G&G Editors’ Picks: Favorite John Prine Songs

A sampling of tunes from the late singer’s abundant catalog

The cover of John Prine's self-titled debut album in 1971.

It’s not hard to get into John Prine. The man had a knack for capturing the human condition, and curious listeners could start virtually anywhere in his catalog and find something to hold onto—a fact well proven by the range of songs that stick out as favorites to the Garden & Gun staff. When news broke this week that the legendary songwriter had died, many of us turned to his music for comfort, and we began to gather recommendations for where new fans might begin to dive in. 

“I’m sure this one is already spoken for,” many staffers prefaced before launching into the why behind their favorite Prine number, “so just let me know if I should pick a different one. I have plenty of others.” But when not a single person chose the same favorite song, it felt like a testament to the depth of Prine’s discography. So if you’re just getting into Prine for the first time, take these suggestions as an entry point. Or find your own. Regardless of where you start, you’re likely to discover a new perspective on life and a damn good tune. 

“Day Is Done”

I love “Day Is Done” for its juxtapositions. Prine’s lyrics and tune seem so simple, recalling innocence, while simultaneously speaking about the complexity and betrayals in romantic relationships. Behind that meaning, the words paint a snapshot of the human journey to love and to live humbly, speaking like a prophecy and a testament to Prine’s own life: We shared our things and had some fun / now we’ll say goodbye and go back home when the day is done.
Caroline Sanders, Assistant Editor

“In Spite of Ourselves”

This song is a perfect example of Prine’s beautiful ability to marry truth and humor. A duet with Iris DeMent and the title track of Prine’s 1999 album—his first after a tough battle with throat cancer—it’s a song about love, acceptance, and sticking together. I think we all could use some of his optimism right now, and I hope today he’s somewhere a-sittin’ on a rainbow. —Kim Alexander, Digital Director

“Knockin’ on Your Screen Door”

Prine is a master at making all of us humans feel less alone, even though we’re weird and ornery and grumpy sometimes. And we fall in and out of love. We’re human! He is so good at writing earnestly but not too sweet. This song is a perfect, very human example: I ain’t got nobody hangin’ ’round my doorstep / Ain’t got no loose change just a-hangin’ ’round my jeans / If you see somebody, would you send ’em over my way? / I could use some help here with a can of pork and beans.CJ Lotz, Senior Editor 

“Hello in There”

Ya’ know that old trees just grow stronger / And old rivers grow wilder ev’ry day / Old people just grow lonesome  / Waiting for someone to say / “Hello in there, hello.” Prine may have written this with “old people” in mind, but who hasn’t felt a little isolated, a little forgotten? The way I hear it, “Hello in There” is asking us to keep reaching out to people with warmth and acceptance—even if they seem unreceptive, even if they’re putting on a brave face, even if it’s easier to ignore them and keep walking. The message feels more important now than ever. Then again, most of Prine’s words do. —Dacey Orr Sivewright, Digital Editor 

“It’s a Big Old Goofy World”

A song he wove out of clichéd idioms—“drinks like a fish,” “happy as a clam,” etc.—into something clever, amusing, but also really touching. Like most great songs, it transports you to a certain time in your life (in my case, to Colorado in the early ’90s, when it was getting a lot of airplay on the great Boulder FM station KBCO). Like probably everything he wrote, it stops you in your tracks and forces you to pay attention. Listening to it again right now makes me tear up, as I suspect any John Prine song will for a pretty good while now. —Mike Grudowski, Contributing Editor 

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

Prine’s 1971 self-titled debut is rightly heralded as a classic, with “Sam Stone” and “Angel from Montgomery” as the tentpoles, but the song I keep coming back to is “Your Flag Decal Won’t Get You into Heaven Anymore.” Prine is calling BS on fake patriotism and hypocrites as he sings about “your dirty little war.” With searing small-town imagery and the line “Jesus don’t like killing no matter what the reason for,” “Your Flag” has remained prescient for almost fifty years, a sad fact but also a marker of Prine’s greatness. —Matt Hendrickson, Contributing Editor

“Donald and Lydia”

Back in the fall of 2009, my friend Tom Lake, now a journalist for CNN, gathered a bunch of his friends from across the country for what would become an annual writers’ conference of sorts, one that inevitably, by the end of the night, turns into a hootenanny, with everyone passing around a guitar for a sing-a-long. That’s the first time I heard “Donald and Lydia,” a song from Prine’s 1971 debut album. Perhaps it was the journalist S.I. Rosenbaum who sang it for us; bourbon makes the memory fuzzy. But I do recall how much the lyrics delighted me, the story of two people seeking love, a song full of Prine’s signature wry humor, wistfulness, yearning, and his ability to find beauty in the smallest of moments and the unlikeliest of places. —Amanda Heckert, Deputy Editor

READ MORE: “When John Prine Gets to Heaven,” a Remembrance by John Huey