John Prine’s music is the very definition of timeless. With a career spanning over five decades, his heartfelt, witty, and often poignant lyrics have earned him a revered place in the pantheon of American music. Whether you first discovered his songs in the 1970s or found them through modern covers and tributes, Prine’s ability to blend folk, country, and Americana with a unique storytelling charm has touched millions. From tender ballads to biting social commentary, his songs resonate with a universality that few songwriters can match.
In this article, we celebrate the best of John Prine’s catalog, counting down his 10 most popular songs of all time. These tracks are beloved by fans, old and new, for their emotional depth, clever wordplay, and masterful melodies. Whether you’re a longtime admirer or just beginning your journey into Prine’s world, this list will take you on a musical ride through the highlights of his extraordinary career. So, grab a seat, press play, and let the music of John Prine remind us all why he’s one of the greatest songwriters of our time.
1. Angel from Montgomery (1971)
“Angel from Montgomery” stands as one of John Prine’s most cherished songs, first gracing listeners with its poignant lyrics on his self-titled debut album in 1971. The song is told from the perspective of a middle-aged woman who finds herself ensnared in a lackluster marriage, yearning for liberation and the chance to break free from her confining existence. Prine’s storytelling shines through as he articulates her struggles and dreams, capturing the essence of her character with empathy and insight. The image of the “angel” serves as a powerful metaphor for her plea for rescue from her unfulfilling life. With Bonnie Raitt’s iconic cover in 1974, the song soared in popularity, solidifying its status as a folk-country classic. Prine’s ability to evoke deep emotions and resonate with listeners reflects his extraordinary skill as a songwriter. This timeless piece continues to touch the hearts of those who hear it, reminding us all of the longing for connection and freedom, a theme that transcends generations and speaks to the universal human experience.
2. Sam Stone (1971)
“Sam Stone” is a haunting and poignant ballad that delves into the life of a Vietnam War veteran who returns home, only to be haunted by the scars—both physical and emotional—of his experiences. Released in 1971, this song confronts themes of war, addiction, and the ripple effects they have on families with an unflinching sincerity that draws listeners in. One of Prine’s most memorable lines, “There’s a hole in daddy’s arm where all the money goes,” poignantly illustrates the tragedy of addiction, highlighting the heartbreaking reality that many families face. This powerful narrative resonated deeply with audiences during its release and continues to serve as a stark reminder of the costs associated with war. Prine’s sensitive yet raw approach to such a challenging subject matter showcased his courage as a songwriter, not shying away from difficult topics but rather addressing them with grace and authenticity. “Sam Stone” remains an enduring piece that evokes deep reflection on the sacrifices made by veterans and the personal battles they endure long after the war has ended.
3. Paradise (1971)
“Paradise” is a heartfelt tribute to John Prine’s family roots and a lamentation for the environmental devastation inflicted upon his father’s hometown in western Kentucky. Released in 1971, this evocative song narrates the story of a community ravaged by coal mining, particularly at the hands of the Peabody Coal Company. Through Prine’s wistful lyrics, listeners are transported to a nostalgic world that no longer exists, vividly painting images of a simpler, more innocent time in a landscape that has been forever altered. Its emotional weight and relatable themes have made “Paradise” one of Prine’s most enduring songs, frequently performed at live shows and cherished by fans who recognize its environmental and personal significance. The blend of bluegrass and folk influences in the song has solidified its place among country and Americana enthusiasts. “Paradise” serves as a powerful reminder of the importance of preserving our environment while also evoking a sense of longing for lost places, making it not only a favorite among fans but also a poignant commentary on progress and its impact on communities.
4. Hello in There (1971)
“Hello in There” stands out as one of the most touching songs in John Prine’s impressive catalog. Released in 1971, this beautifully crafted track offers a compassionate look at the profound loneliness often experienced in old age. Prine’s ability to empathize with characters much older than himself at the time of writing is remarkable and speaks to his keen understanding of human emotions. The song encourages listeners to notice the elderly, to take a moment to say hello, and to recognize their shared humanity. The lyrics tell the poignant story of an older couple who have outlived their children and are left reminiscing about their past lives filled with love and loss. “Hello in There” serves as a beautifully written call for empathy, reminding us all to connect with those around us, especially the older generation. Its emotional resonance has made it a fan favorite for decades, and its heartfelt message encourages a greater understanding of the elderly’s experiences, making it not just a song, but a gentle plea for compassion and connection in our busy lives.
5. Illegal Smile (1971)
“Illegal Smile,” another gem from Prine’s 1971 debut album, is often interpreted as a lighthearted homage to marijuana, but Prine himself has noted that it’s more about the ability to find joy and escape in an otherwise challenging world. With its upbeat, folk-infused rhythm and clever, playful lyrics, the song quickly won over fans and became a highlight of his early work. The laid-back vibe and humorous undertones stand in contrast to some of the heavier, more serious tracks on the album, showcasing Prine’s remarkable range as a songwriter. “Illegal Smile” captures a sense of whimsy and carefree spirit, providing listeners with a refreshing break from the weight of life’s challenges. Its catchy melody and relatable themes of seeking happiness amid the chaos have ensured its enduring appeal. Over the years, this song has become a symbol of finding lightness in the dark, making it a fun and cherished part of Prine’s legacy, celebrated by listeners who appreciate his ability to weave joy and levity into his music.
