When it comes to storytelling through song, few artists have left as profound a mark as John Prine. A master of blending wit, wisdom, and heartfelt emotion, Prine’s songs have resonated with generations of listeners. From his early days as a mailman penning tunes on his routes to becoming one of the most revered songwriters in American music, Prine’s catalog spans decades of timeless compositions. His ability to capture the intricacies of everyday life—be it love, loss, or the humor in between—makes his music feel like a trusted companion through the highs and lows of life.
In this article, we’ll take a journey through the top 10 most popular John Prine songs of all time, showcasing the tracks that have cemented his legacy and continue to inspire both fans and fellow musicians alike. Whether you’re a longtime Prine devotee or just discovering his genius, these songs offer a glimpse into the heart and soul of an artist who could turn simple melodies into profound statements on the human condition. So, sit back, turn up the volume, and let’s dive into the unforgettable world of John Prine’s most beloved songs.
1. “Angel from Montgomery” (1971)
Released on John Prine’s self-titled debut album in 1971, “Angel from Montgomery” became one of his most enduring and beloved songs. In this hauntingly beautiful track, Prine paints a poignant picture of a woman stuck in a lifeless marriage, longing for a sense of purpose and escape. The lyrics are raw, capturing a deep emotional yearning for change and the hope that something more meaningful might come her way. The narrator’s longing for someone—an angel of sorts—to deliver her from her dull, painful existence resonated deeply with listeners, offering a snapshot of the internal struggles many people face in their everyday lives.
Prine’s ability to give voice to a middle-aged woman’s perspective with such empathy and grace is part of what makes this song so timeless. He taps into universal themes of frustration, hope, and the human desire for redemption, making “Angel from Montgomery” relatable across generations. The song’s simple yet effective imagery—like the desire to be freed from the “broken wings of an angel”—creates a vivid portrait of this woman’s internal world. Though the song tells a deeply personal story, its themes of escape, longing, and searching for something greater transcend its narrative, capturing a broader sense of human vulnerability.
The song was later covered by Bonnie Raitt in 1974, and her version helped introduce the song to a wider audience, cementing its place as a classic. With its sparse instrumentation and Prine’s aching, soulful delivery, “Angel from Montgomery” continues to be one of his most recognized and cherished songs, a testament to his extraordinary songwriting talent and his ability to connect with listeners on a deeply emotional level.
2. “Sam Stone” (1971)
“Sam Stone” is another unforgettable track from Prine’s groundbreaking 1971 debut album, and it’s one of the most emotionally powerful and raw songs in his catalog. The narrative is a harrowing look into the life of a Vietnam War veteran named Sam Stone, who returns home physically and emotionally scarred from the war. Struggling to cope with the trauma, he turns to heroin to numb his pain, falling deeper into addiction. The image of the “hole in daddy’s arm where all the money goes” became one of Prine’s most iconic and chilling lines, powerfully underscoring the devastating impact of war and addiction on both the individual and the family.
The song is deeply political, shedding light on the struggles of veterans returning from Vietnam, a topic that was largely overlooked in popular music at the time. Through Sam’s story, Prine offers a heartbreaking look at the emotional toll war takes, not just on soldiers, but also on the families and communities that have to deal with the fallout. The slow, mournful rhythm of the song, paired with Prine’s tender yet sorrowful delivery, creates a somber atmosphere that pulls the listener into Sam’s world of pain and helplessness.
“Sam Stone” isn’t just about one man’s personal battle—it’s a commentary on the broader social and political issues facing America during the post-Vietnam War era. By personalizing these struggles through Sam’s story, Prine was able to humanize the complexities of addiction, war, and the broken promises to those who served their country. The song’s tragic but necessary reflection on the consequences of war has made it one of Prine’s most powerful and poignant songs, remaining relevant and deeply moving decades after its release.
