John Prine, a true master of storytelling, left an indelible mark on the world of music with his heartfelt lyrics, unforgettable melodies, and the raw authenticity of his voice. Known as one of the most gifted singer-songwriters of his generation, Prine’s music resonates deeply with fans, capturing the beauty, pain, and humor of life’s most intimate moments. From small-town tales to poignant reflections on love and loss, his songs have a way of making you feel like he’s singing directly to your soul.
In this article, we take a journey through the top 10 most popular John Prine songs of all time. These tracks are more than just music; they are windows into the human experience, filled with wit, wisdom, and a touch of mischief. Whether you’re a lifelong fan or a newcomer to Prine’s genius, these songs will remind you why his legacy continues to grow, even after his passing. Get ready to laugh, cry, and hum along as we celebrate the timeless artistry of one of music’s most cherished voices. So, grab your headphones, settle in, and let the magic of John Prine take you away.
1. Angel from Montgomery (1971)
“Angel from Montgomery” is one of John Prine’s most beloved and enduring songs, a masterpiece of storytelling that captures the quiet desperation of a woman trapped in a stagnant life. First released on Prine’s 1971 self-titled debut album, the song tells the story of a middle-aged housewife longing for escape from her mundane reality. With lines like “Just give me one thing that I can hold on to,” Prine distills a lifetime of longing into a single, aching plea for something more.
The song’s brilliance lies in Prine’s ability to write from a female perspective with such authenticity and emotional depth. Inspired by a photo he saw of an elderly woman, Prine imagined what her life might have been like, crafting lyrics that feel universal in their sadness and yearning. The imagery—faded youth, a dull routine, and a distant, indifferent husband—paints a picture that resonates deeply with anyone who has ever felt stuck in their circumstances.
Though Prine’s version is revered, “Angel from Montgomery” gained widespread recognition through Bonnie Raitt’s stunning 1974 rendition. Over the years, artists like Susan Tedeschi and Carly Simon have also covered the song, further cementing its place in the American folk and country canon. Its haunting melody and poetic lyrics make it one of Prine’s defining works, a song that lingers in the heart long after it ends.
2. Hello in There (1971)
“Hello in There” is a deeply moving meditation on aging, loneliness, and the passage of time. Featured on Prine’s groundbreaking 1971 debut album, the song tells the story of an elderly couple whose children have moved away, leaving them in isolation with only memories to keep them company. Through simple yet profound lyrics, Prine urges listeners to acknowledge and reach out to the elderly, reminding us that they, too, have stories, dreams, and emotions that often go unnoticed.
From the very first lines—”We had an apartment in the city / Me and Loretta liked living there”—Prine sets a poignant scene of a once-vibrant life that has now faded into solitude. The chorus, “So if you’re walking down the street sometime / And spot some hollow ancient eyes / Please don’t just pass them by and stare / As if you didn’t care, say ‘Hello in there, hello,’” delivers an emotional punch that resonates across generations.
The song’s delicate melody and heartfelt delivery make it one of Prine’s most enduring works, often covered by artists such as Joan Baez and Bette Midler. “Hello in There” is more than just a song—it’s a call for compassion, a reminder that small acts of kindness can bridge the gap between loneliness and connection. Few songwriters can capture human emotion as effortlessly as Prine, and this song remains one of his most touching and timeless compositions.
3. Sam Stone (1971)
“Sam Stone” is one of John Prine’s most powerful and gut-wrenching songs, telling the tragic story of a Vietnam War veteran who returns home only to succumb to addiction and despair. With unflinching honesty, Prine paints a harrowing portrait of a soldier unable to reintegrate into civilian life, haunted by the trauma of war and numbing his pain with heroin.
The song’s devastating refrain, “There’s a hole in daddy’s arm where all the money goes,” is one of the most haunting lines in American folk music. It encapsulates the helplessness of addiction and the collateral damage it inflicts on families. Unlike many war protest songs of the era, “Sam Stone” doesn’t deal in broad political statements—it’s an intimate, deeply personal narrative that humanizes the cost of war in a way statistics never could.
