hasn’t lost an ounce of its emotional weight.
3. Paradise (1971)
“Paradise” is a homesick, bittersweet tribute to a place that no longer exists—at least not in the way it once did. Written for his parents, who were from Muhlenberg County, Kentucky, the song laments the environmental destruction caused by strip mining, particularly by the Peabody Coal Company. But Prine doesn’t preach. Instead, he sings with the voice of someone who simply misses the green banks of the Green River, where he once skipped stones and spent time with family. The chorus, with its plea to “take me back to Muhlenberg County,” captures the kind of nostalgia that hits deep—the longing not just for a place, but for a time and a feeling. It’s a personal story wrapped in a broader environmental message, and that’s what makes it so effective. Prine’s gift was in turning politics into poetry without ever sounding preachy. “Paradise” has become an anthem for anyone who’s watched their hometown change beyond recognition or disappear entirely. Whether you’ve been to Kentucky or not, the ache in the song is universal. It’s a song of memory, of loss, and of the quiet rage we carry when the places we love are taken from us.
4. Hello in There (1971)
“Hello in There” is John Prine at his most tender and observant. On a debut album filled with deeply empathetic songs, this one stands out for its quiet heartbreak. It’s a ballad about aging, loneliness, and the invisibility that often comes with growing old. Prine sings from the perspective of an elderly couple whose children have moved away and whose days now stretch out in silence. “Old trees just grow stronger / And old rivers grow wilder every day,” he sings, using natural imagery to express the quiet, internal power of people society tends to overlook. What’s remarkable is how much compassion Prine packs into every line. The song doesn’t wallow in sadness—it asks for kindness, for people to take the time to really see one another. “So if you’re walking down the street sometime / And spot some hollow ancient eyes / Please don’t just pass ’em by and stare / As if you didn’t care.” It’s a gentle request, one that lingers long after the song ends. “Hello in There” feels like a conversation with your grandparents, or your future self. It’s a reminder that everyone has a story, and that sometimes, all someone needs is to be acknowledged.
5. Illegal Smile (1971)
Kicking off his debut album with a wink and a grin, “Illegal Smile” introduces us to Prine’s whimsical side—though, true to form, there’s more going on beneath the surface. While often assumed to be about marijuana (and it definitely nods to the counterculture of the time), Prine once said it was more about finding happiness in unexpected places. The lyrics are clever and surreal, painting little vignettes of absurdity: dogs named “Chevy,” train rides that go nowhere, and winks at the listener that break the fourth wall. “You may see me tonight with an illegal smile,” he sings, with a mischief that never grows old. It’s a song that feels like a protest and a lullaby rolled into one—a gently rebellious tune that reminds us not to take everything too seriously. The melody skips along, and the live versions are even more fun, often getting chuckles and cheers from audiences who love being in on the joke. “Illegal Smile” is Prine the prankster, the poet, the guy who saw the world sideways and found joy in the tilt. It’s a brilliant opening statement for a debut album, hinting at the layered storytelling to come.
6. Lake Marie (1995)
“Lake Marie” is one of those songs that defies easy explanation—but that’s exactly what makes it such a John Prine masterpiece. Released in 1995 on his album Lost Dogs and Mixed Blessings, the track is a swirling blend of memory, mythology, and mystery, anchored by a real-life lake on the border of Wisconsin and Illinois. Prine stitches together three seemingly unrelated threads: a failing marriage, local folklore, and grisly news reports of murder. On paper, it sounds chaotic—but in Prine’s hands, it becomes poetry. His voice cracks with emotion, especially in the line “We were standing, standing by peaceful waters,” which repeats like a prayer or an echo from a dream. The song is both grounded and surreal, flipping between spoken-word verses and a melodic chorus that feels like a refrain from another lifetime. It’s one of his most cinematic tracks, conjuring images that are eerie, romantic, and nostalgic all at once. The beauty of “Lake Marie” lies in its refusal to fully explain itself. Like the best stories, it gives you just enough to feel something deeply—even if you can’t quite name it. It’s haunting, funny, heartbreaking, and unforgettable. In short, it’s pure Prine.
