John Prine was a highly influential American singer-songwriter known for his distinctive voice, witty and poignant lyrics, and storytelling prowess. Born in 1946 in Maywood, Illinois, Prine emerged in the early 1970s as part of the folk and country music scenes.
His songs often explored themes of everyday life, love, humor, and social commentary with a keen observational eye. Tracks like “Angel from Montgomery,” “Sam Stone,” and “Hello in There” became classics, showcasing his ability to blend humor and heartache in his storytelling.
Prine’s music resonated deeply with audiences and fellow musicians alike for its honesty and authenticity. He received numerous accolades throughout his career, including multiple Grammy Awards and induction into the Songwriters Hall of Fame. His passing in 2020 left a profound impact on the music world, solidifying his legacy as a masterful songwriter and beloved troubadour.
1. Angel from Montgomery
“Angel from Montgomery” is a poignant folk song written by John Prine, first appearing on his 1971 self-titled debut album. The song has been widely covered by various artists and is considered one of Prine’s signature songs.
The lyrics of “Angel from Montgomery” depict the inner thoughts and reflections of a middle-aged woman living a mundane life in a small town. She yearns for an escape from her daily routine and dreams of a better life, reflecting on her unfulfilled hopes and desires. The song’s narrative is deeply introspective and captures themes of longing, regret, and the search for meaning.
Musically, “Angel from Montgomery” features a gentle acoustic guitar melody and Prine’s emotive vocals, creating a melancholic and introspective atmosphere. The chorus, where the protagonist laments “just give me one thing that I can hold on to,” underscores the song’s sense of longing and emotional depth.
“Angel from Montgomery” has become a classic of folk and Americana music, celebrated for its poignant lyrics, evocative storytelling, and John Prine’s ability to capture universal human experiences with empathy and insight.
2. Sam Stone
“Sam Stone” is a song written by John Prine and included on his 1971 self-titled debut album. The song tells the story of a Vietnam War veteran who returns home with a drug addiction, ultimately leading to his death from an overdose. The lyrics paint a vivid picture of Sam Stone’s struggles, portraying the devastating effects of war on individuals and their families.
“Sam Stone” is praised for its poignant storytelling and emotional depth, tackling themes of addiction, trauma, and the impact of war with empathy and insight. The song’s simple yet powerful melody, coupled with Prine’s heartfelt delivery, resonated with audiences and solidified Prine’s reputation as a masterful songwriter. “Sam Stone” remains one of Prine’s most enduring and influential songs, earning a place in the pantheon of folk and Americana music.
3. Hello in There
“Hello in There” is a poignant and introspective song written by John Prine, appearing on his self-titled debut album released in 1971. The song is known for its empathetic portrayal of loneliness, aging, and the passage of time.
The lyrics of “Hello in There” tell the story of elderly individuals living in a small town, reflecting on their lives and the loneliness they experience. Prine’s narrative style is compassionate and sensitive, capturing the humanity and dignity of the characters as they cope with isolation and the feeling of being forgotten.
Musically, “Hello in There” features a gentle acoustic guitar accompaniment and Prine’s heartfelt vocals, creating a somber and reflective mood. The chorus, where Prine sings “you know that old trees just grow stronger, and old rivers grow wilder every day,” reinforces the song’s themes of resilience and the inevitability of aging.
“Hello in There” has resonated deeply with audiences for its universal themes and emotional depth. It has been covered by numerous artists over the years and remains a timeless example of John Prine’s ability to capture the human condition with empathy and grace.
4. Paradise
“Paradise” is a song by John Prine, released on his 1971 self-titled debut album. The song is a poignant and nostalgic look at the impact of strip mining on the environment and the loss of a way of life in rural America. The lyrics are inspired by Prine’s own experiences visiting his grandparents in Kentucky and seeing the effects of coal mining on the land.
“Paradise” is characterized by its simple yet powerful melody and Prine’s heartfelt delivery. The song’s chorus, which laments, “Daddy, won’t you take me back to Muhlenberg County, down by the Green River where Paradise lay,” has become particularly iconic. “Paradise” is considered one of Prine’s signature songs and has been covered by numerous artists, cementing its status as a classic in the folk and Americana genres.
5. That’s the Way That the World Goes ‘Round
“That’s the Way That the World Goes ‘Round” is a song by John Prine from his 1978 album “Bruised Orange.” Known for its playful and witty lyrics, the song offers a humorous take on life’s unpredictability and absurdities.
The lyrics of “That’s the Way That the World Goes ‘Round” depict various quirky and surreal scenarios, such as a father who waters his lawn in the rain and a woman who files for divorce from her husband because he lost interest in her. Despite these oddities, the song’s underlying message is one of acceptance and resilience in the face of life’s ups and downs.
Musically, the song features a jaunty acoustic guitar melody and Prine’s laid-back, conversational vocal delivery. The upbeat tempo and cheerful instrumentation contrast with the sometimes darkly humorous lyrics, creating an engaging and light-hearted atmosphere.