Musically, the song’s gentle, almost lullaby-like melody contrasts starkly with its bleak subject matter, making its message even more unsettling. The combination of sorrowful storytelling and an understated arrangement ensures that “Sam Stone” lingers long after the last note fades. Decades after its release, it remains a heartbreaking anthem for veterans struggling with PTSD, addiction, and the neglect of a society that often forgets them.
4. Paradise (1971)
“Paradise” is a beautifully nostalgic yet bittersweet song that serves as both a personal reflection and an environmental lament. Written about Prine’s childhood visits to Muhlenberg County, Kentucky, the song mourns the destruction of the town’s natural beauty at the hands of the Peabody Coal Company.
Through vivid storytelling, Prine contrasts the idyllic memories of fishing and playing in the Green River with the stark reality of strip mining that eventually devastated the landscape. The chorus, “Daddy, won’t you take me back to Muhlenberg County / Down by the Green River where paradise lay?” carries a deep sense of longing, only to be answered by the heartbreaking response, “Well, I’m sorry, my son, but you’re too late in asking / Mr. Peabody’s coal train has hauled it away.”
Despite its somber theme, “Paradise” became one of Prine’s most celebrated songs, often covered by bluegrass and country artists, including Johnny Cash, John Denver, and Dwight Yoakam. Its simple chord progression and sing-along quality have made it a favorite at folk gatherings, while its environmental message remains just as relevant today.
5. Illegal Smile (1971)
Kicking off John Prine’s debut album with a playful spirit, “Illegal Smile” is often mistaken for a straightforward ode to marijuana. While Prine never denied that interpretation, he maintained that the song was more about finding happiness in life’s small, unexpected moments.
From the opening line—“When I woke up this morning, things were looking bad”—Prine sets up an everyday struggle, but instead of succumbing to negativity, he leans into humor and resilience. The catchy melody and quirky lyrics, including the memorable line “A bowl of oatmeal tried to stare me down and won,” make it clear that Prine was already a master of blending wit with heartfelt storytelling.
“I just meant it as a smile that comes to your face for no particular reason,” Prine once explained. Regardless of how listeners interpret it, “Illegal Smile” remains a fun and infectious anthem that showcases Prine’s knack for clever wordplay and his ability to infuse even the simplest moments with meaning.
6. In Spite of Ourselves (1999)
“In Spite of Ourselves” is a hilarious and heartwarming duet that perfectly captures John Prine’s signature blend of humor, charm, and sincerity. Released on his 1999 album of the same name, the song features folk and country singer Iris DeMent, whose distinctive twang adds to the song’s playful, down-to-earth vibe.
Unlike many love songs that idealize romance, “In Spite of Ourselves” revels in the quirks and imperfections of a long-term relationship. The lyrics paint a vivid picture of a couple who may not be perfect but are absolutely perfect for each other. Lines like “She thinks all my jokes are corny / Convict movies make her horny” showcase Prine’s knack for writing lyrics that are both comically blunt and deeply affectionate.
Despite its lighthearted nature, the song carries a deeper message—true love isn’t about perfection; it’s about acceptance. The chemistry between Prine and DeMent is palpable, making the song feel like an intimate conversation between two people who have been through everything together and still choose each other. The playful back-and-forth, combined with the song’s bouncy, classic country melody, has made “In Spite of Ourselves” a fan favorite and a staple at weddings and anniversaries.
7. Souvenirs (1972)
“Souvenirs” is one of John Prine’s most poignant reflections on time, memory, and the bittersweet nature of nostalgia. Originally released on his 1972 album Diamonds in the Rough, the song finds Prine looking back on the past with a mixture of longing and resignation.
From the very first line—”All the snow has turned to water”—Prine sets the stage for a song about the passage of time and the fleeting nature of life. The lyrics explore the way we hold onto mementos and memories, even as they lose their clarity over time. The chorus, “Broken hearts and dirty windows / Make life difficult to see,” is one of Prine’s most poetic and profound lines, encapsulating the way our past experiences shape our perspective on the present.
