John Prine was a revered American singer-songwriter known for his poignant lyrics, wry humor, and distinctive voice. Born on October 10, 1946, in Maywood, Illinois, Prine emerged in the early 1970s as a leading figure in the folk and Americana music scenes. His songwriting prowess earned him widespread acclaim, with songs like “Angel from Montgomery,” “Hello in There,” and “Paradise” becoming classics.
Prine’s music often explored themes of love, loss, human frailty, and social issues, delivered with a blend of sincerity and wit. His storytelling ability and knack for capturing life’s complexities endeared him to audiences worldwide. Despite battling cancer in later years, Prine continued to create music until his passing on April 7, 2020, leaving behind a profound legacy that continues to inspire generations of musicians and fans alike.
1. Angel from Montgomery
“Angel from Montgomery” is a timeless folk ballad written by John Prine, first released on his self-titled debut album in 1971. The song has since become one of Prine’s most iconic compositions, covered by numerous artists across different genres.
“Angel from Montgomery” tells the story of a woman longing for escape and redemption from her mundane life. Through vivid imagery and heartfelt lyrics, the song explores themes of longing, regret, and the search for meaning. The protagonist reflects on her unfulfilled dreams and desires, yearning for a better existence and contemplating the possibility of divine intervention.
With its haunting melody and evocative storytelling, “Angel from Montgomery” exemplifies Prine’s songwriting genius and his ability to convey profound emotions with simplicity and depth. The song’s universal themes and timeless appeal have cemented its status as a classic in the folk music canon, earning it recognition as one of Prine’s most enduring and beloved works.
2. Sam Stone
“Sam Stone” is a poignant and powerful song written by John Prine, released on his self-titled debut album in 1971. The song tells the story of a Vietnam War veteran who returns home with physical and psychological scars, struggling with addiction and despair. Prine’s raw and emotive vocals, coupled with his vivid storytelling and poignant lyrics, paint a haunting picture of the human cost of war and its aftermath. “Sam Stone” is widely regarded as one of Prine’s signature songs, praised for its social commentary and emotional depth. It remains a timeless reminder of the toll of war on individuals and families, resonating with audiences for generations.
3. Hello in There
“Hello in There” is a poignant and introspective song written by John Prine, featured on his self-titled debut album released in 1971. The song delicately captures the loneliness and isolation experienced by elderly individuals, offering a compassionate portrayal of aging and the passage of time.
Through its gentle melody and tender lyrics, “Hello in There” invites listeners to empathize with the quiet struggles of elderly people who often feel invisible or overlooked by society. Prine’s empathetic storytelling and vivid imagery paint a vivid picture of lives marked by unfulfilled dreams, forgotten ambitions, and the weight of solitude.
As the song unfolds, Prine’s emotive vocals and simple yet profound lyrics convey a deep sense of empathy and understanding, urging listeners to recognize the humanity and dignity of every individual, regardless of age or circumstance. “Hello in There” remains a timeless masterpiece that continues to resonate with audiences, serving as a poignant reminder to cherish and honor the elderly among us.
4. Paradise
“Paradise” is a classic folk song written by John Prine, featured on his self-titled debut album released in 1971. The song recounts Prine’s childhood memories of visiting his grandparents’ hometown of Paradise, Kentucky, which had been ravaged by strip mining. Through vivid storytelling and poignant imagery, Prine captures the loss of innocence and the destruction of nature caused by industrialization. “Paradise” is celebrated for its heartfelt lyrics, simple melody, and Prine’s distinctive vocal delivery. It has become one of Prine’s most beloved and enduring songs, resonating with listeners for its timeless themes of nostalgia, environmentalism, and the human connection to the land.
5. That’s the Way That the World Goes ‘Round
“That’s the Way That the World Goes ‘Round” is a whimsical and insightful song written by John Prine, featured on his album “Bruised Orange” released in 1978. The song presents a humorous yet poignant reflection on life’s unpredictability and the ups and downs we all experience. With its catchy melody and clever wordplay, “That’s the Way That the World Goes ‘Round” captures the irony and absurdity of everyday situations. Prine’s distinctive voice and playful delivery add depth and charm to the song, making it a favorite among fans. Its universal message about acceptance and resilience resonates across generations, solidifying its place as one of Prine’s most enduring compositions.
