John Prine’s music is a timeless treasure, a heartfelt blend of wit, wisdom, and raw emotion that resonates deeply with anyone lucky enough to hear it. A masterful storyteller and a pioneer of the folk and country genres, Prine’s lyrics capture the beauty and heartbreak of ordinary life with a humor and humanity that few artists can match. Whether tackling love, loss, or the quirks of everyday existence, his songs are as profound as they are relatable, offering insights that feel like they were written just for you.
In this article, we’ll take you on a journey through the top 10 most popular John Prine songs—a collection that showcases the very best of his extraordinary career. From his early masterpieces that cemented his status as a songwriting genius to the poignant gems of his later years, these tracks are a testament to his unparalleled ability to touch hearts and stir souls. Whether you’re a lifelong fan or discovering his music for the first time, this list is sure to remind you why John Prine remains one of the most beloved and influential musicians of all time. Get ready to laugh, cry, and fall in love with his music all over again!
1. “Angel from Montgomery” (1971)
Released on his self-titled debut album in 1971, Angel from Montgomery is one of John Prine’s most cherished and enduring songs. Written from the perspective of an aging woman stuck in a monotonous and unfulfilling life, the song captures themes of regret, longing, and the quiet desperation of feeling invisible. Prine’s ability to inhabit this character with such empathy and authenticity is a testament to his exceptional songwriting.
With its vivid imagery—”How the hell can a person go to work in the morning / And come home in the evening and have nothing to say?”—the song resonates with anyone who has ever felt trapped by circumstance. While Prine’s original version is deeply moving, Angel from Montgomery gained even greater prominence through Bonnie Raitt’s 1974 rendition, which brought a bluesy, soulful depth to the song.
Over the decades, Angel from Montgomery has become an anthem for those yearning for something more, whether it’s freedom, love, or simply recognition. The song’s haunting, melancholic melody combined with its poetic lyrics ensures that it remains a timeless classic, touching generations of listeners with its raw honesty and emotional depth.
2. “Sam Stone” (1971)
Sam Stone is one of John Prine’s most powerful and heart-wrenching songs, offering a brutally honest look at the struggles of a Vietnam War veteran who returns home, only to be consumed by addiction. Released on his 1971 debut album, the song is an unflinching commentary on the human cost of war, focusing not just on the battlefield, but on the lasting trauma it inflicts on soldiers and their families.
The song’s most chilling line—“There’s a hole in daddy’s arm where all the money goes”—perfectly encapsulates Sam’s tragic descent into heroin addiction. Prine’s storytelling is simple yet devastating, painting a picture of a man who once served his country but was ultimately abandoned by it. The contrast between the warm, almost lullaby-like melody and the harrowing subject matter makes Sam Stone all the more poignant.
Over the years, Sam Stone has remained one of Prine’s most celebrated works, serving as a haunting reminder of the struggles many veterans face. Its raw honesty and emotional depth have cemented it as a classic protest song, standing alongside the most powerful anti-war ballads ever written.
3. “Paradise” (1971)
A deeply personal song for John Prine, Paradise is an ode to his parents and their hometown of Paradise, Kentucky—a place ravaged by strip mining and environmental destruction. Featured on his 1971 debut album, the song is both a nostalgic tribute to his family’s roots and a lament for what was lost.
The lyrics paint a vivid picture of childhood memories, from fishing on the Green River to the sorrow of seeing the land swallowed by industry: “Then the coal company came with the world’s largest shovel / And they tortured the timber and stripped all the land.” Prine’s storytelling is so evocative that listeners can almost see the dusty roads and hear the river flowing before it was forever altered.
Musically, Paradise is a simple, heartfelt folk song, with a melody that feels as timeless as the story it tells. The song has been covered by countless artists, including bluegrass legend Tony Rice, further cementing its place as a beloved classic. Decades later, Paradise remains an anthem for environmental conservation, a testament to Prine’s ability to turn personal history into universal truth.
4. “Hello in There” (1971)
With Hello in There, John Prine crafted one of the most poignant songs ever written about aging and loneliness. Featured on his debut album, the song tells the story of an elderly couple whose children have moved away, leaving them isolated in their later years. The refrain—“Hello in there, hello”—is a plea for connection, urging listeners to recognize and acknowledge the elderly instead of letting them fade into the background.
Prine’s lyrics are deeply empathetic, offering intimate glimpses into the lives of people who feel forgotten. Lines like “We lost Davy in the Korean War / And I still don’t know what for” add an extra layer of sorrow, touching on grief and the passage of time. The song’s gentle melody, combined with Prine’s heartfelt delivery, makes it an emotionally stirring experience.
Over the years, Hello in There has remained one of Prine’s most beloved songs, covered by artists like Joan Baez and Bette Midler. It serves as a timeless reminder of the power of human connection, urging us all to take a moment and truly see those around us.
5. “In Spite of Ourselves” (1999)
A delightful departure from John Prine’s more melancholic works, In Spite of Ourselves is a playful and irreverent duet featuring Iris DeMent. Released in 1999 on the album of the same name, the song is a celebration of love in all its quirky, imperfect glory.
With witty lyrics like “She thinks all my jokes are corny / Convict movies make her horny,” Prine captures the charm of real-life relationships—flawed, funny, and completely unfiltered. The chemistry between Prine and DeMent is undeniable, making the song feel like a conversation between two people who truly know and adore each other, despite their oddities.
