John Prine’s music resonates deeply with listeners, blending heartfelt storytelling with poignant melodies that capture the essence of human experiences. As a revered figure in folk and country music, Prine’s songs are cherished for their wit, wisdom, and emotional depth. This article explores the top ten best John Prine songs of all time, showcasing his exceptional talent and enduring influence on the music scene.
Prine’s songwriting prowess is evident in his ability to craft narratives that are both profound and relatable. From the humor of “Illegal Smile” to the melancholy of “Hello in There,” each song offers a glimpse into the complexities of life, love, and loss. His unique perspective and lyrical craftsmanship have earned him a devoted following and critical acclaim.
Among the standout tracks are “Angel from Montgomery,” a soulful reflection on dreams deferred, and “Sam Stone,” a haunting portrayal of a Vietnam War veteran’s struggles. “Paradise” paints a nostalgic picture of a vanishing way of life, while “In Spite of Ourselves” showcases Prine’s playful side in a duet with Iris DeMent. These songs, along with others on the list, showcase Prine’s ability to touch hearts and minds with his music, solidifying his place as one of the greatest songwriters of his generation.
1. Sam Stone
“Sam Stone” is often regarded as one of John Prine’s most powerful and iconic songs. Released on his 1971 self-titled debut album, the track tells the poignant story of a Vietnam War veteran struggling with addiction and the psychological scars of war. Prine’s empathetic storytelling and vivid imagery paint a haunting picture of the hardships faced by many veterans, making it a deeply moving and socially relevant song.
The song’s emotional impact is heightened by Prine’s raw and heartfelt delivery, as well as the sparse, acoustic arrangement that allows the lyrics to take center stage. “Sam Stone” showcases Prine’s ability to tackle complex and sensitive subjects with grace and compassion, earning him a reputation as one of the greatest songwriters of his generation.
Over the years, “Sam Stone” has resonated with listeners around the world and has become a classic in Prine’s repertoire. Its timeless message about the human cost of war and the struggles of returning veterans continues to strike a chord with audiences, cementing its place as one of the most popular and enduring songs in John Prine’s remarkable career.
2. That’s the Way That the World Goes Round
“That’s the Way That the World Goes Round” is a standout track from John Prine’s critically acclaimed album “Bruised Orange,” released in 1978. The song is a whimsical and satirical take on life’s unpredictability, with Prine’s signature wit and humor shining through in the lyrics.
The song’s upbeat melody and catchy chorus, combined with Prine’s laid-back vocal delivery, give it an infectious charm that makes it a favorite among fans. Despite its lighthearted tone, “That’s the Way That the World Goes Round” also contains a deeper message about resilience and acceptance in the face of life’s ups and downs.
Prine’s ability to blend humor with profound observations about the human experience is on full display in this song, showcasing why he is considered one of the greatest songwriters of his generation. “That’s the Way That the World Goes Round” has endured as one of Prine’s most beloved songs, beloved for its catchy melody, clever lyrics, and timeless message about the nature of life.
3. When I Get to Heaven
“When I Get to Heaven” is a poignant and uplifting song from John Prine’s final album, “The Tree of Forgiveness,” released in 2018. The song reflects on Prine’s life and legacy with a mix of humor, nostalgia, and hope for the afterlife.
In “When I Get to Heaven,” Prine imagines a joyous reunion with loved ones who have passed away, as well as indulging in some of life’s simple pleasures, like smoking a cigarette that’s nine miles long and drinking a cocktail called “Electricity.” The song’s cheerful melody and upbeat tempo create a celebratory atmosphere, making it a fitting conclusion to Prine’s storied career.
Despite dealing with heavy themes like mortality and the afterlife, “When I Get to Heaven” is ultimately a song of joy and acceptance, reflecting Prine’s resilient and optimistic outlook on life. The song’s catchy chorus and infectious energy make it a standout track on an album that was hailed as a triumphant return for Prine after a long battle with cancer.
“When I Get to Heaven” stands as a testament to John Prine’s talent as a songwriter and his ability to find beauty and humor in life’s most challenging moments.
4. In Spite of Ourselves
“In Spite of Ourselves” is a charming duet featuring John Prine and Iris DeMent, released on Prine’s album of the same name in 1999. The song is a playful and lighthearted take on love and relationships, with Prine and DeMent’s voices blending beautifully to create a delightful and heartfelt duet.
The lyrics of “In Spite of Ourselves” tell the story of a quirky and unconventional couple who, despite their flaws and differences, find love and happiness in each other’s company. The song’s humorous and often risqué lyrics, paired with Prine and DeMent’s playful delivery, give it a unique and endearing charm that has made it a fan favorite.
“In Spite of Ourselves” showcases Prine’s talent for storytelling and his knack for writing songs that resonate with audiences on a deeply personal level. The song’s catchy melody and infectious chorus make it a joy to listen to, while its witty lyrics and quirky charm make it a standout track in Prine’s extensive catalog.
Overall, “In Spite of Ourselves” is a delightful and heartwarming song that highlights John Prine’s unique ability to capture the complexities of love and relationships with humor and sincerity.
5. Fish and Whistle
“Fish and Whistle” is a delightful track from John Prine’s album “Bruised Orange,” released in 1978. The song features Prine’s signature blend of humor and insight, with witty lyrics that reflect on life’s simple pleasures and the passage of time.
In “Fish and Whistle,” Prine sings about the ups and downs of life, using playful imagery like “blow up your TV” and “plant a little garden” to convey his message of finding joy in the everyday moments. The song’s catchy melody and upbeat tempo make it a joyous and uplifting listen, while Prine’s laid-back vocal delivery adds to its charm.
