<body><div><figure><img src="https://img.particlenews.com/image.php?type=thumbnail_580x000&amp;url=1c427q_0vg4EQSR00" alt="https://img.particlenews.com/image.php?url=1c427q_0vg4EQSR00" width="1000" height="563" ></figure><p>John Prine, the legendary folk singer and songwriter, left an indelible mark on the world of music with his raw and heartfelt storytelling. Known for his witty lyrics, deep sense of humanity, and ability to find beauty in everyday moments, Prine’s songs have resonated with generations of listeners. From poignant tales of love and loss to clever reflections on life’s quirks, his music has the rare power to make you laugh, cry, and think—all in the span of a single verse.</p><p>In this article, we’re diving into the top 10 most popular John Prine songs of all time. Whether you’re a lifelong fan or just discovering his catalog, these tracks showcase the breadth of his talent and the timeless appeal of his work. From the iconic “Angel from Montgomery” to the soul-stirring “Paradise,” each song on this list captures the essence of what made John Prine a true American treasure. Get ready to revisit some classics—or perhaps find a new favorite—because these songs are more than just music; they’re stories, emotions, and moments that have shaped the lives of many. Let’s celebrate the genius of John Prine through his most beloved tunes.</p><h2>1. Angel from Montgomery (1971)</h2><div style="position:relative;width:100%; height:0; padding-bottom: 56.25%;"><iframe src="https://www.youtube.com/embed/U6cagWYTGCY?feature=oembed" allowfullscreen frameborder="0" style="width:100%; height:100%;top:0; left:0; position:absolute"></iframe></div><p>“Angel from Montgomery” is one of John Prine’s most iconic songs, written from the perspective of a disillusioned woman trapped in a mundane life. Released in 1971 on his self-titled debut album, the song’s poignant lyrics and soulful melody tell the story of longing and regret. With lines like “To believe in this living is just a hard way to go,” Prine captures the heartache of unfulfilled dreams. The song has since been covered by Bonnie Raitt, adding to its enduring legacy. This timeless piece resonates with anyone who has ever felt the ache of wanting more from life.</p><h2>2. Sam Stone (1971)</h2><div style="position:relative;width:100%; height:0; padding-bottom: 56.25%;"><iframe src="https://www.youtube.com/embed/OLVWEYUqGew?feature=oembed" allowfullscreen frameborder="0" style="width:100%; height:100%;top:0; left:0; position:absolute"></iframe></div><p>Released in 1971, “Sam Stone” is a haunting ballad that tells the tragic story of a Vietnam War veteran who returns home physically and emotionally broken. With the unforgettable line “There’s a hole in daddy’s arm where all the money goes,” Prine paints a vivid picture of addiction and despair. The song’s stark portrayal of the hidden costs of war struck a nerve with listeners and became one of Prine’s most powerful anti-war statements. Its emotional depth and unflinching honesty make it one of his most enduring works.</p><h2>3. Paradise (1971)</h2><div style="position:relative;width:100%; height:0; padding-bottom: 56.25%;"><iframe src="https://www.youtube.com/embed/ediaZ5DhYjw?feature=oembed" allowfullscreen frameborder="0" style="width:100%; height:100%;top:0; left:0; position:absolute"></iframe></div><p>“Paradise,” released on Prine’s 1971 debut album, is a heartfelt ode to his parents’ hometown in Kentucky, which was devastated by coal mining. The song’s gentle, folk-based melody belies its strong environmental message, lamenting the destruction of natural beauty for corporate greed. With lines like “Mr. Peabody’s coal train has hauled it away,” Prine captures the sense of loss felt by communities affected by industrialization. “Paradise” stands as a moving tribute to the places we come from and the forces that change them.</p><h2>4. Hello in There (1971)</h2><div style="position:relative;width:100%; height:0; padding-bottom: 56.25%;"><iframe src="https://www.youtube.com/embed/OVhA01J0Zsg?feature=oembed" allowfullscreen frameborder="0" style="width:100%; height:100%;top:0; left:0; position:absolute"></iframe></div><p>“Hello in There,” also from Prine’s 1971 debut, is a tender and empathetic exploration of loneliness in old age. In a society often obsessed with youth, Prine gives voice to the elderly, reminding us all of their deep wells of experience and emotion. The song’s simple refrain, “So if you’re walking down the street sometime, and spot some hollow ancient eyes, please don’t just pass ’em by,” encourages listeners to acknowledge the humanity in everyone. Its timeless message of compassion continues to strike a chord with audiences.