He was a mailman. Seriously. Before he was the "Mark Twain of songwriting," John Prine was just a guy carrying a heavy bag through the suburbs of Chicago, dodging dogs and daydreaming. He’d deliver the mail and whistle tunes he hadn't even written down yet. It’s kinda wild to think about now, but that mundane, everyday perspective is exactly why john prine john prine songs feel like they were written specifically for you, even if you’ve never stepped foot in Illinois.
Prine didn't write about superheroes or grand, cinematic romances that don't exist in the real world. He wrote about the cracks in the linoleum. He wrote about the silence between a husband and wife at the dinner table. When he passed away in April 2020 due to complications from COVID-19, the world didn't just lose a musician; it felt like we lost a collective grandfather who knew all our secrets but loved us anyway.
The Magic of the Everyday
You’ve probably heard people call him a "songwriter's songwriter." Guys like Bob Dylan and Kris Kristofferson practically worshipped him. Dylan once said Prine’s stuff was "pure Proustian existentialism," which is a fancy way of saying the man could make a song about a literal hole in the ground feel like a Shakespearean tragedy.
Take "Hello in There." Most twenty-somethings are writing about heartbreak or partying. Prine wrote that song in his early twenties, but it sounds like it was penned by someone who had already lived eighty years. It’s a plea for people to notice the elderly. He doesn't lecture you. He just describes a couple whose kids have moved away and whose friends have died. "You know that old trees just grow stronger / And old rivers grow wilder every day / Old people just grow lonesome / Waiting for someone to say, 'Hello in there, hello.'" It’s devastating. Truly.
But then, he’d turn around and write something like "Dear Abby" or "Illegal Smile." He had this weird, wonderful ability to be hilarious and heartbreaking in the same breath. Honestly, that’s the secret sauce of john prine john prine songs. Life isn't just one thing. It's messy. It’s funny because it’s sad.
The Masterpieces You Need to Hear
If you're just diving into his catalog, it can be overwhelming. The guy released over 20 albums. Where do you even start?
Sam Stone
This is arguably one of the most brutal songs ever written about the Vietnam War. It’s not a protest song in the "marching in the streets" sense. It’s a character study. It’s about a veteran who comes home with a "shattered knee" and a heroin addiction. The chorus has that famous, haunting line: "There's a hole in daddy's arm where all the money goes / Jesus Christ died for nothin' I suppose." It’s visceral. It doesn't flinch. Roger Waters from Pink Floyd has cited this as a major influence, and you can totally hear why.
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Angel from Montgomery
Most people know the Bonnie Raitt version. It’s incredible, don't get me wrong. But hearing Prine sing it—a man in his twenties inhabiting the voice of a middle-aged woman lonely in her marriage—is something else. "How the hell can a person go to work in the morning / And come home in the evening and have nothing to say?" It’s a question that haunts a lot of households. It’s about the desire to just fly away from a life that turned out to be much smaller than you hoped.
In Spite of Ourselves
Later in his career, after surviving his first bout with cancer (squamous cell carcinoma), his voice changed. It got gravelly. Deeper. More lived-in. He did this album of duets, and the title track with Iris DeMent is basically the national anthem for quirky, realistic love. It’s about two people who are kind of a mess but perfect for each other. "He ain't got no money / Her back is kind of funny / But they're the envy of the neighbors / With their lucky quarters." It’s sweet without being sappy.
The Sound of a Rusty Gate
Let’s talk about his voice. It wasn't "good" by traditional standards. He didn't have a massive range. He wasn't doing vocal runs. But it was honest. After his neck surgery in the late 90s, he lost a chunk of his throat. He sounded like a rusty gate swinging in the wind.
Strangely? It made the songs better.
When he sang "Summer's End" on his final album, The Tree of Forgiveness, that gravelly tone added a layer of mortality that a polished singer could never replicate. You could hear the years. You could hear the cigarettes. You could hear the fact that he knew he was closer to the end than the beginning.
