Paul Simon has sold more than 50 million albums. He’s been inducted into the Rock and Roll Hall of Fame twice. He’s won 12 Grammy Awards, an Oscar, the Gershwin Prize for Popular Song and been recognized as a Kennedy Center Honoree.

Trying to sum up his career in only six songs seems impossible, but otherwise we’d be writing forever. Let’s start from the beginning…

“America” (1968)

From “Mrs. Robinson” to “Bridge Over Troubled Water”, Paul Simon wrote a staggering number of modern standards during his partnership with Art Garfunkel. However, few of them hit quite as hard as “America.” Originally released on their classic album Bookends, it’s a story about young lovers on a road trip that starts off fun and devolves into existential dread.

“Me and Julio Down by the Schoolyard” (1972)

No one’s really sure what “The Mama Pajama” saw in this song - not even Paul Simon himself. Fortunately, you don’t need to understand the lyrics to enjoy a song like “Me and Julio Down by the Schoolyard.”

“50 Ways to Leave Your Lover” (1975)

The second single from his classic LP Still Crazy After All These Years, “50 Ways to Leave Your Lover” sounds just as fresh as anything released in 2019. Built around a jazzy snare riff, the song snaps into an earworm of a chorus that’s unmistakably Paul Simon. (That must explain how it ended up being his first #1 hit as a solo artist.)

“René and Georgette Magritte with Their Dog After the War” (1983)

Inspired by a photo he found at Joan Baez’s home, Paul’s lyrics practically paint a picture of their own, portraying the iconic surrealist artist as a secret fan of 1950s doo-wop groups like The Penguins and The Five Satins. Last year, he teamed up with yMusic to revisit the song with a brand new arrangement for his album In The Blue Light.

“Diamonds on the Soles of Her Shoes”(1986)

In a career full of classic albums, Graceland was a life-changing release for Paul Simon. Not because it sold 15 million copies and won the 1986 Grammy Award for Album of the Year, but because of the cultural impact it made by featuring collaborations with South African artists during the era of apartheid. With contributions by Ladysmith Black Mambazo and Youssou N’Dour, “Diamonds on the Soles of Her Shoes” is more than just another catchy pop song. It’s the sound of musicians coming together in a universal language to break down barriers.

“The Obvious Child” (1990)

After the critical and commercial success of Graceland, Paul found inspiration by collaborating with Brazilian musicians on 1990’s The Rhythm of the Saints. The album opens with “The Obvious Child”, a song they recorded live on the streets of Salvador’s Pelourinho Square. Featuring urgent percussion from the Olodum drum collective, it combines his lifelong love of 1950s rock ‘n’ roll with traditional Latin American rhythms to create a sound unlike anything you’ve heard before. If anyone was skeptical of this musical melting pot, Paul explained it all - “The ear is willing to accept it when the rhythm is right.’’