3. “Hello in There” (1971)
“Hello in There,” also from Prine’s 1971 debut album, is a deeply moving song that captures the loneliness and isolation of aging. The song focuses on the lives of elderly individuals who are often forgotten or overlooked by society, highlighting how many people in their later years live in silence, disconnected from the world around them. Prine’s lyrics are a tender plea for compassion and human connection, reminding us that even as we grow older, we still have a need for love and attention.
The song’s narrative is told through the perspective of a man observing the lives of aging neighbors, including an elderly woman and a man whose once-vibrant life is now reduced to waiting for the inevitable. With lines like “Is there anyone who will listen to me?” Prine perfectly captures the feelings of invisibility that many older people experience as they grow isolated from their communities. The repeating refrain “Hello in there, hello” acts as both a literal and metaphorical call for human connection—a simple yet powerful reminder that reaching out can make a profound difference in someone’s life.
Prine’s delicate yet expressive delivery, coupled with the song’s gentle, folk-inspired melody, evokes a sense of deep empathy for those who live in quiet despair. “Hello in There” is a reflection on how the passage of time affects both individuals and society, and it serves as a poignant reminder to connect with those who may feel forgotten. The song’s understated beauty and profound message make it one of Prine’s most beloved tracks, touching listeners in a way that few songs can.
4. “Paradise” (1971)
“Paradise,” featured on Prine’s debut album in 1971, is a nostalgic and deeply personal reflection on the small Kentucky town where Prine’s family roots lie. The song paints a vivid picture of a place that was once lush and vibrant, teeming with life and natural beauty, but which has been devastated by the destructive forces of strip mining. Through his poignant lyrics, Prine mourns the loss of the land that once held the memories of his childhood, reflecting on how industrial progress has ravaged the places that were once central to his sense of home.
The lyrics of “Paradise” are both sorrowful and reflective, evoking a sense of longing for a time when things seemed simpler and more innocent. “Paradise” is not only an elegy for a place that no longer exists but also a commentary on the broader environmental devastation caused by unchecked industrialization. The image of “the coal company’s dirty hands” is a powerful indictment of the way businesses can exploit the land, leaving destruction in their wake. At the same time, the song is filled with an aching sense of nostalgia, recalling a time when the town of Paradise was a peaceful and happy place, full of life and love.
Prine’s ability to intertwine personal history with universal themes of loss and environmental destruction is a testament to his skill as a songwriter. The song resonates not only with people from Kentucky, but with anyone who has watched a cherished place change or disappear due to industrial development. “Paradise” remains a timeless anthem for anyone who has felt the sting of progress that comes at the expense of nature and personal history. With its simple, yet powerful melody, the song continues to evoke strong emotions from listeners, serving as a haunting reminder of what has been lost.
5. “In Spite of Ourselves” (1999)
“In Spite of Ourselves,” released in 1999, is a playful and delightful duet between John Prine and Iris DeMent. The song is a humorous yet tender celebration of love in all its messy, imperfect glory. The lyrics portray a couple who are far from perfect, yet their flaws and quirks are part of what makes their relationship special. Through its tongue-in-cheek lyrics, the song explores how love isn’t about perfection but about accepting one another’s flaws, learning to live with them, and appreciating the imperfect moments that come together to form something real.
The chemistry between Prine and DeMent is palpable, with their voices blending effortlessly throughout the song. Their playful banter and humor infuse the song with a lighthearted energy that makes it a joy to listen to. Lines like “You’re the reason I’m laughing and crying, and I’m sighing, and I’m loving you,” capture the contradictory emotions that make love so complicated and beautiful. The song’s folksy instrumentation, with its upbeat rhythm and catchy melody, further amplifies the joy and warmth that radiates from the lyrics.