Why the Songwriting Community Obsesses Over Him
Nashville is full of people trying to write the next "hit." Prine never seemed to care about that. He cared about the detail.
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In "Souvenirs," he talks about "broken hearts and dirty windows." In "Far From Me," he mentions a girl "waiting for the school bus in the rain." These aren't metaphors. They are snapshots. He understood that if you describe the specific, you touch the universal.
He also wasn't afraid to be political, but he did it through empathy. "Your Flag Decal Won't Get You Into Heaven Anymore" was so biting that he actually stopped playing it for years because it felt too divisive during the Iraq War era. He didn't want to preach; he wanted to connect.
The Nashville Residency and the Oh Boy Era
In the early 80s, Prine did something kind of radical. He got tired of the major label machine and started his own label, Oh Boy Records. This was way before "indie" was a buzzword. He wanted control. He wanted to sell his records to people who actually liked them, not just chase radio play.
This move saved his career. It allowed him to age gracefully. He wasn't trying to sound like the 80s or the 90s. He just sounded like John Prine. He’d play the Ryman Auditorium in Nashville, and it felt like a family reunion. The audience wasn't just fans; they were devotees.
If you ever saw him live, you know the vibe. He’d tell a story for five minutes—usually something rambling and hilarious about a hot dog or his grandma—and then drop a song that would leave the whole room in tears. Then he'd do a little shuffle dance.
The Enduring Legacy
Why do john prine john prine songs keep showing up in movies, TV shows, and cover sets? Because they are sturdy. You can strip them down to just an acoustic guitar, or you can dress them up with a full band, and the core remains unshakable.
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Artists like Brandi Carlile, Sturgill Simpson, and Jason Isbell carry the torch now. Isbell famously said that Prine was "the best we ever had." That’s high praise in a town like Nashville where everyone is a critic.
But it’s true. Prine taught a generation of writers that you don't have to be loud to be heard. You don't have to use big words to say big things. Sometimes, you just need to talk about a "Peoria river" or a "happy enchilada."
How to Truly Appreciate John Prine
If you really want to get it, don't just put him on as background music while you're cleaning the house. Sit down.
- Listen to the 1971 self-titled debut album. It’s essentially a "Greatest Hits" record, except it was his first one. Almost every song on there is a classic.
- Watch the videos of him at the Newport Folk Festival. See the way he looks at the audience. There’s no ego there. Just a guy sharing a story.
- Read the lyrics like poetry. Seriously. Print out "Six O'Clock News" or "Lake Marie" and just read the words. The narrative structure in "Lake Marie" is basically a short story that could win a Pulitzer.
- Pay attention to the humor. Don't miss the jokes. Prine was a funny man. He knew that if you can make someone laugh, they’ll open up their heart just enough for you to slip a sad truth inside.
John Prine didn't just write songs; he built a world where it was okay to be ordinary. He validated the quiet lives. He made the mailman, the lonely housewife, and the struggling veteran feel like the protagonists of their own epics. That’s why we’re still talking about him. That’s why we’re still singing along.
The best way to honor that legacy is to keep listening. Put on Diamonds in the Rough or The Missing Years. Let the stories wash over you. There’s a lot of noise in the world right now, but Prine’s voice—gravel, grit, and all—still cuts right through it.
Actionable Ways to Explore Prine's Catalog
- For the Sad Days: Listen to "Hello in There" and "Sam Stone." Let yourself feel the weight of them.
- For the Good Days: Blast "Grandpa Was a Carpenter" or "When I Get to Heaven."
- For the Storytellers: Study "Lake Marie." Notice how he weaves three different time periods together into one emotional payoff.
- For the Guitarists: Learn the "Prine Pick." It’s a simple three-finger Travis picking style, but getting that steady alternating bass thumb is the key to his "thumpy" folk sound.
- Support Independent Music: Check out the current roster at Oh Boy Records. They still carry his spirit by supporting authentic, lyric-driven artists who don't necessarily fit the "pop" mold.