John Prine was an American singer-songwriter renowned for his heartfelt and witty lyrics, blending folk, country, and Americana. Born on October 10, 1946, in Maywood, Illinois, Prine’s career spanned over five decades, starting with his self-titled debut album in 1971. Known for songs like “Angel from Montgomery,” “Sam Stone,” and “Hello in There,” he masterfully captured the human condition, often infusing his music with humor and empathy. Prine’s work earned him numerous accolades, including Grammy Awards. He passed away on April 7, 2020, but his legacy continues to influence and inspire musicians worldwide.
1. Angel from Montgomery
“Angel from Montgomery” is one of John Prine’s most beloved songs, first released on his self-titled debut album in 1971. The song tells the story of a middle-aged woman trapped in a mundane, unfulfilled life, longing for escape and a sense of purpose. Its poignant lyrics, written from the perspective of the woman, showcase Prine’s ability to empathize with and articulate the struggles of ordinary people. The song has been widely covered by various artists, including Bonnie Raitt, whose rendition brought it additional acclaim. “Angel from Montgomery” remains a timeless classic, celebrated for its emotional depth and storytelling prowess.
2. Sam Stone
“Sam Stone” by John Prine is a poignant and haunting ballad from his 1971 debut album, *John Prine*. The song tells the tragic story of a Vietnam War veteran who returns home with a heroin addiction, leading to his eventual demise. Prine’s narrative approach and vivid storytelling highlight the devastating effects of war on soldiers and their families.
The lyrics are raw and unflinchingly honest, capturing the sorrow and despair of a man struggling to reintegrate into society. Lines like “There’s a hole in Daddy’s arm where all the money goes” starkly illustrate the pain and loss caused by Sam’s addiction.
Musically, “Sam Stone” features a gentle acoustic guitar and a mournful, melancholic melody that underscore the gravity of the subject matter. Prine’s understated yet emotionally charged delivery brings depth to the narrative, making the song both deeply personal and universally relatable.
“Sam Stone” is celebrated for its unvarnished portrayal of the human cost of war and its empathetic lens on the struggles of returning veterans. It remains one of John Prine’s most powerful and enduring songs, resonating with audiences for its heartfelt depiction of sacrifice and sorrow.
3. Hello in There
“Hello in There” by John Prine is a touching and introspective song from his 1971 debut album, *John Prine*. The song sensitively addresses the loneliness and isolation often experienced by the elderly, a theme not commonly explored in contemporary music.
Written with remarkable empathy and insight, Prine’s lyrics tell the stories of aging individuals who feel forgotten and disconnected from the world around them. The refrain, “Hello in there, hello,” serves as a poignant call for connection and recognition, urging listeners to see and acknowledge the inner lives of older people.
Musically, “Hello in There” features a gentle, melancholic melody supported by Prine’s warm acoustic guitar and understated accompaniment. His vocal delivery is tender and heartfelt, perfectly conveying the song’s emotional weight and sincerity.
Prine’s storytelling shines in this song, as he paints vivid portraits of the characters’ pasts and the quiet pain of their present. Lines like “Old trees just grow stronger, and old rivers grow wilder every day” poetically underscore the depth and resilience of those who have lived long lives, despite their solitude.
“Hello in There” stands as one of John Prine’s most beloved and profound songs, celebrated for its compassionate perspective and its ability to evoke deep empathy and reflection. The song encourages listeners to reach out and connect with those who might otherwise be overlooked, reminding us of the enduring humanity in everyone.
4. Paradise
“Paradise” is a song by John Prine, featured on his debut album released in 1971. The song is a heartfelt lament about the environmental destruction of the singer’s parents’ hometown of Paradise, Kentucky, due to coal mining by the Peabody Coal Company. Prine’s lyrics nostalgically recall the natural beauty of the town before its devastation, highlighting the impact of industrialization on rural communities. “Paradise” is celebrated for its poignant narrative and environmental message, becoming one of Prine’s signature songs. Its timeless appeal has led to numerous covers by various artists, cementing its place in American folk and country music history.
5. That’s the Way That the World Goes ‘Round
“That’s the Way That the World Goes ‘Round” is a popular song by John Prine, released on his 1978 album “Bruised Orange.” The song features Prine’s characteristic wit and humor, addressing the ups and downs of life with a lighthearted, catchy melody. Its lyrics tell stories of everyday struggles and the resilience needed to keep going despite life’s challenges. The song’s upbeat tempo and relatable themes have made it a fan favorite, often performed at Prine’s concerts. “That’s the Way That the World Goes ‘Round” exemplifies Prine’s ability to blend humor with insightful social commentary in his music.
