The 10 Best John Prine Songs, Ranked

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From his time as a promising writer in Chicago's late-'60s folk scene to his current role as a creative inspiration for Miranda Lambert and other modern country musicians, John Prine has crafted memorable songs from both real-life emotions and surrealistic dreams.

Through tales of regular people's struggles and society's shortcomings, Prine proves time and time again to be one of the greatest living wordsmiths. He can really say something while being clever enough to earn such beautifully absurd song titles as "Christmas in Prison," "Jesus The Missing Years," "It's a Big Old Goofy World," "Linda Goes to Mars," "Often is a Word I Seldom Use" and the best roots music song about the Soviet Union, "Space Monkey."

The following 10 John Prine songs pretty much sum up his ongoing career. Of course, there's way more great songs in a repertoire that's remained consistently strong for going on 50 years. It's impossible to not skip worthy picks when approaching an artist known more for solid albums than hit singles. Notice there's nothing from the German Afternoons, Storm Windows, Common Sense or Lost Dogs + Mixed Blessings albums, just to name four. Still, these picks are a good entry point for a stacked back catalog.

10. "Sabu Visits the Twin Cities Alone"

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

9. "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 who's relatable to every young boy with an elderly role model.

8. "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.

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. "Bear Creek Blues"

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

5. "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's Nashville period.

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

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

3. "Angel From Montgomery"

One of Prine's best-known songs beckoned his arrival as a neo-folk master songwriter before going on to help define the career rise of Bonnie Raitt.

2. "Hello in There"

In his mid-20s, 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.

1. "Sam Stone"

Originally titled "Great Society Conflict Veteran," Prine's tale of a drug-addled Vietnam veteran'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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The 10 Best John Prine Songs, Ranked