“Fish and Whistle” is a testament to Prine’s talent as a songwriter, with its clever wordplay and poignant observations about life’s unpredictability. The song’s optimistic outlook and catchy chorus have made it a favorite among fans, and it remains a beloved track in Prine’s extensive discography.
Overall, “Fish and Whistle” is a charming and insightful song that showcases John Prine’s unique ability to find beauty and meaning in life’s simplest pleasures.
6. Some Humans Ain’t Human
“Some Humans Ain’t Human” is a poignant and thought-provoking song from John Prine’s album “Fair & Square,” released in 2005. The song features Prine’s signature storytelling style, with lyrics that offer a critical and sometimes cynical view of human nature.
In “Some Humans Ain’t Human,” Prine reflects on the darker aspects of humanity, highlighting examples of cruelty, hypocrisy, and injustice in the world. The song’s sparse arrangement and Prine’s soulful vocals give it a haunting quality, emphasizing the weight of the song’s message.
Despite its somber tone, “Some Humans Ain’t Human” also contains a message of hope and redemption, with Prine reminding listeners that kindness and compassion can still prevail in a world filled with cruelty. The song’s powerful lyrics and emotional depth have resonated with audiences, making it a standout track in Prine’s later discography.
Overall, “Some Humans Ain’t Human” is a powerful and introspective song that showcases John Prine’s ability to tackle complex and challenging subjects with grace and insight. It is a testament to Prine’s enduring talent as a songwriter and his ability to touch the hearts of listeners with his music.
7. Hello in There
“Hello in There” is a poignant and introspective song from John Prine’s self-titled debut album, released in 1971. The song is a moving portrayal of loneliness and isolation, with Prine’s empathetic lyrics painting a vivid picture of an elderly couple who feel invisible and forgotten by the world around them.
In “Hello in There,” Prine sings from the perspective of the elderly couple, offering a glimpse into their lives and the struggles they face. The song’s gentle melody and Prine’s tender vocals create a melancholic and reflective mood, evoking empathy and compassion from the listener.
“Hello in There” is widely regarded as one of Prine’s most powerful and emotionally resonant songs, with its universal theme of human connection transcending generations. The song’s message about the importance of empathy and understanding towards the elderly is as relevant today as it was when it was first written, making it a timeless classic in Prine’s repertoire.
Overall, “Hello in There” is a beautiful and moving song that showcases John Prine’s talent for storytelling and his ability to capture the complexities of the human experience with grace and compassion.
8. Dear Abby
“Dear Abby” is a humorous and satirical song from John Prine’s album “Sweet Revenge,” released in 1973. The song is written in the form of a letter to advice columnist Dear Abby, with Prine offering a series of outlandish and absurd problems for her to solve.
In “Dear Abby,” Prine tackles a variety of social issues and taboos with his trademark wit and irreverence, touching on topics like infidelity, addiction, and social awkwardness. The song’s catchy melody and playful lyrics make it a fun and entertaining listen, while Prine’s deadpan delivery adds to its comedic effect.
Despite its humorous tone, “Dear Abby” also contains a deeper message about the absurdity of some of society’s conventions and the importance of being able to laugh at ourselves. The song’s clever wordplay and satirical edge have made it a favorite among fans, and it remains a beloved track in Prine’s catalog.
Overall, “Dear Abby” is a light-hearted and humorous song that showcases John Prine’s unique ability to tackle serious subjects with humor and wit. It is a testament to Prine’s talent as a songwriter and his knack for finding humor in life’s most absurd moments.
9. Grandpa Was a Carpenter
“Grandpa Was a Carpenter” is a heartwarming and nostalgic song from John Prine’s album “Sweet Revenge,” released in 1973. The song pays tribute to Prine’s grandfather, celebrating his life and the legacy he left behind.
In “Grandpa Was a Carpenter,” Prine reminisces about his grandfather’s life and the impact he had on those around him. The song paints a vivid picture of a hardworking and kind-hearted man who lived life to the fullest, leaving a lasting impression on everyone he met.
Prine’s affectionate lyrics and soulful vocals give the song a heartfelt and emotional quality, making it a touching tribute to his grandfather. The song’s upbeat tempo and catchy chorus add to its charm, making it a joyous and uplifting listen.
“Grandpa Was a Carpenter” is a testament to the power of family and the importance of honoring our loved ones’ legacies. It is a beautiful and heartfelt song that showcases John Prine’s talent for storytelling and his ability to capture the essence of the human experience with warmth and sincerity.
10. Illegal Smile
“Illegal Smile” is a whimsical and light-hearted song from John Prine’s self-titled debut album, released in 1971. The song is known for its playful lyrics and catchy melody, as well as its tongue-in-cheek exploration of the concept of happiness.
In “Illegal Smile,” Prine sings about finding joy and contentment in the simple things in life, like a “good, good morning” or a “walk in the park.” The song’s title refers to the act of smiling without a specific reason, suggesting a kind of rebellious happiness that defies societal norms.
Despite its seemingly light-hearted tone, “Illegal Smile” also contains a deeper message about the nature of happiness and the importance of finding joy in the little moments. Prine’s laid-back vocal delivery and the song’s mellow arrangement give it a relaxed and carefree vibe, making it a favorite among fans.
Overall, “Illegal Smile” is a charming and whimsical song that showcases John Prine’s unique perspective and his ability to find beauty and humor in life’s everyday moments. It is a song that invites listeners to embrace the joy of living and to find happiness wherever they can.