John Prine didn’t write songs so much as he captured the stuff we usually ignore—the dust on a screen door, the silence in a kitchen, or the way an old person looks when they think nobody’s watching. If you’re hunting for a john prine song list, you’re probably looking for more than just a chronological discography. You want the heart. You want the reason why Dylan called him "Midwestern mind-trip" and why every Nashville songwriter worth their salt tries to steal his phrasing.
Most people start with the hits. That makes sense. But Prine’s catalog is a weird, beautiful thicket. It’s got goofy songs about space aliens and devastatingly quiet songs about loneliness that feel like a punch to the solar plexus.
The "Big Three" Every John Prine Song List Needs
You can't talk about Prine without the 1971 self-titled debut. Honestly, it’s a bit unfair to every other songwriter that he came out of the gate with this record. He was a mailman in Chicago, just finishing his route and writing masterpieces in his head.
"Sam Stone" is usually the first one people mention. It’s a brutal look at a veteran coming home with a "purple heart and a monkey on his back." It doesn’t judge. It just observes. Then you have "Hello in There," which is basically a manual on how to be a decent human being to the elderly. Prine wrote it when he was in his early twenties, which is frankly insane. How does a kid know how it feels to be an old man named John with a wife named Elsie?
Then there's "Angel from Montgomery." Bonnie Raitt made it world-famous, but hearing John sing it—the guy who actually wrote those lines about wanting to be an angel—gives it this gritty, grounded reality. It’s a song about a middle-aged woman stuck in a marriage that’s just "burnt-out charcoal."
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The Songs That Make You Laugh (Because You Have To)
Prine wasn't all gloom. Not even close. He was hilarious. He had this way of looking at the world that was slightly tilted. Take "Dear Abby." It’s literally a series of letters to an advice columnist. The punchline? "You have no complaint / You are what you are and you ain't what you ain't."
It’s simple. It’s catchy. It’s the kind of song you sing at a campfire when everyone’s had a few beers.
Then you’ve got "Illegal Smile." People thought it was a drug song for years. John always said it was just about having a private joke with yourself when the world gets too heavy. "In Spite of Ourselves" is another essential. It’s a duet, usually performed with Iris DeMent, and it’s arguably the most honest song about a long-term relationship ever written. It mentions "sniffing undies" and "big ol' hearts." It’s messy. It’s real.
Middle-Era Gems You Might've Missed
The 80s were weird for everyone, and Prine wasn't immune. He started his own label, Oh Boy Records, because he was tired of the industry nonsense. This is where he found his true voice.
- "Souvenirs" — A reflection on how we try to hold onto the past with cheap trinkets.
- "Fish and Whistle" — A bouncy tune about forgiveness and just getting through the day.
- "Speed of the Sound of Loneliness" — This one is a masterclass in songwriting. It asks, "How can a love that seems so right turn into a song about the speed of the sound of loneliness?"
There's a specific texture to these recordings. His voice started to get a bit gravelly. He survived squamous cell carcinoma in the late 90s, which changed his voice significantly. It became deeper, more resonant, and—if possible—even more empathetic.
The Late-Career Masterpieces
When John Prine released The Tree of Forgiveness in 2018, nobody knew it would be his final studio album. It felt like a victory lap. "When I Get to Heaven" is the closer, and it’s basically his manifesto for the afterlife. He talks about smoking a cigarette that’s nine miles long and opening a nightclub called "The Tree of Forgiveness."
"Summer's End" is the one that breaks most people. The music video, directed by Kerrin Sheldon and Elaine McMillion Sheldon, focuses on the opioid crisis, but the song itself is a broader plea for someone to "come on home." It’s sparse. The guitar feels like it’s weeping.
Why a John Prine Song List is Hard to Rank
Ranking these songs is a fool's errand. A john prine song list changes based on your mood. If you’re feeling cynical, you put on "Your Flag Decal Won't Get You Into Heaven Anymore." If you’re feeling romantic in a "we’re both a little broken" kind of way, you play "Far From Me."
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Critics like Robert Hilburn or Greil Marcus have spent decades trying to dissect why Prine's lyrics work. They usually land on his "plainspokenness." He didn't use big words to sound smart. He used small words to tell big truths.
Essential Deep Cuts for the Real Fans
- "Lake Marie" — Bob Dylan called this one of his favorites. It’s a weird, rambling story about a murder, a crumbling marriage, and a body of water on the Illinois-Wisconsin border.
- "Mexican Home" — A heavy, humid song about his father. The imagery of the "heat lightning" is incredible.
- "Six O'Clock News" — A heartbreaking story about a kid discovering a family secret. The ending is abrupt and haunting.
- "That’s the Way That the World Goes 'Round" — Famously introduced with a story about a fan who thought the lyrics were about a "happy enchilada" instead of a "half an inch of water."
The Practical Legacy of the Mailman
John Prine passed away in April 2020 from COVID-19 complications. The world felt a little emptier after that. But the beauty of his work is that it’s durable. These songs don't date. A song about a lonely veteran from 1971 feels just as relevant in 2026.
If you're building your own playlist, don't just stick to the Spotify "This Is John Prine" list. Dig into the live albums. John Prine Live (1988) is perhaps the best way to experience him because you get the stories. His "banter" wasn't filler; it was part of the art. He’d spend five minutes telling a story about a dead dog or a locker room just to set up a three-minute song.
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The nuanced reality of Prine is that he wasn't a protest singer, though he wrote protest songs. He wasn't a country singer, though he lived in Nashville. He was a chronicler.
How to Digest This Catalog
Don't rush it. Take the first album and sit with it for a week. Then jump to Diamonds in the Rough. Skip around. Find the versions of songs he did with Bonnie Raitt, Emmylou Harris, and Kacey Musgraves.
The goal of a john prine song list isn't to check boxes. It's to find the song that makes you feel like someone finally understands that weird, specific ache in your chest.
Actionable Next Steps for New Listeners
- Listen to "The Missing Years" in full. It's the 1991 album that won him a Grammy and proved he could still dominate after a decade of being an "underground" favorite.
- Watch the "Summer's End" music video. It provides a modern context to his timeless empathy.
- Read the lyrics without the music. Prine is one of the few songwriters whose work holds up as pure poetry on the page.
- Track down the "Sessions from West 54th" performance. It’s John at his peak—funny, poignant, and vocally soulful.
- Check out the "Broken Hearts and Dirty Windows" tribute albums. Hearing artists like Brandi Carlile or Sturgill Simpson cover him shows just how influential his "simple" melodies actually are.