John Prine was more than just a singer-songwriter—he was a poet of the human experience, a storyteller who could make you laugh, cry, and ponder life’s mysteries all in the span of a single song. From his early days as a mailman-turned-musical prodigy to his enduring legacy as a folk and country icon, Prine’s songs have left an indelible mark on generations of listeners. With his signature blend of wit, wisdom, and raw emotional honesty, Prine captured the beauty in life’s simple moments and the heartbreak in its complexities.
In this article, we celebrate the Top 10 most popular John Prine songs of all time—a mix of his greatest hits and fan-favorite deep cuts. These tracks showcase Prine’s unparalleled talent for crafting melodies that stay with you and lyrics that feel like they were written just for you. Whether you’re a lifelong fan or new to Prine’s music, this list is a reminder of why his work continues to resonate with audiences around the world. So grab your favorite record, settle in, and join us on a journey through the music of one of America’s most cherished songwriters.
1. Angel from Montgomery (1971)
“Angel from Montgomery” is one of John Prine’s most beloved and emotionally stirring songs, a masterclass in empathy and storytelling. Written from the perspective of a middle-aged woman stuck in a stagnant, joyless marriage, the song is a portrait of quiet desperation and yearning for something—anything—more. What’s remarkable is how Prine, a young man at the time, so convincingly steps into the shoes of someone completely unlike himself. He channels the loneliness and resignation of his character with heartbreaking detail, using vivid imagery like “a house flies in the kitchen” and “a broken radio” to evoke a sense of faded dreams and suffocating routine. The chorus—pleading for an angel to take her away—hits with raw, spiritual weight. Bonnie Raitt’s iconic cover helped bring the song to a wider audience, but Prine’s original performance carries a tender vulnerability that’s hard to match. “Angel from Montgomery” isn’t just a song about a woman’s discontent; it’s about the universal longing for escape, the ache of feeling invisible, and the hope that something better might still be out there. It’s one of those rare songs that feels like it’s always been around, and always will be.
2. Sam Stone (1971)
“Sam Stone” might be one of the most devastating songs ever written about the aftermath of war. Released on John Prine’s 1971 debut album, it tells the story of a Vietnam veteran who returns home only to be consumed by addiction and emotional numbness. With unflinching honesty, Prine documents the slow unraveling of Sam’s life—his distance from his family, his quiet descent into despair, and the toll his trauma takes not just on him, but on everyone around him. The line “There’s a hole in Daddy’s arm where all the money goes” is as stark and haunting as any lyric in American music. Prine doesn’t preach or moralize—he just lays it all out with surgical precision and heartbreaking humanity. The genius of the song lies in its simplicity; there’s no dramatic climax, just the painful reality of a man lost in a world that no longer makes sense to him. “Sam Stone” became an anti-war anthem not because it was political, but because it was personal. It gave a name, a face, and a family to the casualties we often don’t see. Even decades later, the song still hits like a gut punch.
3. Paradise (1971)
“Paradise” is John Prine’s love letter to the Kentucky of his childhood—and his lament for the way it was stripped away by industrial greed. Written for his parents and included on his 1971 debut album, the song tells the story of a town named Paradise, which was swallowed up by coal mining and ultimately destroyed by the Peabody Coal Company. But this isn’t just an environmental protest song; it’s also deeply personal. Prine remembers “the old home place,” the winding Green River, and the train that used to pass through—images that blend nostalgia with sorrow. There’s a homespun quality to the melody, and its sing-along chorus has made it a favorite at live shows and family gatherings. The refrain—“Mr. Peabody’s coal train has hauled it away”—is devastating in its simplicity, capturing the permanent loss of a place and way of life. Yet for all its sadness, the song isn’t bitter. It’s reflective, tender, and grounded in memory. “Paradise” shows Prine’s rare gift for turning a personal story into something universal. It’s about more than a town in Kentucky—it’s about the places we love, the forces that change them, and the ache of remembering what used to be.
4. Hello in There (1971)
“Hello in There” is one of John Prine’s most poignant songs, a quiet meditation on aging, loneliness, and the human need to feel seen. Written when Prine was just in his early 20s, it shows a level of emotional maturity and insight far beyond his years. The song takes the form of a gentle narrative, introducing us to an older couple whose lives have slowed to a crawl. Their children are grown, friends have passed on, and the days blur together in silence. The line “old trees just grow stronger, and old rivers grow wilder every day” is a beautiful reflection on the passage of time, filled with both reverence and melancholy. But the heart of the song lies in the simple request in its title: say hello. Prine reminds us how easy it is to walk past someone who feels invisible, and how powerful a small act of kindness can be. With just a few verses and a sparse arrangement, he turns a song into a soul-to-soul conversation. “Hello in There” isn’t just about growing old—it’s about staying human, about remembering that everyone has a story, even if they’re too tired to tell it anymore.
5. In Spite of Ourselves (1999)
“In Spite of Ourselves” is pure joy wrapped in mischief, a song that proves love doesn’t have to be perfect to be beautiful. Released in 1999 as the title track of a duet album, this cheeky and charming tune pairs John Prine with the equally endearing Iris DeMent. Together, they play a quirky couple who bicker, tease, and throw barbs at one another—but underneath it all, you can tell they’re madly in love. Prine’s lyrics are full of humor and honesty, painting a picture of a relationship that’s far from polished but full of heart. He sings about his partner’s quirks—like cooking with onions and not shaving her legs—while she claps back about his habits, from his beer belly to his wandering eye. But when the chorus hits—“In spite of ourselves, we’ll end up a-sittin’ on a rainbow”—it’s clear these two wouldn’t have it any other way. It’s a celebration of love in all its weird, wonderful messiness. More than just a novelty song, “In Spite of Ourselves” has become a fan favorite because it feels real. It reminds us that laughter, honesty, and sticking together are what make love last.
