Our 10 Favorite John Prine Songs

There’s little that can be written about John Prine that hasn’t already been said. Here are some lines just from the obituaries published in the last 15 hours: His songs “saw the whole of us,” he “chronicled the human condition,” he was an “Americana legend” known for “wit and warmth.” You won’t find many who disagree with those assessments. It’s a word we shouldn’t be too comfortable flinging around, but Prine was and will remain a legend. He was revered by musicians in the same way that Bob Dylan, Leonard Cohen and Joni Mitchell are—almost universally. He was prolific in the truest sense of the word, and like that one headline reads, he had ways of reporting on the human condition that were entirely unique to him. It’s all been said, but, thankfully, his songs beg listen upon listen, offering up new meaning with time and age. So, as he would have been wont to do, I’ll keep this short and to the point: John Prine was one of the best we ever had. His music will live on in our hearts forever. Here are 10 of the many wonderful, wise tunes he gave us while we had him.

1. “Angel From Montgomery”

You won’t find very many 25-year-old male musicians writing from the perspective of an older woman, but John Prine had a gift for storytelling that knew no bounds. Singing with beautifully grizzled vocals over rousing organs, Prine pleads with angels on “Angel From Montgomery” to be saved from a loveless marriage, lost dreams and a life devoid of purpose. Various covers of this song by John Denver, Bonnie Raitt and Tanya Tucker helped popularize the song, and Raitt’s version, in particular, is an absolute knockout. —Lizzie Manno

2. “Clay Pigeons”

Some answers are out there waiting for you somewhere. Others are already inside you, waiting for you to discover yourself. Prine contemplates the logistics of those questions on his appropriately harmonica-heavy (it’s the instrument of the road, after all) interpretation of Blaze Foley’s “Clay Pigeons.” “I’m tired of runnin’ ‘round / Lookin’ for answers to questions that I already know,” he sings. The prevailing theme of loneliness is found between the lines, as with many of his great songs. —Ellen Johnson

3. “Fish and Whistle”

Maybe you’ve never heard a John Prine song in your life. But if someone spun his 1978 album Bruised Orange for you, unprimed and unprepared, my bet is you’d be smitten within the first few seconds of that record’s first song, the jaunty “Fish and Whistle.” To the tune of one especially chirpy flute, Prine sings, “We’ll forgive each other ‘til we both turn blue.” It doesn’t matter how much beautiful nonsense he crams into his folk songs, John Prine always leaves a nugget of wisdom. Isn’t that a beautiful idea, that we’ll all just keep forgiving each other as long as we live, because that’s part of being a human? End your feuds; do it for John. —Ellen Johnson

4. “Hello in There”

“Hello in There” is the spirit of country music in a nutshell. Prine has always been capable of reaching out his hand and pulling people out of the dumps, but he really sounds like he’s sharing memories with listeners one-on-one on his front porch with this song. Whether it’s John and Linda in Omaha, Rudy at the factory or Davy from the war, we get an insight into the blood, sweat and tears of America. It’s a reminder that we’re not alone in our personal or existential struggles, and the best way to get out of it is to bond over our struggles with others, especially when they might be in a far deeper (or invisible) hole than us. The song feels like such a big entity, even separated from his masterful 1971 debut album. —Lizzie Manno

5. “Illegal Smile”

Who else besides John Prine could have the wit and wherewithal to sing the line, “A bowl of oatmeal tried to stare me down, and won?” It’s clever in the dryest way possible. But, you see, Prine’s assessment of determined inanimate objects isn’t the only reason songs like this succeed: It’s his broader interpretations of life, set to the bumbling honky-tonk guitars and sung in that charcoal rasp. It’s “the key to escape reality” that he so uniquely describes, the attitude you need not only to survive life’s many turmoils, but to dance around them laughing. —Ellen Johnson

6. “Sam Stone”

There are few lyrics as sobering as this one from John Prine’s “Sam Stone”: “There’s a hole in daddy’s arm, where all the money goes.” Taken from his 1971 self-titled debut album, this acoustic song lays bare the horrors of war long after combat has ceased. The protagonist succumbs to a drug addiction after his severe wartime injuries, and his children’s innocent, simplistic view of their father’s darkest demon just hits you like a barreling train. Speaking of which, there’s another powerful, slightly more vivid allusion to locomotives when Prine describes the center of his main character’s universe, the rush you get from taking heroin: “And the gold rolled through his veins / Like a thousand railroad trains.” —Lizzie Manno

7. “Summer’s End”

Not many artists can say they wrote some of their best songs in the last three years of their career. But John Prine, as it is abundantly clear, wasn’t most artists. He captured an overwhelming sadness seasoned with hope in his 2018 song Summer’s End, from The Tree of Forgiveness, his last album. The lyric sheet could read like a musing on death, an invitation from an estranged family member to mend broken ties, a note from a longtime lover or partner post-conflict, or, if you’re of the spiritual type, even the call to return to one’s rightful home with God. “Come on home,” he sings over and over. “The moon and stars hang out in bars just talking,” Prine adds. “I still love that picture of us walking.” It’s not flashy, but it’s beautiful, and leaves the door wide open for a listener’s interpretations. —Ellen Johnson

8. “Sweet Revenge”

The title track from John Prine’s 1973 album, Sweet Revenge, showcases just how colorful and playful his songwriting could be. He opens the song with a witty biblical reference—“Got kicked off Noah’s Ark / I turn my cheek to unkind remarks”—and fills it out with tales of a milkman, English teacher and local DJ. It’s also one of Prine’s best singalongs and most satisfying fusions of bluesy heartland rock and pining, gruff folk. —Lizzie Manno

9. “That’s the Way the World Goes Round”

John Prine managed to channel an unwavering hope in a way that doesn’t sound trite or tone deaf. He sees the good in people in a way that might enrage others, but ultimately Prine always brings us back to our common humanity via stories of the everyday man. On paper, an acoustic-based song called “That’s the Way the World Goes Round” with a prominent perky recorder fluttering in the background sounds like something out of VeggieTales, but Prine taps into a deeply-felt poignancy—and so much so that it would bring any grown adult to tears in the right circumstances. —Lizzie Manno

10. “Your Flag Decal Won’t Get You into Heaven Anymore”

In Roger Ebert’s review of an intimate John Prine set in 1970 (the first official review of Prine’s music, according to Rogerebert.com), the critic notes lyrics from this song right away: “Your flag decal won’t get you into heaven anymore; It’s already overcrowded from your dirty little war.” This song has plenty of meaning in its relation to the Vietnam War, but, as you can imagine, it still feels especially pertinent today. “Now Jesus don’t like killin’, no matter what the reason’s for.” Patriotism won’t get you extra points with the man upstairs, but pacifism just might, at least per John’s reasoning. It’s a song about peace, and we can never have too many of those. Prine always had a way of making the chaotic calm and the overwhelming digestible. This time, he did it with a not-so-subtle swatch of protest. —Ellen Johnson