</p><h2>5. In Spite of Ourselves (1999)</h2><div style="position:relative;width:100%; height:0; padding-bottom: 56.25%;"><iframe src="https://www.youtube.com/embed/gA-vD5pyuS4?feature=oembed" allowfullscreen frameborder="0" style="width:100%; height:100%;top:0; left:0; position:absolute"></iframe></div><p>“In Spite of Ourselves” is a delightful duet that Prine recorded with Iris DeMent for his 1999 album of the same name. The song offers a humorous, down-to-earth look at love between two perfectly imperfect people. Prine’s witty lyrics and DeMent’s playful harmonies create a charming chemistry that makes this song a fan favorite. With its mix of humor and heart, “In Spite of Ourselves” showcases Prine’s ability to find beauty in life’s quirks, and it remains one of his most beloved songs.</p><h2>6. Lake Marie (1995)</h2><div style="position:relative;width:100%; height:0; padding-bottom: 56.25%;"><iframe src="https://www.youtube.com/embed/vzCjQwt2rgI?feature=oembed" allowfullscreen frameborder="0" style="width:100%; height:100%;top:0; left:0; position:absolute"></iframe></div><p>“Lake Marie,” released in 1995 on the Lost Dogs and Mixed Blessings album, is a mesmerizing blend of storytelling and folk-rock. Prine weaves together seemingly unrelated stories—of love, mystery, and Native American history—against the backdrop of Lake Marie. With its haunting refrain, “We were standing, standing by peaceful waters,” the song evokes a sense of nostalgia and loss. “Lake Marie” is one of Prine’s more experimental works, blending spoken word with traditional song structure, and it showcases his knack for creating vivid, cinematic narratives.</p><h2>7. Illegal Smile (1971)</h2><div style="position:relative;width:100%; height:0; padding-bottom: 56.25%;"><iframe src="https://www.youtube.com/embed/MmjnQjRvPUQ?feature=oembed" allowfullscreen frameborder="0" style="width:100%; height:100%;top:0; left:0; position:absolute"></iframe></div><p>“Illegal Smile,” from Prine’s 1971 debut album, is a lighthearted, tongue-in-cheek anthem that many interpret as a sly nod to marijuana use. However, Prine has said it’s more about finding ways to cope with life’s stresses. With its playful lyrics and infectious melody, the song became an instant favorite. Its clever wordplay and subtle rebellion capture the spirit of the counterculture era. “Illegal Smile” remains one of Prine’s most beloved songs for its humor and upbeat vibe.</p><h2>8. Souvenirs (1972)</h2><div style="position:relative;width:100%; height:0; padding-bottom: 56.25%;"><iframe src="https://www.youtube.com/embed/WMJylUzUJ8E?feature=oembed" allowfullscreen frameborder="0" style="width:100%; height:100%;top:0; left:0; position:absolute"></iframe></div><p>“Souvenirs,” released in 1972 on Diamonds in the Rough, is a bittersweet reflection on memories and the passing of time. The song’s simple yet evocative lyrics—”Broken hearts and dirty windows make life difficult to see”—speak to the way we hold onto pieces of the past, even as they fade. With its melancholic tone and acoustic arrangement, “Souvenirs” captures the feeling of nostalgia and the pain of letting go. It’s a testament to Prine’s gift for turning personal reflections into universally relatable songs.</p><h2>9. Clay Pigeons (2005)</h2><div style="position:relative;width:100%; height:0; padding-bottom: 56.25%;"><iframe src="https://www.youtube.com/embed/20Rucu7uNwc?feature=oembed" allowfullscreen frameborder="0" style="width:100%; height:100%;top:0; left:0; position:absolute"></iframe></div><p>Originally written by Blaze Foley, “Clay Pigeons” was covered by Prine on his 2005 album Fair &amp; Square. Prine’s version of this song brings an additional layer of warmth and melancholy to the story of a man trying to start his life over again. With its laid-back, country-folk vibe, “Clay Pigeons” is a meditation on taking control of your own fate, even when faced with adversity. Prine’s unique ability to convey both sadness and hope makes this cover a standout in his later catalog.</p><h2>10. Fish and Whistle (1978)</h2><div style="position:relative;width:100%; height:0; padding-bottom: 56.25%;"><iframe src="https://www.youtube.com/embed/QYxlxYSCvFg?feature=oembed" allowfullscreen frameborder="0" style="width:100%; height:100%;top:0; left:0; position:absolute"></iframe></div><p>“Fish and Whistle,” from Prine’s 1978 album Bruised Orange, is a catchy, upbeat tune that blends humor with a deeper existential undertone. The song’s lyrics reflect on human imperfection and the search for redemption, with Prine humorously noting, “Father, forgive us for what we must do.” The song’s simple, repetitive structure belies its philosophical depth, making it one of Prine’s more thought-provoking, yet lighthearted, songs. Its infectious melody and relatable themes have made it a fan favorite over the years.</p></div></body>

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10 Best John Prine Songs of All Time

John Prine, the legendary folk singer and songwriter, left an indelible mark on the world of music with his raw and heartfelt storytelling. Known for his witty lyrics, deep sense of humanity, and ability to find beauty in everyday moments, Prine’s songs have resonated with generations of listeners. From poignant tales of love and loss to clever reflections on life’s quirks, his music has the rare power to make you laugh, cry, and think—all in the span of a single verse.