The Extraordinary And Turbulent Life Of Paul Simon

Paul Simon Is Music’s Controversial Genius
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Enigmatic Facts About Paul Simon, Music’s Controversial Genius
Jul 31
INTERESTING
A.V. Land
He Couldn’t Escape Himself
Paul Simon once sang, “I am a rock, I am an island”—and he wasn’t lying. Simon’s songwriting brilliance is as complicated as the man himself. Beneath the chart-topping, era-defining music, he was a minefield of neuroses: obsessed with control, wracked with self-doubt, and locked in one of music’s most outrageous feuds with his angel-voiced partner, Art Garfunkel.
Behind the hits lay a trail of controversy, failed love affairs, wild, substance-fueled nights with Princess Leia, and a genius who couldn’t stop unraveling.
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1. He Was Born Sad
When Paul Simon was born on October 13, 1941, he didn’t enter the world with a wail, but with a heavy sigh. His parents, Louis and Belle, peered into his crib expecting baby giggles, but instead, they were met with a furrowed brow and eyes full of existential despair. At first, they panicked. Was something wrong with their newborn?
Eventually, they just leaned into it and even nicknamed him after gloomy-faced Supreme Court Justice Benjamin Cardozo.  Simon’s lifelong aura of melancholy? Yeah, it started before he could even crawl.
Michael Putland, Getty Images
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2. He Was Small But Scary
Growing up in Queens,  New York , Simon worshipped at Yankee Stadium, while his mother did the same at the synagogue. Baseball was his first religion, and though he was athletic, he was also tiny. Still, what he lacked in size, he made up for in sheer scrappiness. When mean kids messed with him, he didn’t back down. He’d snatch his hat back and then stomp back to the classroom and ace a test.
He would soon find a far more powerful (and less painful) way to stand out…
Chris Walter, Getty Images
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3. He Discovered The Power Of “Art”
One afternoon in 1952, the school buses at Simon’s elementary school were running late— and fate stepped in. To pass the time, teachers dragged the kids to the auditorium for an impromptu talent show. A curly-haired blonde boy named Art Garfunkel took the mic. The moment he started to sing, jaws dropped.
His clear, rich voice rang out like bells, silencing the rowdy kids and leaving the girls starry-eyed.  One fourth-grader sat there soaking it all in: Paul Simon.
Eddie Mallin, Wikimedia Commons
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4. He Wanted The Spotlight—Badly
As young Simon sat in the auditorium absorbing the applause, the attention, and the magic surrounding Art Garfunkel’s performance, something clicked into place. He wanted that. He  needed  that. It wasn’t a crazy idea... Simon’s father was a bandleader when he wasn’t working as a professor, after all. Sure, Garfunkel was now known as “the most famous singer in the neighborhood,” but Simon had something else: quiet ambition.
While Garfunkel basked in the spotlight, Simon started working on his voice…and a plan.
Michael Ochs Archives, Getty Images
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5. His Father’s Words Changed Everything
Simon wasn’t just another kid with a silly daydream—he was a one-person boot camp. He’d bring a record player to his room for privacy and sing his little heart out. He was doing just that one day when his father poked his head in the door, smiled, and said, “You’ve got a nice voice”.
Coming from Louis Simon—a professional musician who rarely handed out compliments—that one sentence was like getting knighted.  He could sing.  For the first time, it felt like the pieces were falling into place.
Chris Walter, Getty Images
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6. His Life Was About To Change
Ever since Garfunkel's show-stopping school debut, Simon had been quietly admiring him from afar in the hallways and at talent shows. The two had barely spoken until, at age 12, fate cast them both in the school’s production of  Alice in Wonderland.  Fittingly, Simon was the anxious White Rabbit, and Garfunkel was the chill Cheshire Cat. They shared a sharp sense of humor and a growing obsession with music.
By the end of the play, they weren’t just friends, they were a duo—and they were already turning into local legends.
-, Getty Images
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7. He Was A Teen Idol
By high school, Simon and Garfunkel weren’t just neighbourhood heroes—they were rising stars. They spent hours face-to-face in Garfunkel's basement, obsessing over harmonies and tightening every note until it clicked. The work paid off. Their debut single, “Hey, Schoolgirl,” hit #49 on the charts under the stage names Tom & Jerry. They even scored a spot on  American Bandstand.
To the outside world, it looked like the start of something big.  But behind the scenes, the cracks were already forming.  Simon had a secret, and Garfunkel had no idea what was coming.
Michael Ochs Archives, Getty Images
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8. He Started Off On A Bad Note
While their first hit was climbing the charts, Simon forgot to mention one tiny thing to his bandmate and best friend: He’d already cut a secret solo deal behind Garfunkel’s back. While Simon and his father negotiated with the record label, they had quietly locked in a second contract for Simon  alone . His dad, dreaming of creating the next  Elvis , even wrote a goofy rockabilly track and rushed Simon into the studio to record it.
When Simon finally told Garfunkel? The betrayal hit him like a brick.
Charlie Gillett Collection, Getty Images
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9. He Broke The Rules
It’s no wonder that Simon versus Garfunkel became one of rock’s longest-running feuds. That said, the real mystery is how Garfunkel ever trusted him again. When Simon eventually told Garfunkel about the secret solo deal, he tried to downplay it as nothing. Garfunkel didn’t buy it—and neither did his furious parents.
Paul Simon and his father had lied, plain and simple. Maybe the universe agreed, because Simon’s solo single flopped  hard  while demand for Tom & Jerry kept growing.  Was that enough to smooth things over? Maybe…for now.
Hulton Archive, Getty Images
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10. He Loved The Grind
From the late 50s to  the early 60s , Simon was a music-making machine—writing, recording, and producing under a string of fake names. But no matter how far he strayed, he always circled back to Tom & Jerry, reuniting with Garfunkel when the chemistry called for it.  Then, in 1964, their big break arrived.
Clive Davis signed them to Columbia Records—and this time, they weren’t hiding behind fake names. Simon & Garfunkel were born.  It should have been a dream, but it blew up in their faces.
U.S. Department of State, Wikimedia Commons
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11. He Flew The Coop
It almost sounds like an emo album, and the sentiment is similar:  Wednesday Morning, 3 A.M.,  their official debut as Simon & Garfunkel, hit shelves in October 1964…and tanked . Simon couldn’t take it. Just like when he was being teased in the schoolyard all those years ago, he stormed off.
Only this time, he fled to England, fell headfirst into a new romance, and started building the next chapter of his legend—without Art Garfunkel.
Bettmann, Getty Images
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12. He Didn’t Exactly Charm The Brits
When Simon landed in London, he was in his early 20s and ready to soak it all…

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