John Prine was a legendary American singer-songwriter known for his unique blend of folk, country, and Americana music. Born on October 10, 1946, in Maywood, Illinois, Prine gained acclaim for his witty and poignant lyrics, often infused with humor and a keen observation of human nature. Some of his most famous songs include “Angel from Montgomery,” “Paradise,” “Hello in There,” and “Sam Stone.”
Prine’s career spanned several decades, during which he released numerous albums and won multiple Grammy Awards. His songwriting prowess earned him widespread admiration among fellow musicians and fans alike, and he was often regarded as one of the most influential songwriters of his generation.
Unfortunately, John Prine passed away on April 7, 2020, due to complications from COVID-19. His legacy, however, continues to live on through his timeless music, which continues to inspire and resonate with audiences around the world.
1. Angel from Montgomery
“Angel from Montgomery” is one of John Prine’s most beloved and iconic songs, originally released on his 1971 self-titled debut album. The song has since been covered by numerous artists and has become a staple of Americana music.
“Angel from Montgomery” is a poignant narrative about a woman trapped in a mundane and unfulfilling life, yearning for something more. The lyrics vividly depict her longing for escape and redemption, as she dreams of being freed from her daily struggles. The refrain “Make me an angel that flies from Montgomery” reflects her desire for transcendence and liberation from her circumstances.
The song’s emotional depth, coupled with Prine’s soulful delivery and masterful storytelling, has made “Angel from Montgomery” a timeless classic that continues to resonate with listeners across generations.
2. Sam Stone
“Sam Stone” is another iconic song by John Prine, featured on his self-titled debut album released in 1971. The song tells the heartbreaking story of a Vietnam War veteran who returns home with physical and emotional scars, struggling with addiction to cope with the trauma he experienced.
The lyrics paint a vivid portrait of Sam Stone, a soldier who becomes addicted to drugs to numb the pain of war memories and the loss of his friends. Despite his family’s efforts to support him, Sam ultimately succumbs to his addiction, leading to his tragic demise.
The chorus of the song hauntingly repeats the lines “There’s a hole in Daddy’s arm where all the money goes / Jesus Christ died for nothin’, I suppose.” These lines poignantly capture the despair and disillusionment felt by Sam and serve as a stark commentary on the devastating impact of war on individuals and families.
“Sam Stone” is widely regarded as one of John Prine’s most powerful and emotionally resonant songs, showcasing his ability to tackle complex social issues with empathy and insight.
3. Hello in There
“Hello in There” is a poignant and introspective song by John Prine, released on his self-titled debut album in 1971. The song explores themes of loneliness, aging, and the human experience with a depth of empathy and compassion.
In “Hello in There,” Prine sings from the perspective of an elderly couple who feel isolated and overlooked by society. The lyrics delve into the quiet struggles of aging, as the couple reflects on their lives, memories, and the passage of time. Despite their longing for connection, they often find themselves ignored or dismissed by those around them.
4. Paradise
“Paradise” is a classic song written by John Prine, featured on his self-titled debut album released in 1971. The song is a nostalgic tribute to Prine’s hometown of Paradise, Kentucky, which was affected by strip mining.
In “Paradise,” Prine reminisces about his childhood memories of Paradise, describing it as a beautiful and idyllic place where he spent his summers. However, he also laments the environmental destruction caused by strip mining, which led to the loss of the town’s natural beauty and forced many residents to leave their homes.
5. That’s the Way That the World Goes ‘Round
“That’s the Way That the World Goes ‘Round” is a lively and whimsical song written by John Prine, featured on his 1978 album “Bruised Orange.” The song’s upbeat tempo and playful lyrics explore the unpredictable and sometimes absurd nature of life.
In “That’s the Way That the World Goes ‘Round,” Prine muses on various quirky and unexpected events that occur in everyday life. The lyrics paint a colorful picture of the world’s randomness and absurdities, from unexpected encounters to peculiar situations.
The chorus of the song, with its catchy refrain of “That’s the way that the world goes ’round / You’re up one day and the next you’re down,” encapsulates the song’s central theme of embracing life’s highs and lows with a sense of humor and resilience.