6. In Spite of Ourselves
“In Spite of Ourselves” is a duet by John Prine and Iris DeMent, released as the title track of Prine’s 1999 album. The song is a humorous and endearing portrayal of a quirky, imperfect relationship, highlighting the couple’s flaws and idiosyncrasies while celebrating their love and commitment. With witty and candid lyrics, Prine and DeMent exchange verses that paint a vivid picture of a down-to-earth romance. The song’s playful tone and charming honesty have made it a standout in Prine’s discography, beloved by fans for its warmth and relatability. “In Spite of Ourselves” showcases Prine’s talent for crafting songs that resonate with real-life experiences.
7. Christmas in Prison
“Christmas in Prison” is a song by John Prine, featured on his 1973 album *Sweet Revenge*. The song is a poignant and melancholic ballad that tells the story of a prisoner longing for his lover during the holiday season. Prine’s evocative lyrics describe the stark, cold environment of the prison contrasted with the warmth of his memories and dreams of freedom. The song captures a sense of loneliness and yearning, underscored by a gentle, waltz-like melody. “Christmas in Prison” is celebrated for its emotional depth and Prine’s ability to convey complex feelings with simplicity and grace, making it a cherished piece in his repertoire.
8. Souvenirs
“Souvenirs” by John Prine is a reflective and wistful song, originally featured on his 1972 album *Diamonds in the Rough* and later revisited on his 2000 album *Souvenirs*. The song delves into themes of memory, nostalgia, and the passage of time, capturing the bittersweet nature of holding onto mementos from the past.
In “Souvenirs,” Prine’s lyrics weave a narrative of looking back on life’s moments and the objects that symbolize them. Lines like “Memories, they can’t be boughten / They can’t be won at carnivals for free” poignantly highlight the irreplaceable value of personal experiences and the tangible items that help keep those memories alive.
Musically, the song is characterized by its simple yet evocative arrangement, featuring acoustic guitar and subtle harmonica that complement Prine’s warm and earthy vocals. The melody is gentle and soothing, creating a contemplative backdrop for the song’s introspective lyrics.
Prine’s delivery in “Souvenirs” is marked by a mix of melancholy and fondness, as he navigates the emotional landscape of remembering the past while acknowledging the inevitable changes brought by time. The song’s refrain, “I hate graveyards and old pawn shops / For they always bring me tears,” captures the heartache associated with the ephemeral nature of life and the longing for what once was.
“Souvenirs” resonates deeply with listeners for its universal theme of cherishing life’s fleeting moments and the tangible reminders of them. It stands as a testament to John Prine’s ability to craft songs that are both deeply personal and broadly relatable, touching on the delicate balance between holding on to memories and moving forward.
9. All the Best
“All the Best” is a song by John Prine from his 1991 album *The Missing Years*. The song reflects on the end of a relationship, offering a mix of sorrow, resignation, and a genuine wish for the former partner’s happiness. Prine’s lyrics are heartfelt and direct, conveying the complexities of parting ways while still caring for someone. With its gentle melody and sincere tone, “All the Best” showcases Prine’s talent for capturing human emotions with honesty and empathy. The song remains a favorite among fans, appreciated for its introspective nature and the depth of feeling it conveys.
10. Illegal Smile
“Illegal Smile” by John Prine is an iconic and playful tune from his self-titled 1971 debut album, *John Prine*. The song stands out for its witty lyrics and light-hearted take on personal freedom and finding joy amidst life’s challenges.
While often interpreted as a humorous nod to marijuana use, “Illegal Smile” can also be seen as a broader commentary on the simple, sometimes subversive pleasures that help people cope with the pressures and absurdities of everyday life. Prine’s lyrics capture this spirit with lines like “Well, I woke up this morning / And I got myself a beer / The future’s uncertain / And the end is always near.”
Musically, the song features an upbeat folk melody, with Prine’s acoustic guitar playing providing a cheerful and catchy backdrop. His vocal delivery is relaxed and amiable, inviting listeners to share in the amusement and light-heartedness of the song.
The refrain, “And you may see me tonight with an illegal smile / It don’t cost very much, but it lasts a long while,” encapsulates the song’s playful defiance and the joy of finding small moments of happiness, even in the face of societal expectations or constraints.
“Illegal Smile” is celebrated for its clever wordplay and its ability to bring a smile to the listener’s face. It showcases John Prine’s talent for blending humor with insightful observations about life and individuality. The song remains a beloved part of Prine’s repertoire, embodying his unique voice and the enduring appeal of his 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.
