Few songwriters have managed to capture the raw essence of life quite like John Prine. With a voice as humble as his lyrics, Prine’s blend of wit, heartbreak, and wisdom has left a mark on generations of music lovers. From his early days as a Chicago mailman playing open mics, to becoming a celebrated voice in the pantheon of American folk and country music, Prine’s songs resonate with an authenticity that never fades. His storytelling is unparalleled, weaving tales of love, loss, humor, and humanity with a deft touch that feels both personal and universal.
Whether you’re a long-time fan or just discovering his work, John Prine’s music has something for everyone. His most beloved tracks showcase the depth of his songwriting, taking listeners on a journey through poignant ballads and tongue-in-cheek satire, often within the same breath. In this article, we’re counting down the top 10 most popular John Prine songs of all time—those timeless tunes that have cemented his legacy as one of the greatest songwriters in history. From heart-wrenching classics to fan-favorite gems, these songs are a testament to Prine’s unique ability to find beauty in the ordinary and meaning in every note.
1. Angel from Montgomery (1971)
Released in 1971 on his self-titled debut album, “Angel from Montgomery” has become one of John Prine’s most iconic and enduring songs. Written from the perspective of a middle-aged woman feeling trapped in a loveless marriage, the track masterfully encapsulates the loneliness and yearning for a better life. With lyrics like, “Make me an angel that flies from Montgomery,” Prine evokes a deep sense of longing and hope that resonates with listeners. His remarkable ability to embody his characters infuses the song with empathy and authenticity, allowing audiences to connect with the woman’s plight. Bonnie Raitt’s celebrated cover of the song introduced it to an even wider audience, adding to its acclaim. However, it remains a defining track for Prine, showcasing his talent for storytelling through music. The melody is simple yet haunting, and it perfectly complements the poignant lyrics, which explore themes of unfulfilled dreams and the search for redemption. This timeless classic continues to be a favorite among both fans and performers, reflecting the universal human desire for escape and liberation. Prine’s “Angel from Montgomery” not only tells a compelling story but also captures the emotional essence of longing that many can relate to, ensuring its place in the hearts of listeners for generations.
2. Hello in There (1971)
“Hello in There,” another poignant track from John Prine’s debut album released in 1971, is a haunting exploration of loneliness and the passage of time. The song tells the story of elderly individuals who feel forgotten and isolated in a rapidly changing world. With evocative lines such as, “Old trees just grow stronger, and old rivers grow wilder every day,” Prine’s lyrics paint a vivid picture of aging and the silent struggles that accompany it. His compassionate storytelling shines through, giving voice to those often overlooked by society. The slow, mournful melody creates an atmosphere of reflection, inviting listeners to consider the lives and experiences of others. Prine’s ability to convey complex emotions with simplicity is evident here; he captures the essence of human connection and the desire for recognition and understanding. As he gently urges listeners to acknowledge the elderly, the song becomes a powerful reminder of the importance of compassion and empathy in our interactions. “Hello in There” resonates deeply with anyone who has felt the weight of time and isolation, reminding us all of the quiet dignity that accompanies growing old. Prine’s masterful lyricism and poignant delivery make this song an enduring classic that remains relevant to this day.
3. Paradise (1971)
“Paradise,” released in 1971, is a nostalgic tribute to John Prine’s childhood memories of visiting his family’s hometown in Kentucky, a place devastated by the coal mining industry. The song paints a vivid picture of the Green River and the once-thriving town of Paradise, which has now vanished due to environmental destruction. Prine’s storytelling is deeply personal, intertwining themes of loss and memory with a broader environmental message. Lines that evoke the beauty of the land contrast sharply with the harsh reality of its destruction, showcasing Prine’s talent for blending personal experience with social commentary. The catchy, folk-driven melody invites listeners to sing along, even as the lyrics grapple with sadness and nostalgia. It serves as a heartfelt reminder of the natural beauty that once existed and the consequences of human intervention. This duality—of joy and sorrow—makes “Paradise” one of Prine’s most beloved songs. The track’s ability to resonate with both personal and collective experiences reflects the universal theme of longing for a lost home. In capturing the essence of a place and its people, “Paradise” stands as a timeless testament to Prine’s profound songwriting and his deep connection to the environment and community.
