5 Deep Cuts From John Prine That Should Have Been Singles

For a man who sang an awful lot about dying while he was still alive, John Prine’s death still came as a major shock to his fans back in 2020.

From moments like “Please Don’t Bury Me,” where he asks to be split up and taken across America for one last hurrah or starting a rock n’ roll band at the pearly gates in “When I Get to Heaven,” Prine filled his songs to the brim with his trademark humor and humanity that made taking on the world a little less daunting.

His albums are chock full of hard truths that are made a little bit sweeter with his unparalleled humor, creating countless timeless classics. With so much great material to work with, some of his other tracks might get overlooked. We’re here to give your 5 deep-cut Prine tracks that deserve their flowers.

1. “Donald and Lydia” (From John Prine, 1971)

This track sees Prine doing what he does best—telling a story. The old adage that country music is simply “three chords and the truth” has never been a better fit than with Prine’s music. Boiling weighty concepts down to bit-sized morsels is classic Prine and “Donald and Lydia” is no exception.

He paints a portrait of two lonely characters who somehow find love with one another across the song’s verses. Lydia, a girl who spends her weekends alone in her room, takes solace in Donald, a young PFC. The chorus is deeply relatable to anyone who has ever been in love as he sings, dreaming just comes natural…like the love hidden deep in your heart.

3. “The Great Compromise” (From Diamonds in the Rough, 1972)

“The Great Compromise” is a commentary on America in the Vietnam War era done in particular Prine fashion – with deep-seated humor. In the song, he compares the country to a woman who is just a little hard to love sometimes. The lyrics touch on his own personal disillusionment with the “American Dream” after spending time in the service.

He cleverly walks the line between anti-war ideas and a relationship that has gone awry singing Many times I’d fought to protect her / But this time she was goin’ too far. It’s classic Prine tongue-in-cheek lyricism with a deeper meaning waiting on the second or third listen.

2. “Pretty Good” (From John Prine, 1971)

Again touching on some heavy stuff with characteristic levity, Prine hid this gem of a song on his self-titled debut back in 1971. In this song, he takes on apathy and the idea that everything “is just about the same.”

He uses characters to tell the story for him again (a friend in Fremont, a girl named Venus, and Molly from Arkansas) with each of them telling the folk icon that everything is simply “pretty good.” Never one to shy away from potentially contentious lyrics he sings in the last verse of the song, I heard Allah and Buddha were singing at the Savior’s feast / And up in the sky an Arabian rabbi / Fed Quaker Oats to a priest / ‘Cause actually all them gods are just about the same.

4. “Dear Abby” (From Sweet Revenge, 1973)

This track was recorded live during a gig at New York State University after a studio session didn’t pan out. It’s the spontaneity of the performance that makes this song great. The moments of fumbly-forgotten lyrics only add to the defiantly funny track.

He takes on letters written to the renowned columnist, Dear Abby, asking her for advice on a number of wonky issues like his kids all being freaks and his stomach making noises whenever he kisses. In the chorus, Abby responds with a whole lotta nothing, singing, You have no complaint / You are what you are and you ain’t what you ain’t / So listen up buster, and listen up good / Stop wishing for bad luck and knocking on wood.

5. “Quiet Man” (From John Prine, 1971)

Prine’s first album is widely regarded as one of the finest debuts ever released, with nearly every song being considered a classic. But one that is often overlooked is his ode to letting go in “Quiet Man.”

His “quiet man” walks down the highway without a care in the world asking the others to not pin their blues on him. All he wants is to enjoy the night sky with rays and beams of incredible dreams. It’s carefree folk of the highest caliber.

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