John Prine live in concert at Webster Hall on June 23, 2019 in New York City.
Photo by Debra L Rothenberg/Getty Images

12 Classic Songs from the Whimsical, Wonderful World of John Prine

From his time as a promising writer in Chicago's late-'60s folk scene to his role as a guiding creative light for Miranda Lambert, Jason Isbell, Amanda Shires and other modern country and Americana stars, the late singer-songwriter John Prine crafted memorable songs from both real-life emotions and surrealistic dreams.

From political commentary to tales of regular people's struggles, Prine proved time and time again to be one of the greatest wordsmiths in any genre. His way with words and takes on the human condition endeared him to students of roots music and Nashville's jet set.

That's why Prine shared stages with artists ranging from like-minded folk songwriter John Moreland to "Burn One with John Prine" singer Kacey Musgraves without ever seeming out of place. Before that, he earned praise as a songwriter from the likes of Johnny Cash and Kris Kristofferson.

The following 12 songs pretty much sum up his career, although there are way more great songs in a repertoire that remained consistently strong for nearly 50 years. It's impossible to not skip worthy picks when approaching an artist known more for solid albums than hit singles. Indeed, there are plenty more classics to pick from such stacked projects as German Afternoons, Storm Windows, Fair & Square, Common Sense, The Tree of Forgiveness, Aimless Love and Lost Dogs + Mixed Blessings.

Think of this playlist as an entry point to an American treasure and winner of the Grammy's Lifetime Achievement Award.

12. "Sabu Visits the Twin Cities Alone"

Some of Prine's best songs put listeners in the main character's shoes. In this instance from his Bruised Orange album, the character is a young, culture-shocked actor from India.

11. "Grandpa Was a Carpenter"

Only Guy Clark's "Desperados Waiting For a Train" did a better job at painting a vivid picture of a hardened, quirky and lovable old grandfather that's relatable to every youngster with an elderly role model.

10. "Spanish Pipedream"

Prine's more country-sounding material from his early years would've made amazing Nitty Gritty Dirt Band songs, as demonstrated by this slice of down-home surrealism.

9. "Bear Creek Blues"

It almost seems wrong to include a cover among a brilliant songwriter's best songs, but few have done a better job adding a shiny new coat of paint to a Carter Family original.

8. "The Late John Garfield Blues"

From Prine's nasal delivery to his memorable turns of phrase, it's probably way too easy to liken this and a few other songs to Bob Dylan during his Nashville period.

7. "Sweet Revenge"

This mix of country, blues and old-time gospel that might've made the Rolling Stones themselves green with envy remains the best title track from a Prine album.

6. "Your Flag Decal Won't Get You Into Heaven Anymore"

This one has it all: snarkiness, social commentary, dark humor and heaps of gospel and country music influence. Few could emote all of that at once in a song that's equally humorous and defiant.

5. "Hello in There"

In his mid-twenties, Prine wrote an incredibly poignant song about silver-haired daddies growing older and lonelier. It drives home the idea that a simple hello can mean the world to a stranger.

4. "In Spite of Ourselves" feat. Iris DeMent

Razor-sharp wit and uncouth wordplay plus the ideal duet partner in Iris DeMent equaled a career-defining moment as Prine wrapped up his 20th century output with the title track of a collaborative album co-starring Trisha Yearwood, Patty Loveless and Connie Smith.

3. "Souvenirs"

It'd be no easier to narrow down Prine's greatness to 12 songs if you limited your options to the songs on his first album and its follow-up, 1972's Diamonds in the Rough. The latter brought us a master class in poetic lyricism ("broken hearts and dirty windows/make life difficult to see") that exalts positive memories as something more valuable than earthly riches.

2. "Angel From Montgomery"

One of Prine's best-known songs and a highlight of his self-titled debut album, "Angel From Montgomery" beckoned his arrival as a neo-folk master songwriter before catapulting the career rise of Bonnie Raitt.

1. "Sam Stone"

Originally titled "Great Society Conflict Veteran," Prine's tale of a drug-addled Vietnam survivor's late-life struggles and premature death remains one of the most biting pieces of social commentary from a politically-contentious time.

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Honorable mention John Prine songs: "Paradise," "Illegal Smile," "Lake Marie," "That's the Way the World Goes Round," "Speed of the Sound of Loneliness," "Fish and Whistle," "All The Best," "Diamonds in the Rough," "Summer's End," "Some Humans Ain't Human," "Far From Me," "When I Get to Heaven," "Christmas in Prison," "Unwed Fathers," "Mexican Home," "Jesus, the Missing Years," "Clocks and Spoons" and a Steve Goodman co-write made famous by David Allan Coe, "You Never Even Called Me By My Name"

This post was originally published on February 14, 2018. It was expanded on Aug. 6, 2022.