With its infectious melody and witty wordplay, “That’s the Way That the World Goes ‘Round” has become one of John Prine’s most beloved and enduring songs, celebrated for its irreverent charm and universal appeal.
6. In Spite of Ourselves
“In Spite of Ourselves” is a humorous and charming song written by John Prine, which also serves as the title track of his 1999 album. The song features Prine duetting with country music singer Iris DeMent.
The lyrics of “In Spite of Ourselves” tell the story of a couple deeply in love despite their quirks and imperfections. Each verse humorously highlights the idiosyncrasies and flaws of the couple, but the chorus reinforces the enduring nature of their love, singing, “In spite of ourselves, we’ll end up a-sittin’ on a rainbow / Against all odds, honey, we’re the big door prize.”
The song’s witty lyrics and catchy melody, combined with the chemistry between Prine and DeMent, make “In Spite of Ourselves” a delightful and memorable tune that celebrates the ups and downs of relationships with humor and warmth.
7. Christmas in Prison
“Christmas in Prison” is a poignant and evocative song written by John Prine, featured on his 1973 album “Sweet Revenge.” The song paints a vivid picture of spending Christmas behind bars, capturing the longing for freedom and the bittersweet emotions of being separated from loved ones during the holiday season.
In “Christmas in Prison,” Prine’s narrator reflects on his time spent incarcerated during the holiday season. Despite the somber setting, there is a sense of warmth and camaraderie among the inmates, as they come together to celebrate and find solace in each other’s company. The song’s lyrics are filled with vivid imagery, from the flickering candlelight to the sound of carols echoing through the halls.
Throughout the song, Prine conveys a mix of nostalgia, longing, and resignation, as the narrator yearns for the simple joys of Christmas and dreams of being reunited with loved ones. Despite the hardships of prison life, there is a sense of hope and resilience in the narrator’s voice, making “Christmas in Prison” a poignant and moving reflection on the power of love and community during difficult times.
8. Souvenirs
“Souvenirs” is a poignant song written by John Prine, featured on his 1972 album “Diamonds in the Rough.” The song reflects on the passage of time and the bittersweet memories that accompany it.
In “Souvenirs,” Prine reminisces about various keepsakes and mementos that evoke memories of past relationships and experiences. Each verse describes a different object—a postcard, a silver locket, a faded photograph—and the memories associated with it. The song’s introspective lyrics capture the nostalgia and sentimentality that often accompany the process of reminiscing about the past.
Throughout the song, Prine reflects on the transient nature of life and the inevitability of change, as he sings, “All the snow has turned to water / Christmas days have come and gone / Broken toys and faded colors / Are all that’s left to linger on.”
“Souvenirs” is a beautifully crafted song that showcases Prine’s ability to evoke deep emotions and capture the complexities of human experience through his lyrics and music.
9. All the Best
“All the Best” is a heartfelt song written by John Prine, featured on his 1991 album “The Missing Years.” The song is a warm and sincere farewell message, often interpreted as Prine bidding goodbye to a loved one or friend.
In “All the Best,” Prine expresses his wishes for someone’s well-being and happiness, acknowledging that they may be going through a difficult time or embarking on a new journey. The lyrics convey a sense of gratitude and fondness for the person, as Prine sings lines such as “I wish you love and happiness / I guess I wish you all the best.”
The song’s gentle melody and sincere lyrics resonate with listeners, evoking feelings of empathy and understanding. “All the Best” has become one of John Prine’s signature songs, cherished for its heartfelt sentiment and universal message of goodwill.
10. Illegal Smile
“Illegal Smile” is a song written and performed by John Prine, featured on his self-titled debut album released in 1971. The song is known for its humorous yet thought-provoking lyrics, and it has become one of Prine’s signature songs over the years.
The lyrics of “Illegal Smile” playfully explore the concept of finding joy and solace in the midst of life’s challenges, often through the use of humor or a carefree attitude. The titular “illegal smile” refers to the act of smiling in defiance or in disregard of societal norms or expectations.
The song’s catchy melody and clever wordplay have made it a favorite among fans of folk and Americana music. It’s a testament to Prine’s ability to combine wit, insight, and melody into a memorable and timeless song.