John Prine wasn’t just a musician; he was a storyteller, a poet, and an unparalleled observer of the human condition. With a voice as raw and honest as his lyrics, he had the rare ability to find beauty in the mundane and humor in the heartbreak. From the quiet corners of small-town life to the universal struggles we all face, Prine spun tales that resonated deeply with listeners across generations. His songs were more than melodies—they were windows into the soul, capturing love, loss, hope, and everything in between.
In this article, we celebrate the legendary career of this folk and country icon by counting down his top 10 most popular songs of all time. These tracks have not only stood the test of time but also cemented Prine’s place among the greatest songwriters in history. Whether you’re a lifelong fan or discovering his music for the first time, this list will take you on a journey through the heart and humor that defined his artistry. So grab your guitar, pour yourself a cup of coffee (or something stronger), and get ready to revisit the songs that made John Prine a true American treasure. Let’s dive into the magic!
1. Angel from Montgomery (1971)
“Angel from Montgomery” stands as one of John Prine’s most beloved and enduring songs, thanks to its emotional depth and powerful storytelling. Written from the perspective of a middle-aged woman trapped in a stagnant life, the song expresses a quiet, aching desire for something more—freedom, purpose, and release. Prine’s gift as a songwriter shines through in his ability to inhabit a voice so different from his own with such empathy and grace. The central image, “Make me an angel that flies from Montgomery,” is a plea for escape, one that rings with both desperation and fragile hope. With sparse acoustic accompaniment and Prine’s weathered, honest voice, the song becomes a meditation on lost dreams and the loneliness that can settle into everyday life. Over the decades, it has been covered by many, including Bonnie Raitt, whose interpretation helped bring the song to a wider audience. Yet it’s Prine’s original version that continues to resonate for its quiet, unflinching honesty. “Angel from Montgomery” is more than just a song—it’s a vivid portrait of longing that continues to move listeners with every listen.
2. Sam Stone (1971)
“Sam Stone” is a harrowing tale of a soldier who returns home from war only to fight another battle—one against addiction and despair. With unflinching honesty, Prine tells the story of a Vietnam veteran who becomes addicted to morphine and ultimately loses everything. The line “There’s a hole in daddy’s arm where all the money goes” is among the most haunting in folk music, encapsulating the deep emotional and physical toll of war in just a few words. The song is deceptively simple in its melody, but the lyrics carry a weight that lingers long after the music fades. Prine doesn’t sensationalize or preach—he simply lays out the story with compassion and clarity, allowing listeners to draw their own conclusions. It’s this restraint and empathy that make “Sam Stone” so powerful. Released during a time when many were still grappling with the costs of the Vietnam War, the song offered a deeply personal perspective that was rarely heard in popular music. It remains one of Prine’s most impactful songs, a gut-punch of realism that continues to resonate in an era still grappling with the aftermath of war.
3. Hello in There (1971)
“Hello in There” is one of John Prine’s most emotionally stirring songs, a gentle and deeply compassionate tribute to the elderly and the forgotten. Written when Prine was just in his early twenties, the song shows a remarkable level of empathy and wisdom. He paints tender portraits of aging individuals whose vibrant lives have faded into quiet solitude, capturing the ache of being overlooked. With lines like “Old trees just grow stronger, and old rivers grow wilder every day,” Prine reminds us that age brings depth, even if society tends to ignore it. The sparse instrumentation—just voice and guitar—gives space for the lyrics to breathe, making each word land with quiet power. It’s not a sad song in the traditional sense, but one that encourages compassion and human connection. “Hello in There” urges listeners to notice those who may feel invisible and to offer a simple gesture of kindness. It has become a favorite among fans and fellow musicians alike, with countless artists covering it over the years. This song remains a testament to Prine’s ability to find profound meaning in ordinary lives and to turn that into something truly timeless.
4. Paradise (1971)
“Paradise” is both a nostalgic remembrance and a lament for what’s been lost to time and industry. Drawing on personal memories of his childhood visits to the now-vanished town of Paradise, Kentucky, Prine paints a picture of a once-beautiful place destroyed by coal mining. The refrain, “Mr. Peabody’s coal train has hauled it away,” is as much a political statement as it is a poetic image, critiquing environmental destruction with a storyteller’s grace. Despite the heavy themes, the song’s folksy charm and upbeat tempo give it a lightness that makes its message even more poignant. It’s a singalong tune that masks its sorrow in warmth and melody. The personal becomes universal, as Prine speaks not just for one town, but for countless communities across America that have faced similar fates. “Paradise” showcases his ability to combine memory, place, and protest in a way that’s both deeply personal and widely relatable. The song remains a staple of his live performances and a favorite among fans who appreciate its heart, humor, and quiet strength. It’s a timeless piece that blends environmental awareness with homespun storytelling.
5. Illegal Smile (1971)
“Illegal Smile” kicks off John Prine’s debut album with a wink and a grin, immediately setting the tone for his signature blend of wit and wisdom. On the surface, it’s a cheeky tune often interpreted as an ode to marijuana, but beneath the humor lies a clever commentary on freedom, individuality, and coping with life’s absurdities. With his trademark wordplay and mischievous sense of humor, Prine invites listeners into a world where laughter is resistance and a good chuckle can be revolutionary. The song’s bouncy rhythm and lighthearted melody make it feel almost like a singalong, but the lyrics are anything but frivolous. “You may see me tonight with an illegal smile / It don’t cost very much, but it lasts a long while,” he sings, hinting at the small pleasures that help us survive a tough world. Whether it’s about pot or just finding joy in unconventional places, “Illegal Smile” stands out for its charm and subtle depth. It’s a perfect example of how Prine could make you laugh and think at the same time—often in the very same line.