6. In Spite of Ourselves
“In Spite of Ourselves” is a charming and humorous duet written by John Prine, featured on his album of the same name released in 1999. The song features Prine’s signature wit and storytelling, exploring the ups and downs of a quirky and imperfect romantic relationship. With its catchy melody and clever lyrics, “In Spite of Ourselves” celebrates the enduring love between two imperfect individuals who find solace and joy in each other’s company. The song’s playful tone and heartfelt sentiment make it a favorite among fans of Prine’s music. Additionally, the duet version with Iris DeMent adds depth and chemistry to the song, further enhancing its appeal.
7. Christmas in Prison
“Christmas in Prison” is a soulful and melancholic holiday song penned by John Prine, featured on his album “Sweet Revenge,” released in 1973. Unlike traditional cheerful Christmas tunes, “Christmas in Prison” offers a more introspective and bittersweet perspective on the holiday season.
The song tells the story of a narrator spending Christmas behind bars, longing for the warmth and comfort of home. Through its evocative lyrics and tender melody, “Christmas in Prison” captures the longing for connection and the sense of isolation experienced by those separated from their loved ones during the holidays.
Prine’s emotive vocals and heartfelt delivery convey the narrator’s yearning for freedom and the simple joys of being with family and friends. Despite the somber subject matter, the song also carries a message of hope and resilience, emphasizing the enduring power of love and the human spirit even in the darkest of times.
With its poignant lyrics and haunting melody, “Christmas in Prison” stands as a testament to John Prine’s songwriting prowess and his ability to infuse even the most somber subjects with beauty and depth.
8. Souvenirs
“Souvenirs” is a poignant and reflective song by John Prine, featured on his album “Diamonds in the Rough” released in 1972. The song captures the bittersweet nostalgia of reminiscing about past memories and experiences. Through vivid imagery and heartfelt lyrics, Prine evokes the passage of time and the sentimental value we attach to keepsakes and mementos. “Souvenirs” showcases Prine’s songwriting prowess and ability to convey complex emotions with simplicity and honesty. With its gentle melody and soulful delivery, the song resonates deeply with listeners, serving as a reminder of the beauty and poignancy of life’s fleeting moments.
9. All the Best
“All the Best” is a heartfelt and humorous song by John Prine, featured on his album “The Missing Years,” released in 1991. Written by Prine and his longtime friend and collaborator, Pat McLaughlin, the song reflects on the end of a relationship with a mixture of wistfulness and optimism.
Through its catchy melody and clever wordplay, “All the Best” tells the story of a couple parting ways, with the narrator wishing their former partner well on their journey ahead. Despite the sadness of saying goodbye, there’s a sense of acceptance and goodwill conveyed throughout the song.
Prine’s signature wit and charm shine through in the lyrics, as he humorously acknowledges the challenges of love and life’s uncertainties. The song’s upbeat tempo and infectious chorus make it a standout track on the album, showcasing Prine’s ability to blend poignant storytelling with lighthearted humor.
With its universal themes of love, loss, and resilience, “All the Best” has resonated with audiences for its relatable lyrics and uplifting message of moving forward with grace and goodwill.
10. Illegal Smile
“Illegal Smile” is a whimsical and lighthearted song by John Prine, featured on his self-titled debut album released in 1971. The song’s playful lyrics explore the notion of finding joy and solace in life’s simple pleasures, even in situations where one might feel down or overwhelmed. With its catchy melody and clever wordplay, “Illegal Smile” has become one of Prine’s most beloved and iconic songs. Despite its title suggesting something illicit, the song’s true message is about finding happiness and laughter amidst life’s challenges. Prine’s distinctive voice and charming delivery add depth and warmth to the song, making it a favorite among fans and a staple of his live performances.
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.
