5 Deep Cuts From Paul Simon That You Should Be Listening To

Paul Simon is one of those songwriters that has found cross-generational appeal and garnered respect that few wordsmiths can claim. “Me and Julio Down by the Schoolyard.” “50 Ways To Leave Your Lover.” These are songs that are, at the same time, deeply evocative of their era but still continue to inspire today.

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That vein doesn’t stop with Simon’s singles though. He has a wealth of content waiting beyond his top hits that are equally as moving. Below, we’re going through 5 of these such songs that you should add to your playlist when you’re in the mood for a little revamp.

1. “Duncan”

In this haunting vignette, Simon tells the story of a vagrant who finds himself in a New England motel and listens in on the couple arguing next door. Few artists can capture a moment in a bottle quite like Simon. Though the premise of Lincoln Duncan’s story isn’t anything too terribly lofty, the way Simon waxes poetic about meeting a girl, falling in love, and losing his innocence is something of a marvel.

2. “Something So Right”

From There Goes Rhymin’ Simon comes this jazz-flavored ballad. “Something So Right” sees Simon reckon with the hurdles he had to overcome to get to a love interest. When something goes right / Oh it’s likely to lose me / It’s apt to confuse me / It’s such an unusual sight, he sings. His past relationships have been so catastrophic that finally finding something good seems a completely foreign concept— we’ve all been there a time or two.

3. “Rene and Georgette Magritte With Their Dog After the War”

René Magritte and his wife Georgette have two famed photographs floating around in the ether from German photographer Lothar Wolleh—”René and Georgette Magritte With Their Dog During the War” and “René and Georgette Magritte With Their Dog.” Simon created an homage to these photos with this track. It’s a quaint diddy about the mid-century and it’s a folk gem to boot.

4. “The Cool, Cool River”

Taken from his 8th studio album, “The Cool, Cool River” sees Simon reflect on how we, as humans, often don’t reach our potential. He sings, Yes boss, the government handshake / Yes boss, the crusher of language / Yes boss, Mr. Stillwater / The face at the edge of the banquet. He brought this track out while on tour with Bob Dylan in the summer of 1999 and has revisited it a handful of times since.

5. “Obvious Child”

Simon took a four-year break after Graceland—a daunting album to follow up. When he finally did make his return it was with Rhythm of the Saints, which opens with “The Obvious Child.” With a sprawling percussive intro and a shuffling groove, it is a deeply underrated gem from Simon.

(Photo by Keystone/Getty Images)

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