6. In Spite of Ourselves (1999)
“In Spite of Ourselves” is one of John Prine’s most endearing and entertaining songs—a duet that captures the hilariously awkward, stubborn, and sweet side of long-term love. Paired with the wonderfully offbeat Iris DeMent, Prine dives into the quirks and imperfections of a relationship that’s built on honesty, mutual tolerance, and, somehow, lasting affection. The lyrics are cheeky and unfiltered: full of colorful lines that might make you blush or laugh out loud. It’s not a polished Hollywood romance—it’s love in its most human, messy form. With its twangy, classic-country sound and homespun charm, the song feels like it could’ve been playing on a back porch radio somewhere in the heartland. Despite the lighthearted tone, there’s a lot of wisdom tucked in between the playful barbs. Prine and DeMent’s chemistry is effortless, their back-and-forth banter revealing a deep understanding of what it means to be truly seen and loved anyway. “In Spite of Ourselves” became a cult favorite, showcasing Prine’s unique gift for writing about real people and real love—warts and all. It’s the kind of song that makes you smile every time and reminds you that love, at its core, is often about laughing through the chaos together.
7. Lake Marie (1995)
“Lake Marie” is one of John Prine’s most mesmerizing and layered songs—a storytelling triumph that defies easy categorization. Named after a real lake on the border of Illinois and Wisconsin, the song blends mystery, memory, crime, and romance into one swirling, poetic narrative. It moves between three loosely connected threads: a troubled marriage, a brutal murder reported on the news, and the serene, almost magical waters of Lake Marie. The song’s structure is unconventional, with verses that unfold like spoken memories and a chorus that soars with haunting repetition: “We were standing, standing by peaceful waters.” Prine’s delivery is conversational, almost like he’s telling you a secret over a beer. Yet the effect is haunting and beautiful, with an undercurrent of sorrow and nostalgia. There’s no tidy resolution to the story, just fragments that linger in your mind long after the song ends. “Lake Marie” showcases Prine’s ability to blur the lines between truth and fiction, between journalistic detail and poetic reflection. It’s both grounded and dreamlike, strange and familiar—one of those songs that pulls you in deeper with every listen. Among Prine’s catalog, this one stands alone as a mysterious and unforgettable gem.
8. Souvenirs (1972)
“Souvenirs” is a tender, wistful reflection on memory, time, and the way we hold onto the past in small, seemingly insignificant objects. Co-written with fellow folk musician Steve Goodman, the song captures that universal feeling of longing for things that have slipped away—childhood, innocence, simpler days. Prine’s lyrics are delicate and heartfelt, painting a portrait of someone who collects souvenirs not just from places, but from moments and emotions. “Broken hearts and dirty windows / Make life difficult to see,” he sings, summing up the quiet sorrow that runs through the song. The melody is soft and unassuming, allowing the emotion in the lyrics to take center stage. There’s a gentle sadness here, but also a recognition that those memories—even the painful ones—have value. They shape who we are. The song doesn’t try to resolve that sadness; instead, it offers a kind of comfort in knowing we’re not alone in feeling it. “Souvenirs” is a reminder that while time may move on, the past is never truly lost—it lives on in the small keepsakes we carry and the stories we tell ourselves late at night. It’s a beautiful, understated jewel in Prine’s discography.
9. Fish and Whistle (1978)
“Fish and Whistle” is a buoyant, deceptively simple tune that wraps deep reflections in a bouncy, upbeat melody. It’s classic Prine: light on the surface, but full of insight if you really listen. The song talks about forgiveness, redemption, and the clumsy journey of trying to be better. With a childlike sense of wonder and a grown-up’s awareness of life’s disappointments, Prine sings about mistakes, grace, and the hope of making peace with yourself and the world. The chorus—“Father forgive us for what we must do / You forgive us, and we’ll forgive you”—is a humorous but poignant twist on the Lord’s Prayer, revealing Prine’s gift for blending the sacred and the everyday. Musically, “Fish and Whistle” has a toe-tapping rhythm that makes it easy to sing along with, even as it nudges you toward introspection. There’s joy in the music, but also humility in the lyrics—a sense that life is a mixed bag, and we’re all just doing our best. It’s the kind of song that makes you smile while sneaking in a life lesson. “Fish and Whistle” is vintage Prine: disarmingly simple, sneakily wise, and wholly unforgettable.
10. Speed of the Sound of Loneliness (1986)
“Speed of the Sound of Loneliness” is a heartbreakingly beautiful meditation on emotional distance and the quiet devastation that comes with it. Released on the album German Afternoons, the song explores the feeling of drifting apart from someone you once loved deeply. Prine’s lyrics are sparse and poetic, capturing that aching silence that follows when connection fades. “You come home late and you come home early / You come on big when you’re feeling small,” he sings, describing the confusing contradictions of a failing relationship. The title itself is a masterstroke—a poetic way of describing how quickly loneliness can set in, even when two people are still physically close. The melody is gentle but somber, perfectly matching the song’s introspective tone. There’s no blame here, just a quiet sadness and resignation. It’s the sound of love slipping through your fingers, too slow to stop but too fast to hold onto. “Speed of the Sound of Loneliness” has become a favorite for its honesty and emotional clarity, covered by many artists but always rooted in Prine’s singular voice. It’s a poignant reminder of how complex and fragile human relationships can be.
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.