7. In Spite of Ourselves (1999)
“In Spite of Ourselves” is John Prine at his funniest, flirtiest, and most human. Released in 1999 as the title track of his duet album with Iris DeMent, this charming country love song celebrates the quirks and imperfections that make relationships real. With lines like “She don’t like her eggs all runny / She thinks crossin’ her legs is funny,” Prine paints a vivid picture of a couple that might be mismatched on paper but fits together in the ways that count. Iris DeMent’s warm, twangy voice is the perfect foil to Prine’s weathered drawl, and their chemistry is undeniable. They sing like two people who have seen it all, laughed through the mess, and still show up for each other every day. What makes the song so special is its honesty—it doesn’t romanticize love as something smooth or ideal. Instead, it celebrates the messy, awkward, enduring stuff: the inside jokes, the weird habits, the tender barbs. “In Spite of Ourselves” feels like listening in on a kitchen-table conversation between two people who’ve learned to love each other not despite their flaws, but because of them. It’s hilarious, heartfelt, and wildly relatable.
8. Speed of the Sound of Loneliness (1986)
“Speed of the Sound of Loneliness” is one of those songs that sneaks up on you. Released on German Afternoons in 1986, it’s a slow-burning meditation on emotional distance—how two people can share space but feel galaxies apart. The title itself is pure poetry, suggesting a kind of quiet hurt that moves faster than we expect and hits deeper than we realize. Prine’s voice is weary but resolute as he sings, “You’ve broken the speed of the sound of loneliness / You’re out there running just to be on the run.” The song doesn’t shout its sadness—it lets it seep in, line by line. There’s a kind of resignation in the melody, like someone who’s come to terms with a loss that won’t ever fully heal. Though it’s melancholy, it’s never bitter. Prine delivers each line with a sense of knowing that makes you feel less alone in your own heartbreak. Over the years, the song has been covered by artists like Nanci Griffith and John Denver, but there’s something about the original version—its gentle steel guitar, its honest ache—that makes it timeless. It’s loneliness captured in slow motion.
9. Fish and Whistle (1978)
“Fish and Whistle,” from Prine’s 1978 album Bruised Orange, is like a hymn for the ordinary and the odd. With its bouncy melody and gospel-like chorus, the song offers a quirky mix of faith, forgiveness, and frustration. It starts with Prine praying to God to “forgive us our trespasses” and then launches into a story about hitchhiking, getting fired from a bakery, and trying to make sense of a chaotic world. But beneath the humor and playful rhymes lies a deeper message: the importance of hope, second chances, and carrying on even when life feels absurd. “Father, forgive us for what we must do / You forgive us, we’ll forgive you,” he sings, walking that fine line between reverence and rebellion. It’s one of those songs that makes you smile even as it points to something true and a little painful. Prine had a gift for wrapping serious ideas in silly packaging, and “Fish and Whistle” is a perfect example. It’s funny, wise, and totally singable—a reminder that life is a weird ride, but if you keep your sense of humor (and maybe a harmonica handy), you’ll make it through just fine.
10. Clay Pigeons (2005)
Though John Prine didn’t write “Clay Pigeons”—that honor belongs to the late, great Blaze Foley—his 2005 cover on Fair and Square feels like a perfect fit. Prine takes the already-beautiful song and gives it a quiet, knowing depth, as if he’s lived every line. The song follows a narrator who’s trying to start fresh—boarding a Greyhound, leaving the past behind, and trying to find peace somewhere down the line. “I’m goin’ down to the Greyhound station / Gonna get a ticket to ride,” he sings, with a kind of soft defiance, a hope that maybe things can still be different. Prine’s delivery is gentle, weathered, and full of empathy. He doesn’t try to polish the song—he just lets it breathe. There’s a subtle warmth in the way he sings about wanting to talk to strangers and be kind, like he understands the craving for connection in a world that often feels disconnected. “Clay Pigeons” is a song about motion, about letting go, and about the strange comfort of solitude. Prine made it his own not by changing it, but by simply being present in it—just as he did with every song he ever touched.
Edward Tomlin is a frequent contributor to Singers Room. Since 2005, Singersroom has been the voice of R&B around the world. Connect with us via social media below.
