Illinois native John Prine is one of America’s most talented lyricists and admired songwriters. His gentle, acoustic-based songs have captured the hearts of countless listeners since his self-titled debut album in 1971. Though he passed away in 2020, his collection of relatable, reality-driven originals remains treasured work among genres ranging from folk and Americana to country and rock.
His music transcends both genre and location. Though he could have easily been relegated to Nashville thanks to his country-folk sound, his songs resonate with everyday working people everywhere, who turn to his words for comfort and clarity amidst life’s many highs and lows. He remained a man of the people throughout his career and never forgot his roots which were born from various odd jobs and a stint as a mailman where he garnered the nickname, “The Singing Mailman,” due to his multi-tasking as a songwriter while traveling his route.
The humble troubadour would go on to win multiple Grammys and be inducted into the Nashville Songwriters Hall of Fame. Some of the biggest musicians in America have rightfully praised him, including Bob Dylan and Tom Petty, just two of the many songwriters who have drawn heavily from Prine’s extensive and moving body of work. A genuine American music icon, we detail John Prine’s best songs with this list of Billboard hits and listener favorites.
10. Hello in There
A gentle piano intro paints a sorrowful opening to ‘Hello in There,’ a poignant song first released in 1971, and re-released on Prine’s 2000 album, Souvenirs. Written when he was only 22 years old, lyrics highlight the songwriter’s old soul. Dealing with themes of loneliness and reflection, John drew from real life experiences while writing the track. In his early days, he delivered papers to an elderly care facility, and he was always struck by patients who pretended he was a relative coming to visit when he was making his deliveries because they longed for someone to connect with. Written in honor of those lonely souls who touched him so much, ‘Hello in There’ would go on to be a pivotal part of his legacy when he passed away. Fellow songwriter Jason Isbell, who was heavily influenced by Prine, performed the ballad in honor of his late friend. The Prine family’s foundation in honor of John’s memory is also named after the tune.
Recommended: Our pick of songs that say hello (including this one).
9. Long Monday
After battling cancer and beating it, Prine wasted no time getting back into the studio to record his album, Fair & Square. One of the record’s strongest additions, ‘Long Monday,’ contains all of the singer-songwriter’s classic techniques. The acoustic country inspired track is lyrically-driven, with Prine’s voice singing as he embarks on a car ride, life weighing heavy on his mind (as it usually does in his music). The light, airy instrumentation creates a beautiful contrast as the story of a struggling relationship is told, with a lover soon leaving the protagonist (it becomes hard to tell which character Prine represents). In the scope of his powerful work, ‘Long Monday’ remains one of his enduring tales that leaves the listener intrigued and pleasantly haunted.
8. Summer’s End
A forlorn song lamenting on the passing of time took on new meaning when the music video was shot for Prine’s nostalgia-ridden tune ‘Summer’s End.’ The directors of the 2018 film Recovery Boys also directed the video to this track which debuted the same year. The film offers an eye-opening look into America’s opioid epidemic, and the directors took the same approach with Prine’s video, which he proudly approved of. The video along with the song’s poetic lyrics had a great impact on listeners and critics alike. American Songwriter magazine voted ‘Summer’s End’ as their favorite song of 2018.
7. Fish and Whistle
Prine surprisingly spent a good portion of his professional career as a mailman. As he walked his route, he would make up tunes. ‘Fish & Whistle’ is one of his fan-favorite, enduring tracks that offers a seemingly stream-of-consciousness style look into his everyday life. Delving heavily into his work life and personal life, he regales audiences about a day in the life of John Prine in his early years over country-folk style instrumentation. In true artistic fashion, it soon becomes a story with deeper meaning, highlighting life’s minute problems that can soon turn worse. When Prine first introduced the track to a live audience back in 1978, he alluded to an old prayer he couldn’t quite recall from childhood that dealt with a “fish and whistle” when you were having a case of the Mondays.
