15 Best John Prine Songs That Are Awesome

Over the course of his 50 year career in music, John Prine forged an American songbook that has few parallels when it came to combining humor, poignancy, social criticism, romance, and a genuine appreciation for ordinary living. So without further ado, here are our picks for the best John Prine songs ever made.

Best John Prine Songs Ever Made

Let’s begin with the song “That’s the Way That the World Goes.”

15. That’s the Way That the World Goes (1978)

Like many of the other songs on John Prine’s fifth album Bruised Orange, “That’s the Way That the World Goes” conveys a message of acceptance in an unsettling world. The song uses examples big and small, from social inequality to broken water heaters, to illustrate the challenges that people meet day to day. 

14. All the Best (1991)

Released in 1991, John Prine’s album The Missing Years marked a return to form for the singer-songwriter after a middling 1980s. As with many of Prine’s latter-day material, “All the Best” centers around commitment to oneself and one’s craft. The song uses the difficult end of a relationship as a symbolic moment for wishing the world the best even when it feels like the wish isn’t reciprocal. 

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13. Grandpa Was a Carpenter (1973)

“Grandpa Was a Carpenter” is one of many great John Prine songs that relishes in describing an ordinary American who knows what they like and is too wild, irreverent, and stubborn to change. The song’s chorus describes a man of deeply established habits, crowning these with proclaiming that Grandpa “voted for Eisenhower/because Lincoln won the war” – a perfectly Prine metaphor for a man who takes joy in the present by worshiping the past. 

12. Fish and Whistle (1978)

John Prine struck a more conciliatory tone with society’s shortcomings on “Fish and Whistle” than he had on many of his more critical early material. The song celebrates forgiveness for common imperfections, as well as gratitude for survival and community togetherness. Like many Prine songs, there is a bittersweet undertone, as the lyrics admit that the world will always be troubled and that an idealized afterlife is the best that can be hoped for. 

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11. Summer’s End (2018)

“Summer’s End” is a highlight from John Prine’s final studio album before his death in 2020, 2018’s The Tree of Forgiveness. As one might expect from a songwriter who has weathered serious illness and knows he is in his last years, “Summer’s End” projects a sense of acceptance in the face of mortality and the end of a long ride through music history. As one might also expect from someone who had been writing about acceptance for decades, the song is deeply touching and reflective of Prine’s masterful writing talents.

10. Illegal Smile (1971)

“Illegal Smile” kicks off John Prine’s first, self-titled album on a humorous note. The song is a seemingly simple ode to the pleasures offered by illegal substances, and makes a clever point of not specifying which substance in particular the narrative is enjoying. While the song’s tone is bouncy and fun, the lyrics’ sharp, unpretentiously social commentary on taboos and civil liberties in American society foreshadow the deeper levels of cultural introspection that Prine would delve into later on the album and for the remainder of his storied career.

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9. Dear Abby (1973)

“Dear Abby” is a great example of John Prine’s talent for adopting familiar language and images from day-to-day American life to tell a nuanced and relatable story. The song humorously narrates people writing to the famous newspaper column in a state of significantly greater personal disarray and emotional distress than would be published in real life. Abby wisey replies to each with a uniform response advising each writer to calm down a bit and focus on changing their perspective. 

8. The Great Compromise (1972)

John Prine’s second album Diamonds in the Rough centered itself more on romantic ballads than socio-political criticism. “The Great Compromise” tells the yearning story of a man in love with a woman who is simply too wild and independent to be confined to a steady relationship. The title refers to the narrator’s begrudging acceptance that there is nothing he can do about his emotional attachment, in spite of the painful reality that he is only one of many men in the woman’s life. 

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7. Your Flag Decal Won’t Get You into Heaven Anymore (1971)

In contrast to the tale of empathetic tragedy Prine offered on his legendary song “Sam Stone”, “Your Flag Decal Won’t Get You Into Heaven Anymore” assumed a sardonic tone more familiar to veterans of 60s protest rock. The messaging, however, was once again layered in a manner that had previously only been matched by Bob Dylan’s most incisive moments.

“Flag Decal” took aim simultaneously at the interdependent nexus between American militarism, consumerism, and religiosity, targeting the type of person who believes that the purchase of cheap “patriotic” goods will earn them spiritual salvation in spite of their ambivalence towards moral catastrophe here on Earth. On top of all that, the lyrics are funny and the melody is contagious.

6. Clay Pigeons (2005)

John Prine’s age and weariness are deeply felt on “Clay Pigeons”, which was released on his 2005 album Fair and Square. This song showcases Prine’s continuing commitment to music and storytelling, in spite of finding few new answers to life’s biggest questions and feeling an elder statesman’s inevitable sense of exhaustion. 

5. Paradise (1971)

“Paradise” is a damning critique of both environmental devastation and the practice of wistfully pining for the good old days. In the vein of many a country, blues or folk standard, the song’s chorus begins with a melodic wish for a return to the paradise offered by peaceful countryside. This paradise only exists in memory, however. In reality, the coal industry’s extraction economy has left the land barren, all for the sake of “the progress of man.” 

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4. Sweet Revenge (1973)

“Sweet Revenge” opened John Prine’s third album with a dramatic change in mood from where he had left off. The song, which projected stubborn, embittered survivalism as friends meet early graves left and right, felt more outright angry and more personal than anything on the first album.

That said, “Sweet Revenge” also successfully held on to the everyman persona that Prine had so carefully sculpted. This song endeared Prine to his fans even more, by proving that he was still one of them even when he lost his cool.

3. In Spite of Ourselves (1999)

A duet with up-and-coming singer-songwriter Iris DeMint that was released on an album of the same name, “In Spite of Ourselves” became the most popular song of John Prine’s later years. The song celebrated an awkward and ornery couple’s charming romance in spite of their difficult personal qualities. The song is a metaphor for Prine’s enduring ability to connect with audiences while remaining genuinely himself.

2. Sam Stone (1971)

The American pop music world had not heard an anti-war song like “Sam Stone” upon its 1971 release, and some might argue that it hasn’t heard one since. A harrowing tale of one ordinary soldier’s PTSD-induced deterioration into addiction and disaffected malaise in the years following his military service, “Sam Stone” tells the story of its titular hero in a tone that seamlessly combines pity, empathy, dark humor, and bitterness.

The song’s plain-spoken lyrics, minimalist instrumental arrangement and poetically layered emotional perspective presented a stark contrast with the high-energy, rock and roll anti-war anthems that had dominated the pop music world of the late 60s. 

1. Hello in There (1971)

While John Prine is widely known for his savage criticisms of American culture, he is equally known for his sympathetic appreciation and respect for everyday people. “Hello in There” is one of his all-time best display of the latter quality. The quiet song paints the perspective of an elderly couple who have become distant from their three children for varying reasons: one has moved away in search of better opportunities, another became a drifter, and a third died on the battlefields of Korea. 

The couple is lonely, yet doesn’t seem resentful. They aren’t the type to question their own fates, but they are the sort who could use a little company, respect and sympathy. “Hello in There” recognizes our society’s isolating shortcomings, and while other Prine songs carry more resentment, this one is his best ever because it settles for the notion that if nothing else we owe each other a little effort towards connection.

Conclusion

John Prine’s songs have aged gracefully, and many of them feel more pertinent and touching than ever. This list of the best John Prine songs takes listeners on an expansive journey through some of this singular songwriter’s brightest moments, with plenty of both tears and laughter promised along the way.

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