Prine’s ability to capture the complexities of love with such humor and sincerity is on full display in “In Spite of Ourselves.” The song reminds listeners that love isn’t always easy, but it’s the imperfections and the willingness to stick together despite them that make it worth it. As lighthearted as the song feels, it is also deeply sincere, showing that Prine understood love’s messy, unpredictable nature better than most. The song has become a fan favorite, resonating with anyone who has ever experienced love’s delightful absurdities. It’s a song that makes you laugh, smile, and feel deeply connected to the human experience of loving and being loved.
6. “Lake Marie” (1995)
“Lake Marie,” from Prine’s 1995 album Lost Dogs and Mixed Blessings, stands out as one of his most enigmatic and complex songs. At first listen, it feels like a simple narrative, yet its layered structure reveals a deeper, more intricate tale. The song weaves together various characters and stories, including a murder mystery, a love story, and reflections on the passage of time. The song’s unusual structure, shifting between different voices and storylines, keeps listeners engaged and guessing as they try to piece together the narrative’s many threads.
The song’s title, “Lake Marie,” refers to a location that serves as the backdrop for the events unfolding in the song, but it also takes on a symbolic significance as a place of both beauty and tragedy. The setting evokes an eerie sense of mystery, particularly in the refrain, “We were standing / Standing by peaceful waters,” which contrasts the calmness of nature with the dark, troubling events that are being recounted. This duality—of peace and violence, love and loss—permeates the entire song, giving it a haunting yet poetic quality that sticks with the listener long after the music fades.
Prine’s lyrics are a masterful blend of the personal and the universal, using a local legend to explore themes of time, memory, and the consequences of our actions. The murder mystery element, though central to the song, is never fully explained, leaving much to the listener’s imagination. Yet it’s clear that the story isn’t just about the crime itself but about how it intersects with the broader passage of life. In “Lake Marie,” Prine captures a sense of place and history while inviting the listener to reflect on the cycles of love, loss, and redemption that shape us all. This song’s haunting beauty and complex storytelling make it one of Prine’s most compelling and unforgettable works.
7. “Illegal Smile” (1971)
“Illegal Smile,” from Prine’s 1971 debut album, is a playful yet subtly subversive song that invites listeners to embrace life’s absurdities. The song’s catchy melody and lighthearted delivery belie the deeper message underneath: sometimes we all need a way to escape from the weight of the world, even if that escape is just for a little while. Though the song never directly mentions marijuana, its references to seeking relief through an “illegal smile” have often been interpreted as a wink toward drug use. But the song is more than just a cheeky nod to counterculture; it’s also about finding moments of joy in the midst of hardship.
With its upbeat, folksy rhythm and Prine’s signature dry humor, “Illegal Smile” conveys a sense of release from the pressures of everyday life. The song’s carefree tone and clever wordplay make it instantly infectious, inviting listeners to sing along and smile despite the difficulties that may come their way. Lines like “I woke up this morning / And I got myself a beer” reflect the simple yet powerful ways people find comfort in the face of life’s challenges, whether through substances or other forms of relief. Prine’s laid-back delivery adds to the song’s charm, turning a serious theme into something lighthearted and fun.
At its core, “Illegal Smile” is a celebration of the small, rebellious acts that help us cope with life’s frustrations. It’s a reminder that, even in tough times, there’s always room for a little humor and self-care. With its catchy melody and easygoing vibe, the song became a fan favorite and remains one of Prine’s most beloved tracks. By wrapping up its deeper themes in a humorous, catchy package, “Illegal Smile” shows Prine’s knack for blending wit with meaning, making it both a fun tune and a thoughtful commentary on the human need for escape and relief.
8. “Clay Pigeons” (2005)
Although “Clay Pigeons” was originally written by Blaze Foley, John Prine’s 2005 rendition brought new depth and meaning to this beautiful, reflective song. The song captures the feeling of starting over, finding solace in life’s quieter moments, and seeking peace amidst the chaos. Prine’s version of the song is tender and thoughtful, with his signature voice bringing a warmth and vulnerability to Foley’s lyrics. Through his careful interpretation, Prine made the song his own, infusing it with a sense of both melancholy and hope.