6. In Spite of Ourselves (1999)
“In Spite of Ourselves” is a delightful duet featuring Iris DeMent that emerged as one of John Prine’s most beloved songs after its release in 1999. Featured on the album of the same name, this playful track celebrates the quirks of love, imperfections, and the joy found in accepting each other’s flaws. The lyrics are filled with lighthearted banter, where the characters share a humorous take on their relationship, embracing the ups and downs that come with it. The song’s infectious country flair and upbeat energy make it a standout in Prine’s later catalog, showcasing his unique ability to infuse humor into heartfelt narratives. “In Spite of Ourselves” captures the beauty of imperfect love, illustrating that relationships don’t have to be flawless to be meaningful. It stands as a testament to Prine’s skill in writing with both humor and sincerity, resonating with anyone who has experienced the complexities of love. This charming song continues to be a favorite at live shows, reminding fans of the joyful, messy nature of real-life romance.
7. Lake Marie (1995)
Released in 1995 on the album Lost Dogs and Mixed Blessings, “Lake Marie” showcases one of John Prine’s most unique and captivating narratives. The song intricately weaves together seemingly unrelated stories—spanning a troubled relationship, Native American folklore, and a grisly murder mystery—all set against the picturesque backdrop of Lake Marie in Wisconsin. As the song unfolds, these diverse tales intertwine in a mesmerizing manner, capturing the listener’s imagination. Prine’s storytelling prowess shines brightly here, filled with vivid imagery and unexpected twists that keep audiences engaged. The dynamic structure of “Lake Marie,” coupled with its haunting refrain of “We were standing, standing by peaceful waters,” elevates it to one of his most enigmatic and cherished works. This song invites listeners into a world where stories overlap, and emotions run deep, creating a tapestry of life’s complexities and beauty. Its captivating nature continues to resonate with fans, showcasing Prine’s gift for combining intricate narratives with compelling melodies that linger long after the song ends.
8. Clay Pigeons (2005)
“Clay Pigeons” is a cover of Blaze Foley’s 1976 song, but John Prine’s rendition, released in 2005, brought it to a broader audience and made it a standout in his later career. Prine captures the essence of longing and loneliness in the original, but he adds his own unique touch that transforms the song into something special. The lyrics tell the story of a man striving to escape his troubles, seeking solace in the simplicity of life’s small pleasures. Prine’s warm, gravelly voice adds a layer of vulnerability and depth, making the song resonate even more profoundly with listeners. His interpretation of “Clay Pigeons” showcases his ability to breathe new life into an existing song, imbuing it with his characteristic storytelling flair. This track is a perfect example of how Prine could take someone else’s work and make it entirely his own, leaving an indelible mark on the song that reflects his unique perspective and artistry. Fans of both Prine and Foley celebrate this rendition, appreciating how it captures the essence of both artists.
9. Spanish Pipedream (1971)
“Spanish Pipedream” is one of the standout tracks from John Prine’s 1971 debut album, featuring a narrative that blends humor and deeper social commentary. The song tells the story of a disillusioned soldier who meets a stripper, and together they dream of escaping to a simpler, more meaningful life away from societal expectations. The catchy chorus—“Blow up your TV, throw away your paper, go to the country, build you a home”—became an anthem for countercultural living in the 1970s, echoing the sentiments of a generation seeking freedom from the constraints of modern life. With its upbeat tempo and playful lyrics, “Spanish Pipedream” exemplifies Prine’s skill in merging lightheartedness with thought-provoking themes. The song invites listeners to imagine a life unencumbered by the pressures of daily existence, encouraging them to embrace simplicity and connection with nature. Its infectious energy and relatable message resonate with audiences, making it a beloved classic in Prine’s catalog that continues to inspire those longing for a life of authenticity and joy.
10. When I Get to Heaven (2018)
“When I Get to Heaven” was one of the last songs John Prine released before his passing, featured on his 2018 album The Tree of Forgiveness. This whimsical and lighthearted track offers a delightful take on the concept of mortality, as Prine imagines the delightful things he’ll do upon reaching the afterlife—such as drinking whiskey, smoking a cigarette nine miles long, and kissing a beautiful girl. Despite tackling the serious subject of death, the song is infused with joy and humor, showcasing Prine’s unique talent for making even the most profound topics feel approachable and relatable. The lively melody and playful lyrics create an uplifting atmosphere, encouraging listeners to embrace life’s fleeting moments. “When I Get to Heaven” serves as a fitting final gift to his fans, leaving them with a smile and a sense of warmth. This song captures Prine’s unmistakable charm and ability to find light even in the darkest subjects, ensuring that his legacy will be remembered fondly by those who appreciate his artistry and the joy he brought to music.
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.
