Few artists have the ability to capture the raw beauty of life’s simplest and most profound moments like John Prine. Revered as one of the greatest songwriters of his generation, Prine’s music resonates with humor, heartbreak, and humanity. His songs, often crafted with a storyteller’s precision and a poet’s soul, paint vivid portraits of everyday struggles, fleeting joys, and the bittersweet complexity of love. Whether you’re a lifelong fan or just discovering his genius, this journey through his most popular songs is a testament to the enduring legacy of his artistry.
From the poignant reflections of “Angel from Montgomery” to the tongue-in-cheek wit of “Dear Abby,” Prine’s catalog is a treasure trove of emotional depth and storytelling brilliance. These are songs that have not only stood the test of time but have also touched the hearts of generations. In this article, we’ll count down the top 10 John Prine songs that have left an indelible mark on the world of music. So, grab your favorite record, settle in, and prepare to revisit (or discover) the songs that showcase why John Prine’s music will forever remain timeless. Let’s dive into the melodies and lyrics that made him a legend.
1. “Angel from Montgomery” (1971)
John Prine’s “Angel from Montgomery” is a beautifully sorrowful ballad that captures the quiet desperation of a woman trapped in a monotonous life. Released on his 1971 self-titled debut album, the song tells the story of an aging woman who reflects on the dreams she once had and the reality she now faces. With poignant lines like “How the hell can a person go to work in the morning, come home in the evening and have nothing to say?”, Prine paints a vivid portrait of loneliness and longing.
The song’s aching refrain— “Make me an angel that flies from Montgomery”—acts as both a plea for escape and a poetic expression of hopelessness. Its folk-country melody and restrained instrumentation allow the lyrics to take center stage, letting the emotions seep through in every line. While Prine’s original version is stunning, Bonnie Raitt’s 1974 cover introduced the song to a wider audience, solidifying its status as one of the greatest American folk songs ever written.
Despite its personal narrative, “Angel from Montgomery” resonates with people across generations, making it an enduring anthem for those who feel stuck, yearning for something more. Prine’s gift for storytelling shines in this classic, proving why his songwriting is so deeply cherished.
2. “Sam Stone” (1971)
Few songs capture the devastating impact of war like John Prine’s “Sam Stone.” Released in 1971, this harrowing ballad tells the story of a Vietnam War veteran who returns home physically alive but emotionally and spiritually broken. Through the lens of Sam Stone’s struggles with drug addiction and disillusionment, Prine exposes the painful reality many soldiers faced after combat.
The song’s most haunting line— “There’s a hole in daddy’s arm where all the money goes”—is one of the most chilling lyrics in American folk music. It starkly portrays the downward spiral of addiction and the neglect veterans often experienced after returning home. Accompanied by a simple, melancholic melody, Prine’s delivery makes Sam’s tragedy feel deeply personal and heartbreakingly real.
Despite its grim subject matter, “Sam Stone” became one of Prine’s most powerful and enduring songs, shedding light on issues that were rarely discussed at the time. Its raw honesty and social commentary continue to resonate, proving that Prine was not just a songwriter but a voice for the forgotten.
3. “Paradise” (1971)
John Prine’s “Paradise” is a heartfelt, autobiographical ballad that serves as both a tribute to his parents and a lament for the destruction of the natural world. Written about the small Kentucky town of Paradise, where his family spent summers, the song tells the story of how the coal industry ravaged the once-beautiful landscape.
With lines like “Then the coal company came with the world’s largest shovel, and they tortured the timber and stripped all the land”, Prine captures both nostalgia and sorrow. The song’s simple folk melody, paired with his plaintive vocals, makes the loss of this childhood paradise feel deeply personal.
Though written in 1971, “Paradise” remains a poignant environmental anthem, warning of the dangers of greed and industrial destruction. It has been covered by numerous artists, including John Denver and The Everly Brothers, but Prine’s original version remains unmatched in its sincerity and emotional weight.
4. “Hello in There” (1971)
With “Hello in There,” John Prine crafted one of the most touching songs ever written about loneliness and aging. Released in 1971, this deeply moving ballad tells the story of elderly people who feel forgotten by the world.
Prine’s lyrics are masterful in their empathy, painting pictures of people who once lived full lives but now find themselves alone. The line “We lost Davy in the Korean War, and I still don’t know what for” subtly speaks to both personal grief and the senselessness of war. The refrain— “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”—serves as a quiet call for kindness and human connection.
The song’s gentle acoustic arrangement and Prine’s warm, reflective vocals make it even more powerful. “Hello in There” isn’t just a song—it’s a plea for compassion, making it one of the most timeless tracks in Prine’s catalog.
5. “In Spite of Ourselves” (1999)
John Prine’s “In Spite of Ourselves” is a refreshingly lighthearted love song that embraces the quirks and imperfections of relationships. Released as the title track of his 1999 duets album, the song features country-folk singer Iris DeMent, whose twangy, playful delivery perfectly complements Prine’s signature gravelly voice.
