Few songwriters have captured the raw beauty of human experience quite like John Prine. With a career spanning over five decades, Prine’s music is a blend of wit, wisdom, and deeply felt emotion—an unparalleled combination that has earned him a place among the most revered American songwriters. Whether he’s telling stories of love, loss, or the quirky absurdities of life, Prine’s lyrics resonate with listeners across generations. His ability to convey complex emotions in the simplest of words makes each song a timeless treasure.
In this article, we’ll take a journey through the legendary catalog of John Prine by counting down his top 10 most popular songs of all time. From poignant ballads to catchy folk tunes, these tracks have left an indelible mark on the hearts of fans and critics alike. Whether you’re a lifelong fan or discovering his music for the first time, this list will showcase the very best of Prine’s incredible gift for storytelling. So grab your headphones and get ready to immerse yourself in the world of one of America’s greatest songwriters. These are the songs that have defined John Prine’s legacy and continue to inspire generations of music lovers.
1. Angel from Montgomery (1971)
Released on his self-titled debut album in 1971, Angel from Montgomery quickly became one of John Prine’s most beloved songs. This poignant ballad tells the story of a woman stuck in the monotony of life, yearning for escape. With its vivid imagery and powerful lyrics, the song became an anthem for those aching for a sense of freedom and change. It’s often covered by other artists, most notably Bonnie Raitt, who helped elevate its status to legendary. The haunting refrain, “Make me an angel that flies from Montgomery,” is a stunning example of Prine’s ability to blend sorrow and hope into a single line, making it one of his most enduring classics.
2. Paradise (1971)
Also from his 1971 debut album, Paradise is a heartfelt tribute to the small coal mining town of Paradise, Kentucky, where Prine’s parents were raised. The song paints a vivid picture of a town ravaged by environmental destruction, specifically by the Peabody Coal Company. With its nostalgic tone and gentle melodies, it became an instant favorite among fans. It’s a beautiful reflection on the loss of natural beauty and the impact of industrialization, told with sincerity and simplicity. The song’s chorus, “Mr. Peabody’s coal train has hauled it away,” strikes a chord with anyone who has experienced the disappearance of a beloved place.
3. Hello in There (1971)
Hello in There is one of Prine’s most emotionally affecting songs, dealing with the loneliness of old age. Released in 1971, this ballad finds Prine stepping into the shoes of an elderly person, reflecting on the alienation and isolation that can come with growing old. With its delicate, heartfelt lyrics, Hello in There invites listeners to take a moment and acknowledge the lives and stories of the elderly. The line, “We lost Davy in the Korean War, and I still don’t know what for,” is a masterclass in Prine’s ability to tell entire stories with just a few words.
4. Sam Stone (1971)
One of Prine’s most iconic and tragic songs, Sam Stone tells the story of a Vietnam War veteran who returns home only to succumb to substance abuse. Released in 1971, the song’s unflinching portrayal of a soldier’s post-war struggles resonated deeply with listeners, especially during the Vietnam era. The refrain, “There’s a hole in Daddy’s arm where all the money goes,” is one of the most chilling lines in his entire catalog, perfectly capturing the despair of addiction. Prine’s empathy and storytelling in this track cemented his place as a socially conscious songwriter with a deep sensitivity for human suffering.
5. In Spite of Ourselves (1999)
Released as the title track of Prine’s 1999 album, In Spite of Ourselves is a delightful duet with Iris DeMent. This humorous and heartwarming song celebrates the quirks and imperfections of a long-term relationship. The playful back-and-forth between Prine and DeMent creates a charming chemistry that listeners can’t help but love. With lines like, “He ain’t got laid in a month of Sundays, I caught him once and he was sniffin’ my undies,” the song’s self-deprecating humor shines through. It’s a testament to Prine’s versatility as a songwriter, showing that he could master both the heartbreaking and the hilarious.
6. Illegal Smile (1971)
Illegal Smile opens Prine’s debut album with a lighthearted take on the joys of escaping reality, widely interpreted as an ode to marijuana use. However, Prine himself has said that the song is more about finding peace in the little things in life. Released in 1971, its upbeat tempo and playful lyrics instantly endeared it to fans. The tongue-in-cheek delivery of lines like, “Well done, hot dog bun, my sister’s a nun,” showcase Prine’s clever sense of humor. It’s a song that reminds listeners to find their own version of happiness, whatever form that may take.
7. Lake Marie (1995)
From Prine’s 1995 album Lost Dogs and Mixed Blessings, Lake Marie is a uniquely structured song that blends poetic storytelling with a haunting melody. It tells two parallel stories: one of a failing relationship and another of a Native American legend surrounding Lake Marie. The song’s chorus, “We were standing, standing by peaceful waters,” contrasts with the darker, more mysterious verses, creating a hypnotic tension. Prine’s ability to weave together personal and mythical narratives makes Lake Marie one of his most ambitious and critically acclaimed songs.
8. That’s the Way the World Goes ‘Round (1978)
Released in 1978 on the album Bruised Orange, That’s the Way the World Goes ‘Round is a witty, upbeat tune that looks at life’s ups and downs with a sense of humor. Prine sings about a man who’s down on his luck, but the song’s infectious rhythm and optimistic lyrics remind listeners to keep going despite life’s setbacks. With its catchy chorus and whimsical storytelling, it’s a fan favorite and a perfect example of Prine’s talent for turning life’s struggles into something to smile about.
9. Speed of the Sound of Loneliness (1986)
Released in 1986 on the album German Afternoons, Speed of the Sound of Loneliness is a haunting ballad about the emotional distance that can grow between two people. The melancholy melody perfectly complements the song’s theme of loneliness and heartache. Prine’s voice, weary yet full of emotion, brings the lyrics to life, making it one of his most affecting songs. This track has been covered by numerous artists, further cementing its place as one of his most enduring contributions to American music.
10. Clay Pigeons (2005)
Clay Pigeons is a cover of Blaze Foley’s song, released by Prine in 2005 on his album Fair & Square. Prine’s rendition of this melancholic tune about starting over and finding solace in the simplicity of life brings a new level of warmth and depth to the original. His weathered voice adds a unique emotional weight to lines like, “I’m going down to the Greyhound station, gonna get a ticket to ride.” The song’s themes of redemption and self-reflection make it a fitting addition to Prine’s catalog, and it became a fan favorite soon after its release.