From his time as a promising writer in Chicago's late-'60s folk scene to his role as a creative role model to Miranda Lambert and other modern country musicians, 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 through songs like "Mexican Home," "Jesus, The Missing Years," "It's a Big Old Goofy World," "Picture Show," "Unwed Fathers," "Rocky Mountain Time," "The Great Compromise," "Yes They Oughta Name A Drink After You" and the best roots music song about the Soviet Union, "Space Monkey."
Despite hailing from the folk world, the Aimless Love singer's way with words and takes on the human condition always endears him to students of roots music and Nashville's jet set. That's why Prine hit the road 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.
The following 10 John Prine 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. There are plenty more classics to pick from on German Afternoons, Storm Windows, Common Sense or the Lost Dogs + Mixed Blessings albums, to name four. Still, these picks are a good entry point to the American treasure.
10. "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.
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 that'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, but 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 during his Nashville period.
4. "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 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 in popular music.
Honorable mentions: "Paradise," "Illegal Smile," "Lake Marie," "Six O'clock News," "That's the Way the World Goes Round," "Speed of the Sound of Loneliness," "Fish and Whistle," "All The Best," "In Spite of Ourselves," "Diamonds in the Rough," "Donald & Lydia"
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This post was originally published on February 14, 2018.