4. Sam Stone (1971)
“Sam Stone,” released in 1971, is one of John Prine’s most heartbreaking songs, tackling the heavy subject of a war veteran returning home with both physical and emotional scars. The narrative centers on a soldier who struggles with addiction after experiencing the trauma of war, captured in the haunting line, “There’s a hole in Daddy’s arm where all the money goes.” This stark imagery conveys the devastating impact of drug addiction, making it an unforgettable anti-war anthem in the post-Vietnam era. Prine’s blunt lyricism, paired with a mournful melody, effectively evokes the pain and disillusionment faced by veterans and their families. The song’s raw honesty speaks to the broader societal issues surrounding war, mental health, and the struggles that many service members encounter upon returning home. Prine’s ability to humanize these experiences through storytelling resonates deeply with listeners, creating a powerful emotional connection. “Sam Stone” is a poignant reminder of the sacrifices made by those who serve, and its legacy continues to impact audiences today. This deeply affecting song showcases Prine’s talent for weaving complex social issues into personal narratives, ensuring its place as a significant piece in his discography.
5. Illegal Smile (1971)
“Illegal Smile,” released in 1971, is a playful and lighthearted anthem that many interpret as a nod to the joys of marijuana use. With its infectious melody and witty lyrics, the song captures the essence of carefree living and finding happiness in the little things. John Prine’s clever wordplay and laid-back delivery invite listeners to join in on the fun, making it one of the most enjoyable tracks on his debut album. Although Prine himself claimed the song wasn’t exclusively about smoking weed, its double meanings and humorous undertones have endeared it to fans over the years. Lines that express a carefree spirit resonate with listeners looking for an escape from the pressures of everyday life. The upbeat vibe and catchy chorus create an atmosphere of joy and lightness, encouraging everyone to embrace their own version of happiness. “Illegal Smile” ultimately celebrates the small pleasures that can brighten our days, whether they come from simple moments or shared laughter. This classic Prine track continues to evoke smiles and laughter, reminding us of the importance of joy and levity in our lives. It stands as a testament to Prine’s ability to craft songs that blend humor with meaningful reflection.
6. In Spite of Ourselves (1999)
“In Spite of Ourselves” stands out as one of John Prine’s most charming and humorous duets, featuring the wonderful talents of country singer Iris DeMent. Released in 1999 on the album of the same name, the song hilariously captures the quirks and imperfections of love. Through lines like, “He ain’t got laid in a month of Sundays” and “She thinks all my jokes are corny,” the lyrics highlight the messiness and authenticity of real relationships. Prine’s signature wit, combined with DeMent’s twangy vocal delivery, creates an infectious chemistry that resonates with couples everywhere. The playful banter and relatable observations about love make the song a celebration of the ups and downs that come with any partnership. The duet format allows both artists to shine, blending their unique voices into a harmonious and delightful performance. With its catchy melody and lighthearted tone, “In Spite of Ourselves” becomes an anthem for those who understand that love is not always perfect but is always worth celebrating. This song’s humor and authenticity capture the essence of relationships, making it a favorite for fans and a cherished addition to Prine’s remarkable body of work.
