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7 Greatest Paul Simon Songs

7 Greatest Paul Simon Songs

Paul Simon’s songs have been a part of music history for the last half-century. 

Many people know him as part of the 1960’s Simon & Garfunkel duo. But for the last 50 years, he’s been a solo artist and has produced some legendary music.

Today we’re looking into some of Paul Simon’s songs to discover why he’s one of the most accomplished musicians in popular music.

Let’s dive in!

About Paul Simon

Paul Simon began his musical career in New York City when he was just 15 years old. In 1956, he started performing with Art Garfunkel, who he met in school. The duo had several hits from their five albums, including Mrs. Robinson and Bridge Over Troubled Waters.

While Simon & Garfunkel had some success, it wasn’t until they split up in 1970 that Paul Simon seemed to flourish. The first three solo albums he released between 1972 and 1975 all charted in the top 5 of the Billboard 200 chart.

In the second half of the 1970s, Simon became involved in film. He wrote music for the 1975 movie, Shampoo, featuring Warren Beatty and Goldie Hawn. Two years later, Simon was cast in Woody Allen’s 1977 film, Annie Hall.

He also wrote and starred in the 1980 feature film, One-Trick Pony. Simon’s album of the same name became the movie’s soundtrack and included his Late in the Evening hit song.


Paul Simon’s most successful album came in 1986 with the release of Graceland. He traveled to South Africa to collaborate with local musicians and record music for the album. Simon wrote most of the lyrics for the songs once he returned to America. 

With the success of Graceland also came controversy. Simon was accused of breaking the worldwide cultural boycott of South Africa’s apartheid regime when he visited there in 1985. 

The musicians Simon worked with, plus the United Nations Anti-Apartheid Committee, came to his defense. It was determined he financially supported the musicians and not the government of South Africa.

Paul Simon has released 14 solo studio albums throughout his career, many of which topped music charts. He’s also won 12 Grammy Awards and was inducted into the Rock and Roll Hall of Fame in 2001.


In 2018, Simon announced his retirement from touring, preferring to spend more time with his family. However, he does still perform live concerts occasionally.

He’s currently married to singer Edie Brickell and lives in Connecticut. 

#7 Spirit Voices

About the Song: Spirit Voices is about Simon’s personal experience with ayahuasca, a plant-based psychedelic, while traveling the Amazon.

In an interview with Billboard magazine, he said, “Ayahuasca has always been there. Nobody outside of the Amazon knew anything about it.”

Best Lyric:

Some stories are magical, meant to be sung
Songs from the mouth of the river
When the world was young
And all of these spirit voices rule the night

First Appearance: The song appears on Simon’s eighth solo album, Rhythm of the Saints, released in 1990. 

#6 50 Ways to Leave Your Lover

About the Song: You may not think a song written about divorce could be humorous, but 50 Ways proves it works. Rather than turning out a serious piece about the end of his first marriage, he decided to take a comedic approach.

Best Lyric:

You just slip out the back, Jack
Make a new plan, Stan
You don't need to be coy, Roy
Just get yourself free

First Appearance: This song first appeared on the 1975 Still Crazy After All These Years album

#5 You’re the One

About the Song: Simon wrote You’re the One from the perspective of a lover coming to a difficult realization. Sometimes, we might be the person causing the pain instead of the other partner. 

Best Lyric:

Nature gives us shapeless shapes 
Clouds and waves and flame 
But human expectation 
Is that love remains the same

First Appearance: You’re the One was released as a track on Simon’s tenth solo album of the same name in 2000. 

#4 The Boy in the Bubble

About the Song: Paul Simon traveled to South Africa in 1985 to work with musicians from local townships. This was the first song he worked on upon his arrival. 

His focus while in Africa was on recording the musical arrangement for songs on his upcoming Graceland album. Simon wrote the lyrics about the potential and challenges faced in life once he returned to America.

Best Lyric:

The way we look to a distant constellation
That's dying in a corner of the sky
These are the days of miracle and wonder
And don't cry, baby, don't cry

First Appearance: The song is the opening track on Simon’s seventh and most successful, album Graceland, released in 1986.

#3 Hearts and Bones

About the Song: Simon wrote this song as a personal account of his tumultuous relationship with actress Carrie Fisher.

The love affair lasted through 12 years of dating, marriage, divorce, then dating again, before finally ending once and for all in 1989.

Best Lyric:

Thinking back to the season before
Looking back through the cracks in the door
Two people were married
The act was outrageous
The bride was contagious

First Appearance: The song is on the album Hearts and Bones, released in 1983.

#2 Diamond on the Soles of Her Shoes

About the Song: While many of his lyrics tend to have significant meanings, this Paul Simon song isn’t necessarily one of them. Another piece composed in South Africa, the musicians and singers featured in the song are the highlight. 

Best Lyric:

People say she's crazy
She got diamonds on the soles of her shoes
Well that's one way to lose these
Walking blues
Diamonds on the soles of her shoes

First Appearance: The song was on the 1986 Graceland album.

#1 Graceland

About the Song: This is another song composed on Simon’s trip to South Africa. Once he returned to the US, Simon took a road trip from Louisiana to Graceland.

The lyrics were primarily written and inspired by that experience. 

Best Lyric:

My traveling companion is nine years old
He is the child of my first marriage
But I've reason to believe
We both will be received
In Graceland

First Appearance: This was the title track on Simon’s 1986 album of the same name.

Which Paul Simon Song is Your Favorite?

Paul Simon’s songs are full of whimsical storytelling and personal emotional experiences many of us can relate with. 

If you haven’t listened to much of his music, this list of seven songs is a great start. You’re likely to find one that speaks to you and will quickly become a favorite. Let us know which one you pick!

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