6. Illegal Smile (1971)
“Illegal Smile” kicks off John Prine’s debut album with a wink and a grin, setting the stage for the kind of songwriter he would become—clever, subversive, and joyfully offbeat. While many listeners have long assumed the song is an ode to marijuana (and let’s be honest, that interpretation’s not far off), Prine once said it was more about the ability to find happiness in the little things, even when the world feels heavy. With its rollicking rhythm and surreal humor, the song walks the line between satire and celebration. The lyrics are packed with oddball imagery and tongue-in-cheek commentary—like being arrested for “smiling on a cloudy day”—that playfully jabs at authority while championing the right to personal joy. There’s something timeless about its message: that a good laugh or a quiet moment of contentment is a kind of rebellion in itself. Whether you hear it as a stoner anthem or a metaphor for personal freedom, “Illegal Smile” is one of those songs that leaves you grinning from start to finish. It captures Prine’s genius for mixing whimsy with wisdom, showing that even the smallest smile can be a powerful thing.
7. Fish and Whistle (1978)
“Fish and Whistle,” from Prine’s 1978 album Bruised Orange, is a deceptively simple song with deep emotional resonance. On the surface, it’s about a man going through everyday life—working odd jobs, making mistakes, trying to do better. But like many of Prine’s songs, there’s a quiet depth that reveals itself the more you listen. With a bouncy, gospel-tinged melody, “Fish and Whistle” sounds almost like a hymn for the ordinary. The lyrics reflect on spiritual growth, human fallibility, and the yearning to live a life of kindness and purpose. Lines like “Father forgive us for what we must do / You forgive us, we’ll forgive you” suggest both personal humility and a subtle critique of moral hypocrisy. Prine uses humor and simplicity to explore deeper truths, and the result is a song that feels comforting and wise without ever being preachy. It’s about redemption—not in a grand, dramatic way, but in the small, daily choices we make to be better than we were yesterday. “Fish and Whistle” reminds us that grace can be found in the mundane, and that even our missteps can lead us somewhere meaningful.
8. Lake Marie (1995)
“Lake Marie,” from Prine’s 1995 album Lost Dogs and Mixed Blessings, is a song that defies categorization—it’s part love story, part murder mystery, part nostalgic reflection—and yet it all blends together into something haunting and unforgettable. The song is set near a real lake on the Illinois-Wisconsin border, but Prine uses the place as a kind of dreamlike canvas to paint memories, emotions, and eerie fragments of news headlines. The verses shift in tone and content—from fond recollections of grilled Italian sausages on the beach, to chilling reports of bodies found in the woods—all wrapped in Prine’s laid-back delivery. At first glance, the pieces don’t seem to fit. But that’s the magic of “Lake Marie”: it captures the fragmented, nonlinear way we remember things, how love and loss and fear and joy can live side-by-side in memory. The final verse—where a relationship quietly slips away—lands with unexpected emotional force. “Lake Marie” isn’t just a song you listen to; it’s one you feel your way through. Mysterious, melancholic, and weirdly beautiful, it stands as one of Prine’s most powerful examples of storytelling that’s both personal and surreal.
9. Your Flag Decal Won’t Get You into Heaven Anymore (1971)
“Your Flag Decal Won’t Get You into Heaven Anymore” is John Prine at his most satirical and sharp-witted. Written during the Vietnam War era and featured on his 1971 debut, the song is a biting critique of performative patriotism and the commercialization of national pride. Inspired by the wave of flag decals people slapped on their cars as a show of support for the troops, Prine skewers the idea that such gestures are a substitute for genuine compassion or action. With a jaunty country shuffle and a deadpan vocal delivery, he sings of a man who collects so many flag stickers that he can’t see out of his windshield—and eventually gets turned away from heaven because, well, he’s full up. The absurd humor cuts to the bone, calling out the disconnect between symbols and substance. Yet, as with most of Prine’s protest songs, there’s warmth beneath the sarcasm. He never comes off as cruel, just honest. This song remains relevant decades later, continuing to resonate with audiences navigating the ever-blurry lines between patriotism, politics, and moral accountability. It’s funny, fearless, and way ahead of its time.
10. Clay Pigeons (2005)
Though “Clay Pigeons” was originally written and performed by the late Blaze Foley, John Prine’s 2005 cover on Fair and Square brought new life to the song—and, in many ways, made it his own. Prine’s version is understated and heartfelt, a quiet meditation on loss, loneliness, and the hope of starting over. The song follows a solitary figure drifting from town to town, trying to shake off past pain and find peace in movement. With lines like “I’m going down to the Greyhound station / Gonna buy a ticket to ride,” it captures that deeply human longing for reinvention—the desire to leave behind the broken pieces and look ahead to something new, even if we don’t know what it is yet. Prine delivers the lyrics with a soft, worn-in grace that makes every word feel lived-in and true. His voice—seasoned by time and experience—adds layers of emotion to the already poignant lyrics. “Clay Pigeons” is about starting over, not with a triumphant bang, but with a quiet step forward. In Prine’s hands, it becomes a song about survival, about finding the will to keep going even when nothing makes sense.
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.