Musically, “Souvenirs” is beautifully understated, with gentle acoustic guitar and Prine’s warm, wistful vocals carrying the song’s emotional weight. Though it’s a deeply personal song, its themes resonate universally—everyone has their own set of “souvenirs” from their past, reminders of people, places, and moments that shaped them. Over the years, “Souvenirs” has remained a fan favorite, a testament to Prine’s ability to turn simple reflections into timeless art.
8. Lake Marie (1995)
“Lake Marie” is one of John Prine’s most enigmatic and haunting songs, blending love, loss, and mystery into a mesmerizing narrative. Released on his 1995 album Lost Dogs and Mixed Blessings, the song is unlike anything else in Prine’s catalog, with its hypnotic rhythm and cinematic storytelling.
The song weaves together multiple storylines, all centered around the real-life Lake Marie in Wisconsin. The first verse describes the lake’s origins, blending historical fact with Prine’s poetic imagination. The song then shifts to a deeply personal memory of a troubled romance—“Many years ago, we were an innocent young couple / Me and my cousin, Billy, we were just gettin’ started”—before taking an unexpected turn into a chilling murder scene.
The chorus—“We were standing, standing by peaceful waters”—acts almost like a haunting refrain, repeated throughout the song as if trying to make sense of the events unfolding. The way Prine juxtaposes idyllic imagery with dark themes gives the song an eerie, dreamlike quality.
“Lake Marie” has been praised for its unique storytelling approach, with many fans and critics calling it one of Prine’s finest late-career compositions. Its blend of folk, rock, and spoken-word storytelling makes it one of his most intriguing and unforgettable songs.
9. Fish and Whistle (1978)
“Fish and Whistle” is a bright and optimistic song that showcases John Prine’s ability to find joy and humor in life’s ups and downs. Released on his 1978 album Bruised Orange, the song is filled with whimsical imagery and a message of resilience, making it one of the most uplifting tracks in his catalog.
At first listen, the song’s lyrics seem playful and almost nonsensical—“Father, forgive us for what we must do / You forgive us, we’ll forgive you” —but underneath the surface, Prine is delivering a wry commentary on the human experience. The song’s recurring theme of redemption and perseverance is woven into its upbeat melody, giving it an almost gospel-like feel.
The chorus—”And we’ll whistle and go fishing in heaven”—captures the essence of Prine’s worldview: no matter what hardships come our way, there’s always something to look forward to. The song’s simple instrumentation, featuring acoustic guitar and a steady, toe-tapping rhythm, adds to its feel-good nature.
“Fish and Whistle” has become a fan favorite at concerts, often encouraging audiences to sing along. Its message of forgiveness, acceptance, and moving forward with a light heart is quintessential Prine—wise, funny, and deeply human.
10. Clay Pigeons (2005)
“Clay Pigeons” is a stunning example of John Prine’s ability to take another songwriter’s work and make it completely his own. Originally written by Blaze Foley, the song was reimagined by Prine on his 2005 album Fair & Square, bringing a warmth and intimacy that resonated deeply with his fans.
The song tells the story of a man trying to escape his past and start over, drifting through life with a mixture of hope and resignation. Lines like “I’m goin’ down to the Greyhound station, gonna get a ticket to ride” evoke a sense of aimless wandering, while the gentle acoustic melody gives the song a meditative, almost lullaby-like feel.
Prine’s version of “Clay Pigeons” feels deeply personal, as if he’s lived every word of the song himself. His gravelly, world-weary voice adds an extra layer of authenticity, making the song feel like a quiet confession between old friends.
Over the years, Prine’s rendition of “Clay Pigeons” has introduced many new listeners to Blaze Foley’s work while also becoming a staple in Prine’s own catalog. It’s a song about longing, reinvention, and the quiet beauty of everyday life—timeless themes that Prine always had a way of bringing to life in the most genuine and touching way.
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.