Recommended: This one appears on our list of songs with fish or fishing in the title.
6. Spanish Pipedream
“Blow up your TV, throw away your paper, go to the country, build you a home.” Prine’s down home roots are on fine display with ‘Spanish Pipedream,’ an early release from his debut album. Perhaps one of his most folksy songs recorded, the sassy, succinct tune weaves a classic tale of a soldier meeting and falling in love with a very wise dancer who offers up a few life lessons. The entire production effortlessly pays homage to the cowboy songs that shaped the early American west; songs of a genre Prine would go on to influence himself in more contemporary years. The track was a favorite of country-western singer-songwriter John Denver, who released a popular cover of it in 1971, the same year Prine debuted the original.
5. Oh Boy!
Buddy Holly is reimagined with this popular cover of the pioneering rock and roller’s celebratory ‘Oh boy!’ tune. Holly first released the romantic hit single with his band The Crickets in 1957 and it spent time in the top 10 on American charts and climbed all the way to #3 in the UK. For the special project The Crickets and Their Buddies, collaborative recordings were released with star musicians like John Prine and Eric Clapton lending their talents to classic Holly songs. The early 2000s song release is a gem, and is one of Prine’s most streamed tracks.
4. That’s the Way the World Goes ‘Round
A starry, spirited track, ‘That’s the Way the World Goes ‘Round’ is a song written for the average Joe trying to get by in a world full of ups and downs. With a philosophical undertone, Prine was inspired to write the acoustic number while lamenting on all the cynicism he saw in those around him, including himself at times. Unique lyrics are a highlight of this track, with Prine engaged in skillful wordplay that only a writer of his caliber could pull off (I know a guy that’s got a lot to lose/ He’s a pretty nice fellow, kinda confused/ Got muscles in his head, ain’t never been used/ Thinks he own half of this town). Appearing on his ‘78 Bruised Peach album, country queen Miranda Lambert eventually worked up a rendition of her own and released it on her award-winning Revolution album. In true cowgirl fashion, she transformed it into a moody, Texas anthem.
3. Clay Pigeons
Featured on his critically acclaimed Fair & Square album, which garnered a Grammy Award for Best Contemporary Folk Album, Prine’s songwriting genius uses the symbolism of a Greyhound bus as a metaphor for escaping one’s problems. An everyday scenario of hopping on a bus to get out of town takes on a deeper meaning as the story builds, with the final scenes ultimately painting a picture of quiet toughness and unassuming durability.
2. Angel from Montgomery
Easily considered to be Prine’s most famous song thanks to Bonnie Raitt’s bluesy cover of ‘Angel from Montgomery,’ the nostalgic track told from the perspective of an aging woman is one of America’s most popular and important recordings to come out of the contemporary music landscape. John was famous for easily pulling off singing from different points of view, never shying away from telling a story from the eyes of a female protagonist. With poetic and deeply tangible lyrics, the woman’s yearning for meaning in her life is brilliantly conveyed through hushed desperation and simmering courage.
Recommended: Blues slide queen Bonnie Raitt did a great cover of this track. If you’d like to hear it, head on over to our list of best Bonnie Raitt songs.
1. In Spite of Ourselves (feat. Iris DeMent)
A happy-go-lucky love song about two soulmates who are perfect for each other due to their perfectly fitting imperfections, ‘In Spite of Ourselves’ marked a significant turning point for Prine in the late ‘90s. When he stepped into the recording studio with fellow singer-songwriter Iris Dement, he had no idea if he’d be able to pull off the male vocal part for the song. He had just beaten cancer, which involved a lot of radiation on his neck, possibly heavily affecting his vocals cords. Much like the song, the story has a happy ending as well. Prine pulled off the vocal take with his usual effortless, conversational style, with one exception. He had a bit more of a smokey rasp to his pipes. The bubbly tune is the title track to his 1999 album featuring an array of duets with talented female artists.