Unlike many of Prine’s more melancholic ballads, this one is filled with humor and charm, depicting a couple who may not be perfect but love each other deeply despite their flaws. Lines like “She don’t like her eggs all runny, she thinks crossin’ her legs is funny” and “He ain’t got laid in a month of Sundays, caught him once and he was sniffin’ my undies” add a level of everyday authenticity that makes the song so relatable.
The stripped-down acoustic arrangement keeps the focus on the witty lyrics and playful vocal chemistry between Prine and DeMent. “In Spite of Ourselves” is a testament to Prine’s ability to craft songs that are both deeply human and immensely entertaining, proving that love, at its core, is about embracing each other’s eccentricities.
6. “Lake Marie” (1995)
“Lake Marie” is one of John Prine’s most enigmatic and haunting songs. Released in 1995 on Lost Dogs and Mixed Blessings, the track weaves together seemingly disparate stories, creating a mesmerizing narrative that shifts between romance, history, and tragedy.
The song begins with a nostalgic tale of young love set against the backdrop of two twin lakes on the Illinois-Wisconsin border. But as the verses progress, the mood darkens, referencing historical violence and a mysterious murder. Prine’s storytelling is at its best here, balancing surreal imagery with raw emotional depth.
Musically, “Lake Marie” has a hypnotic rhythm, driven by a steady drumbeat and electric guitar licks that build tension as the song unfolds. The contrast between the bright memories of childhood and the chilling violence that later takes over the song gives it an eerie, almost cinematic quality.
One of Prine’s most experimental tracks, “Lake Marie” proves his ability to push the boundaries of folk storytelling, creating a song that lingers long after it ends.
7. “Speed of the Sound of Loneliness” (1986)
Few songs capture the weight of loneliness as effectively as “Speed of the Sound of Loneliness.” Released in 1986 on German Afternoons, this heartbreakingly beautiful track explores the emotional distance between two people who have drifted apart.
The song’s opening line— “You come home late and you come home early”—immediately sets the tone of a fractured relationship where love has faded into silence. Prine’s mournful vocals, paired with the song’s melancholic melody, make every word feel deeply personal.
The song’s title itself is a poetic way of describing how loneliness isn’t just an emotion—it moves and spreads, consuming everything in its path. Prine’s lyrics are simple yet profound, making this one of his most beloved and enduring works.
Covered by artists such as Nanci Griffith and Kim Carnes, “Speed of the Sound of Loneliness” remains one of Prine’s most devastatingly beautiful compositions, a song that resonates deeply with anyone who has ever felt lost in love.
8. “Souvenirs” (1972)
John Prine’s “Souvenirs” is a wistful ballad that perfectly captures the bittersweet nature of nostalgia. Released in 1972 on Diamonds in the Rough, the song reflects on the passage of time and the small mementos—both physical and emotional—that we carry with us from the past.
Lines like “Memories, they can’t be boughten, they can’t be won at carnivals for free” highlight Prine’s ability to turn simple truths into poetic wisdom. The song’s stripped-down acoustic arrangement enhances its intimacy, making it feel like a conversation between old friends reminiscing about days gone by.
Prine’s voice carries a quiet sadness, yet there’s also warmth in the way he sings about the memories he holds onto. “Souvenirs” is a reminder that while time moves forward, the moments that shape us never truly fade.
9. “Illegal Smile” (1971)
Kicking off his 1971 debut album, “Illegal Smile” is one of John Prine’s most humorous and clever songs. Often interpreted as a lighthearted ode to marijuana use, the song is filled with witty wordplay and a catchy folk melody that instantly puts listeners in a good mood.
Prine’s lyrics play with double meanings, making the song enjoyable whether or not you take it as a literal reference to cannabis. The chorus— “But fortunately I have the key to escape reality”—feels like an anthem for anyone who has ever needed a little break from life’s troubles.
With its playful nature and singalong quality, “Illegal Smile” became an early fan favorite, showcasing Prine’s knack for blending humor with insight. While he would go on to write deeper and more serious songs, this track remains a charming reminder of his sharp wit and easygoing spirit.
10. “Fish and Whistle” (1978)
“Fish and Whistle” is one of John Prine’s most uplifting songs, blending gospel influences with his signature folk storytelling. Released on his 1978 album Bruised Orange, the track carries themes of redemption, resilience, and learning to appreciate life’s simple moments.
The chorus— “Father forgive us for what we must do, you forgive us, we’ll forgive you”—reflects Prine’s ability to touch on deep subjects in a way that feels both profound and playful. The song is filled with whimsical imagery, like washing dishes in the morning and skipping stones, making it feel like a snapshot of everyday life.
With its upbeat tempo and singalong chorus, “Fish and Whistle” is a reminder that even in hard times, joy can be found in the little things. It’s a perfect example of Prine’s gift for writing songs that are both reflective and lighthearted, leaving listeners with a sense of hope and warmth.
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.
