Top 10 Most Beautiful Songs by Paul Simon

After the unprecedented success of Simon & Garfunkel, Paul Simon proved as a solo artist to be one of the most innovative, intellectual and curious songwriters of the twentieth century. Armed with razor-sharp poetic lyrics and an insatiable urge to fuse Western pop with South African mbaqanga, Brazilian percussion and gospel, the New Yorker created a body of work of unprecedented artistic height. Vote for your favorite Paul Simon song.

Posted by Sophie · 9 votes · August 10, 2026

Cast your vote - the ranking shifts live based on the votes.

#1

You Can Call Me Al

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His biggest worldwide pop monument. The blazing horn riff, that legendary bass run and Simon's witty existential lyrics about a midlife crisis abroad, combined with the hilarious video starring Chevy Chase, make this an indestructible classic.

#2

Graceland

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The enchanting title track of his groundbreaking album. Floating on Bakithi Kumalo's supple fretless bassline, Simon sings about a spiritual pilgrimage to Elvis' estate after the collapse of his marriage; a literary masterpiece of comfort and reconciliation.

#3

50 Ways to Leave Your Lover

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Immortalized by Steve Gadd's iconic, military-precise drum pattern. Simon combines a melancholy ballad about relationship doubts with a bone-dry, rhyming chorus full of practical escape routes ('Just slip out the back, Jack').

#4

Me and Julio Down by the Schoolyard

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An irresistibly swinging pop song full of mysterious street humor. Driven by a catchy cuíca percussion sound and virtuoso acoustic guitar playing, Simon sings about an unspecified prank in the schoolyard.

#5

The Obvious Child

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The masterful opener of The Rhythm of the Saints, driven by the thundering percussion of the Brazilian drum group Olodum. A layered reflection on the relentless passage of time.

#6

Diamonds on the Soles of Her Shoes

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Opened by the breathtaking a cappella harmonies of South Africa's Ladysmith Black Mambazo, the song then turns into a festive, danceable mbaqanga groove about a rich woman and a poor boy.

#7

Late in the Evening

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An explosion of Latin jazz and salsa energy driven by virtuoso horns and Steve Gadd's masterful drumming. Simon tells vivid memories of his musical coming of age as a teenager in New York.

#8

Kodachrome

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A cheerful, sparkling ode to nostalgia and the power of memories, named after Kodak's famous color film. The rousing piano and Simon's humorous opening line make this a crowd favorite.

#9

Slip Slidin' Away

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A fragile, philosophical folk ballad about the elusiveness of happiness and how dreams can slip through our fingers. Supported by acoustic strings and the warm gospel harmonies of The Oak Ridge Boys.

#10

Mother and Child Reunion

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One of the first American pop hits to embrace authentic Jamaican reggae, recorded in Kingston. Despite the melancholy title, the song swings with a relaxed, sunny groove.

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