7. Clay Pigeons (2005)
Although John Prine didn’t originally write “Clay Pigeons,” his 2005 cover of Blaze Foley’s poignant track introduced it to a wider audience. Featured on Prine’s album Fair & Square, his gentle, gravelly voice brings a new depth to the tale of a man seeking solace and redemption. The song captures a bittersweet tone, exploring themes of wandering, loss, and the hope of starting anew. Prine’s interpretation adds layers of emotion, allowing listeners to connect with the character’s struggle for meaning in life. The simple acoustic arrangement complements Prine’s style, making the narrative feel intimate and relatable. As he sings about the complexities of existence, there’s a sense of vulnerability that resonates throughout the track. This song stands as a testament to Prine’s remarkable ability to take another songwriter’s work and infuse it with his own unique essence. His rendition of “Clay Pigeons” emphasizes the themes of yearning and introspection, creating an emotional landscape that invites listeners to reflect on their own journeys. Through Prine’s heartfelt delivery, this cover not only honors Foley’s original vision but also showcases Prine’s enduring talent as an interpreter of profound and relatable stories.
8. Lake Marie (1995)
“Lake Marie,” released in 1995 on Prine’s album Lost Dogs and Mixed Blessings, is a masterful composition that weaves together multiple stories, merging love, mystery, and violence against the backdrop of Lake Marie. The song’s unconventional structure captivates listeners, alternating between spoken word verses and melodic choruses, keeping them engaged throughout. Prine’s storytelling is both vivid and layered, as he recounts personal anecdotes and historical events, all tied together by the haunting refrain, “We were standing, standing by peaceful waters.” This song is not just a narrative but an exploration of complex emotions and human experiences, creating a rich tapestry that resonates with audiences. The way Prine interlaces various narratives speaks to his talent for crafting compelling and intricate tales. With its atmospheric soundscape and poignant lyrics, “Lake Marie” remains one of Prine’s most intriguing and enigmatic songs. Each listen reveals new layers of meaning, making it a piece that invites deep reflection. As he delves into themes of love and loss, Prine’s distinctive voice and thoughtful storytelling create an unforgettable experience for anyone willing to journey into the heart of this remarkable song.
9. Souvenirs (1972)
Released on Diamonds in the Rough in 1972, “Souvenirs” is a bittersweet reflection on the passage of time and the memories we accumulate throughout our lives. The song’s simple, acoustic arrangement allows John Prine’s melancholy lyrics to shine, with poignant lines like, “Memories, they can’t be boughten, they can’t be won at carnivals for free.” These words encapsulate the essence of nostalgia, emphasizing the intangible nature of our experiences and the sentimental value they hold. Prine’s ability to convey complex emotions with such clarity is a hallmark of his songwriting. The wistful tone and gentle melody create an atmosphere that resonates deeply with anyone who has ever felt the ache of remembering the past. As listeners traverse the memories recounted in the song, they are reminded of their own souvenirs—those moments and experiences that shape who we are. “Souvenirs” is a perfect example of Prine’s talent for capturing the intricacies of human emotion with just a few well-chosen words. This deeply emotional track serves as a timeless reminder of the beauty and fragility of memory, ensuring its lasting impact on audiences who connect with its themes of reflection and nostalgia.
10. That’s the Way That the World Goes ‘Round (1978)
Released in 1978 on Prine’s album Bruised Orange, “That’s the Way That the World Goes ‘Round” offers a humorous yet insightful look at life’s unpredictable nature. With its bouncy, upbeat melody, the song contrasts with its sometimes dark and tongue-in-cheek lyrics, such as, “It’s a half an inch of water and you think you’re gonna drown.” Prine’s sense of humor shines through in this track, reminding us that life is filled with absurdities and unexpected challenges. The song serves as a lighthearted commentary on the ups and downs that everyone experiences, encouraging listeners to find joy even in the face of adversity. Prine’s clever observations about the human condition resonate with audiences, making it a relatable anthem for anyone who has ever faced the unexpected twists of life. The infectious melody and playful lyrics create an atmosphere of joy and laughter, inviting listeners to join in and sing along. “That’s the Way That the World Goes ‘Round” is more than just a catchy tune; it’s a reminder to embrace life’s uncertainties with humor and grace. This delightful song continues to bring smiles and laughter, proving that John Prine’s ability to find light in the darkness is as relevant today as it ever was.
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.