The lyrics of “Clay Pigeons” evoke the feeling of being adrift, trying to find one’s way after hardship or loss. The imagery of shooting clay pigeons in a vast, open field is symbolic of feeling like an outsider, someone disconnected from the world around them. Yet, there’s also a sense of redemption and peace in the act, as if by embracing the isolation, one might eventually find clarity and a new purpose. The song’s gentle acoustic arrangement and Prine’s soft, soothing delivery create a serene atmosphere, drawing listeners into the reflective mood of the song.
In Prine’s version, the theme of finding solace in nature and the simplicity of life resonates strongly. It’s a song about moving forward, finding peace, and letting go of the past. Through his heartfelt performance, Prine shows how even the simplest moments—whether it’s sitting by the river or contemplating life’s uncertainties—can lead to moments of insight and healing. “Clay Pigeons” may not have been written by Prine, but his interpretation of the song gives it a new layer of emotional depth, making it a standout track in his later catalog.
9. “That’s the Way the World Goes ‘Round” (1978)
Released in 1978 on Prine’s Bruised Orange album, “That’s the Way the World Goes ’Round” is a lighthearted yet poignant reflection on life’s unpredictability. With its playful rhythm and catchy melody, the song tells the story of a man who experiences a series of misfortunes—losing his job, being betrayed, dealing with disappointment—but who accepts these setbacks with a sense of humor and resilience. The repeated refrain “That’s the way that the world goes ’round” serves as a reminder not to take life too seriously and to roll with the punches when things don’t go as planned.
The song is full of Prine’s signature wit, using humor to soften the blow of life’s hard knocks. The line “I know I’m gonna miss her / When I get home” is both humorous and relatable, capturing the way life often throws curveballs when we least expect it. The song’s upbeat tempo and infectious chorus make it an instant sing-along anthem, but beneath the surface, it’s a song about accepting the unpredictable nature of life. Life is full of ups and downs, and sometimes the best thing we can do is laugh at the absurdity of it all and keep moving forward.
“That’s the Way the World Goes ’Round” became a fan favorite thanks to its joyful, carefree vibe, and it remains one of Prine’s most enduring tracks. The song’s message—that life goes on regardless of our setbacks—resonates with anyone who has experienced the highs and lows of existence. With its humor and optimism, the song serves as a gentle reminder that, no matter what happens, the world keeps turning, and we have to keep going with it.
10. “When I Get to Heaven” (2018)
“When I Get to Heaven,” from Prine’s 2018 album The Tree of Forgiveness, is a joyful and whimsical reflection on life, death, and the afterlife. In this song, Prine imagines all the things he’ll do when he reaches heaven, from smoking a cigarette nine miles long to catching up with long-lost friends and family members. His signature mix of humor and heart shines through in this lighthearted tune, which is both a farewell and a celebration of life.
The song’s playful tone is balanced by moments of deep reflection, as Prine imagines what heaven will be like and how he will reconcile with the world once he’s gone. The line “I’m gonna get a tattoo of an angel on my arm / And I’ll go out in the yard and try to catch a fish,” reflects the song’s irreverent humor while also conveying a sense of peace and acceptance. Prine’s ability to tackle the subject of mortality with a smile is one of the reasons this song resonated so deeply with fans, especially as it marked one of his final musical statements before his passing in 2020.
As a song that imagines the afterlife in such a whimsical way, “When I Get to Heaven” serves as a joyful reminder to live life fully and embrace its absurdities. It’s a song about celebrating the moments we have, finding humor in the inevitable, and cherishing our time on earth. The track is a fitting conclusion to Prine’s remarkable career, leaving listeners with a sense of warmth and lightness, as if he were saying goodbye with a smile. It’s a perfect reflection of his legacy—an artist who faced life’s challenges with humor, grace, and a generous heart.
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.