The song’s country-tinged melody adds to its warmth, giving it an old-timey feel that makes it stand out in Prine’s catalog. In Spite of Ourselves quickly became a fan favorite, often played at weddings and anniversaries as a testament to enduring love. It’s a reminder that romance isn’t about perfection—it’s about embracing each other’s weirdness and loving each other all the more for it.
6. “Illegal Smile” (1971)
As the opening track on John Prine’s debut album, Illegal Smile showcases his unique blend of humor and social commentary. The song’s lighthearted melody and witty lyrics, often interpreted as a subtle nod to marijuana use, mask the deeper reflection on the complexities of life. Prine’s irreverence shines through as he navigates themes of escapism, frustration, and self-awareness, all while maintaining a playfully upbeat tone.
The song’s famous opening line—“I really don’t mind if you sit this one out”—sets the tone for its laid-back feel, suggesting that the narrator is content to enjoy life on his own terms, regardless of the opinions of others. With clever wordplay and a catchy melody, Illegal Smile captures Prine’s knack for turning seemingly light subjects into profound reflections on human nature.
While the song is often associated with its cheeky references to marijuana, it’s really about the way people cope with the pressures and challenges of life. The refrain “I’m gonna take me a puff / Gonna sit back and enjoy myself” serves as a reminder that, sometimes, the best way to handle life’s absurdities is simply to smile and enjoy the ride. Over the years, Illegal Smile has become a fan favorite for its catchy tune and Prine’s unpretentious approach to life.
7. “Fish and Whistle” (1978)
Released in 1978 on his album Bruised Orange, Fish and Whistle is one of John Prine’s most enduringly joyful tracks. The song combines upbeat, sing-along energy with themes of redemption and forgiveness. Its catchy melody and whimsical lyrics make it a delightful tune, but beneath the surface, it offers a message of personal growth and the importance of self-reflection.
In Fish and Whistle, Prine uses his trademark humor to discuss the sometimes absurdities of life. The song’s quirky refrain—“Fish and whistle, whistle and fish / Eat everything that they put on your dish”—speaks to a simple but important philosophy: to accept what comes and move forward with a sense of humor.
The song also touches on themes of faith and renewal, with lines like “The Lord is my shepherd, He goeth before me.” It’s a reflection on the idea that even in the face of life’s challenges, there’s room for redemption, for joy, and for laughter. Fish and Whistle continues to resonate with fans for its uplifting message, reminding us that redemption and forgiveness are always within reach, no matter how complicated life can be.
8. “Lake Marie” (1995)
Lake Marie, from John Prine’s 1995 album Lost Dogs and Mixed Blessings, is a mesmerizing blend of storytelling and mystery. The song weaves together different narratives, from the peaceful setting of a lake to the tragic story of a love gone wrong, creating a multi-layered tale that engages the listener’s imagination. Prine’s ability to intertwine personal history with universal themes is evident throughout this track.
The song’s shifting perspectives—from the serene beauty of Lake Marie to the haunting tales of lost love—add to its allure. The lyrics, rich in detail and emotion, create vivid imagery that brings the setting to life. “Heard about a lake in a land of pure delight,” Prine sings, and suddenly, we’re transported to a quiet place where love, loss, and mystery all converge.
What makes Lake Marie especially compelling is its ability to remain both introspective and universal. It’s a song about longing, about searching for meaning in the complexity of life, all set against the backdrop of a tranquil but enigmatic lake. The song’s hypnotic rhythm and Prine’s evocative storytelling make Lake Marie one of his most celebrated and enigmatic tracks, offering a hauntingly beautiful experience for listeners.
9. “Souvenirs” (1972)
Souvenirs, from John Prine’s 1972 album Diamonds in the Rough, is a bittersweet reflection on the passage of time and the memories we collect along the way. The song is a tender exploration of nostalgia, capturing the feelings of loss and longing that often accompany aging. Through his delicate lyrics and understated melody, Prine conveys the emotional weight of holding on to the past while accepting that it inevitably slips away.
The song opens with the line, “I’ve got a souvenir of the city,” setting the stage for a meditation on how memories, like keepsakes, are sometimes all we have left. The refrain—“And the older I get, the better I was”–is a poignant acknowledgment of how we often romanticize the past as we grow older, with a mixture of fondness and regret.
Despite its melancholic themes, Souvenirs is not without hope. Prine’s delivery is soft but reassuring, giving the listener a sense that the memories we hold are valuable in their own right, even if they can’t be relived. The song’s simplicity and emotional depth have made it a favorite among fans who see themselves reflected in its tender exploration of time, memory, and acceptance.
10. “Clay Pigeons” (2005)
Released in 2005 on his album Fair & Square, Clay Pigeons is John Prine’s haunting and soulful cover of Blaze Foley’s original song. Prine takes Foley’s story of redemption and starting over and breathes new life into it with his signature warm, gravelly voice and gentle delivery. The song reflects on the struggles of beginning again, finding meaning in life, and letting go of the past in search of something better.
Prine’s rendition of Clay Pigeons is understated yet powerful, as he navigates the emotional landscape of loss, hope, and resilience. The lyrics, with lines like “I’m going to let the world go by,” suggest a deliberate stepping back from the chaos of life to find peace in simplicity and personal growth.
What stands out in Prine’s version is the depth he brings to Foley’s original song. His gravelly voice lends a weathered authenticity to the lyrics, making it feel like a conversation between two kindred spirits. Clay Pigeons speaks to anyone who has ever tried to leave behind their past, while still carrying its weight, in order to move forward with purpose and clarity. Through Prine’s interpretation, this song has become a touching meditation on life’s ability to offer new beginnings, even amidst hardship.
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.