“That’s the Way That the World Goes ‘Round” has become one of John Prine’s most beloved and enduring songs, celebrated for its clever wordplay, infectious melody, and insightful commentary on the human experience. It exemplifies Prine’s unique ability to blend humor with profound observations about life, making it a timeless classic in folk and Americana music.
6. In Spite of Ourselves
“In Spite of Ourselves” is a song written and recorded by John Prine, featuring vocals from country music artist Iris DeMent. It was released in 1999 as the title track of Prine’s album *In Spite of Ourselves*. The song is a humorous and irreverent take on love and relationships, with the lyrics describing a couple who are deeply flawed but love each other unconditionally.
“In Spite of Ourselves” is characterized by its playful lyrics, catchy melody, and the chemistry between Prine and DeMent’s voices. The song’s chorus, which proclaims, “In spite of ourselves, we’ll end up a-sittin’ on a rainbow,” has become particularly memorable. “In Spite of Ourselves” has been praised for its witty lyrics and infectious charm, showcasing Prine’s talent for storytelling and humor.
7. Christmas in Prison
“Christmas in Prison” is a song by John Prine from his 1973 album “Sweet Revenge.” It’s a poignant and introspective ballad that reflects on loneliness, longing, and the passage of time during the holiday season.
The lyrics of “Christmas in Prison” paint a vivid picture of a prisoner spending Christmas behind bars. Prine’s narrative is rich with imagery, describing the melancholy atmosphere of the prison, the longing for freedom, and the memories of past holidays spent with loved ones. Despite the somber setting, there’s a sense of warmth and nostalgia in the way Prine captures the essence of Christmas and the yearning for connection.
Musically, the song features a gentle acoustic guitar accompaniment and Prine’s emotive vocals, which convey a sense of longing and reflection. The melody is melancholic yet comforting, evoking a bittersweet mood that resonates with listeners.
“Christmas in Prison” has been praised for its evocative storytelling, heartfelt lyrics, and Prine’s ability to capture the emotional complexities of life. It has become a favorite among fans of Prine’s music and is celebrated as a poignant meditation on the meaning of Christmas and the human experience of longing and hope.
8. Souvenirs
“Souvenirs” is a song by John Prine, released on his 1972 album *Diamonds in the Rough*. The song reflects on memories and lost love, with Prine reminiscing about a past relationship and the souvenirs that evoke those memories. The lyrics paint a vivid picture of the emotions tied to these mementos, capturing the nostalgia and bittersweetness of looking back on the past.
“Souvenirs” is characterized by its introspective lyrics, gentle melody, and Prine’s heartfelt delivery. The song’s chorus, which repeats the line “Memories, they can’t be boughten, they can’t be won at carnivals for free,” has become particularly memorable. “Souvenirs” is considered one of Prine’s signature songs, showcasing his ability to convey deep emotions and tell compelling stories through his music.
9. All the Best
“All the Best” is a song written by John Prine, featured on his 1991 album “The Missing Years.” The song is notable for its warm, humorous, and heartfelt lyrics, delivered in Prine’s distinctive folk-country style.
Lyrically, “All the Best” is a farewell letter of sorts, where Prine humorously bids goodbye to someone who is leaving or ending a relationship. The lyrics are filled with witty wordplay and clever turns of phrase, expressing good wishes and acknowledging the complexities of life and relationships. Despite the farewell theme, the song maintains a light-hearted and optimistic tone.
Musically, “All the Best” features a gentle acoustic guitar melody and Prine’s laid-back, conversational vocal delivery. The song’s simple yet effective instrumentation and Prine’s warm vocals create an intimate and inviting atmosphere.
“All the Best” has been praised for its charming lyrics, catchy melody, and Prine’s ability to blend humor with genuine emotion. It has become a favorite among fans and is celebrated as one of John Prine’s signature songs, showcasing his wit, wisdom, and storytelling prowess in the realm of folk and Americana music.
10. Illegal Smile
“Illegal Smile” is a song by John Prine, featured on his self-titled debut album released in 1971. The song is known for its playful and whimsical lyrics, exploring the idea of finding joy and escape through humor and imagination.
The lyrics of “Illegal Smile” reflect on the narrator’s experiences with feeling down or lonely, and how a simple smile or sense of humor can lift one’s spirits. The title refers to the euphoric feeling that comes from finding solace in laughter or a positive outlook, despite life’s challenges.
Musically, “Illegal Smile” features a mellow acoustic guitar arrangement and Prine’s laid-back, wistful vocals. The song’s gentle melody and introspective lyrics create a relaxed and contemplative atmosphere, inviting listeners to reflect on the power of laughter and optimism.
“Illegal Smile” has become a beloved song among John Prine fans for its quirky charm, clever wordplay, and insightful commentary on finding happiness in unexpected places. It exemplifies Prine’s ability to blend humor with depth and sincerity, making it a timeless gem in the realm of folk and Americana music.