Paul Simon was eleven years old when he watched Art Garfunkel sing at a fourth grade talent show in Queens. In that moment, something shifted inside him. Shortly after, a girl walked up to Garfunkel and told him how good he was. Simon noticed immediately. Right then, he decided that singing could get you things. Attention. Approval. Maybe even love.

However, there was a problem. Art was tall, with the voice that made people lean forward and the presence that filled a room. Paul, meanwhile, was short, dark-haired, and so small he would later play on a Queens basketball team called “Five Feet and Under.” While Art collected the applause, Paul was the kid writing the songs, doing the work, building the machinery. Yet somehow, despite all that effort, Art kept getting the standing ovations.

That imbalance would define everything. First, it fueled one of the most successful musical partnerships in American history. Then it destroyed a sixty-year friendship. And ultimately, it led a small man from a cramped apartment in Kew Gardens Hills to a thirty-acre oceanfront estate in Montauk, where the Atlantic pounds against the bluffs like it has something to prove.

Paul Simon Hamptons Roots: From a Queens Apartment to the Edge of the World

The Paul Simon Hamptons story begins three thousand miles from the ocean. He grew up in a small house on 70th Road in the Kew Gardens Hills section of Queens, surrounded by first-generation Jewish families trying to assimilate into something recognizably American. His father Louis was a jazz bassist who performed under the name “Lee Sims” because anti-Semitism in the 1940s made Jewish names professionally dangerous. Meanwhile, his mother Belle taught elementary school.

Music and baseball. Those were the pathways to belonging for kids like Paul. As Donald Fagen of Steely Dan would later describe it perfectly: “a certain kind of New York Jew, almost a stereotype really, to whom music and baseball are very important. The parents are either immigrants or first-generation Americans who felt like outsiders, and assimilation was the key thought.”

From an early age, Simon dreamed of playing for the Yankees. Every night, he oiled his glove and slept with it under his bed. Additionally, he memorized box scores and tore up Red Sox cards on principle. By high school, he was good enough to bat leadoff for Forest Hills High, even stealing home in one memorable game that made the Long Island Press. The headline read: “Simon Steals Home.”

However, there was that problem again. His size. By junior high, he knew his dream was dying. At around five feet tall, he stood far below an era when the shortest players in the majors measured five-six. Clearly, the Yankees weren’t coming. So instead, he found another way to steal the spotlight.

The Wound That Never Healed

Height became the wound that shaped everything. In his authorized biography, Simon admitted it plainly: “Being short had the most single effect on my existence, aside from my brain. It’s part of an inferior-superior syndrome. I think I have a superior brain and an inferior stature.”

To test his own pain, he created a mental game. “I’d pretend God would come to me and say, ‘If you could be six foot two with a mop of hair, would you pay a million dollars?’ I said, ‘Absolutely.’ ‘Would you pay five million?’ ‘Absolutely.’ Then the question changed: ‘Would you give away ten of your songs?’ That’s when I said no. That was too much.”

Of course, Art Garfunkel knew exactly where to cut. During a photo session when they were teenagers, something happened between them. Without warning, Garfunkel looked at his partner and said: “No matter what happens, I’ll always be taller than you.”

Unsurprisingly, Simon never forgot it. Even decades later, the memory remained fresh. “It hurt enough for me to remember sixty years later.”

Building an Empire From the Bathroom Floor

If the world wouldn’t give him height, then he would give himself something else. Control. Mastery. Essentially, the kind of power that comes from being the one who writes the songs, runs the sessions, and knows exactly how the business works.

As a teenager, he used to sing in the bathroom with the lights off, enjoying the reverb of the tiles. “Hello darkness, my old friend” wasn’t just a lyric. Instead, it was literally how he created. One night, his father came home from a gig, still wearing his tuxedo, and opened the door. “You have a nice voice,” Louis Simon said.

Remarkably, nobody had ever told him that before.

Yet it was his mother’s words that cut deeper. “You have a good voice, Paul,” Belle Simon told him once. “But Arthur has a fine voice.”

Consequently, years later, when “Bridge Over Troubled Water” earned standing ovations and everyone leaped to their feet for Garfunkel’s soaring tenor, Simon would sit at the piano thinking: “I wrote that song.”

The Partnership That Made and Unmade Them

Together, Simon and Garfunkel sold over 100 million records. Along the way, they created “The Sound of Silence,” “Mrs. Robinson,” “Bridge Over Troubled Water.” In essence, they became the Ruth and Gehrig of folk-rock, two kids from Queens hitting back-to-back home runs.

Behind the harmonies, however, the friendship was corroding. Their manager Mort Lewis saw it clearly: “They both envied the other’s place in the team. Paul often thought the audience saw Artie as the star because he was the featured singer. Meanwhile, Artie knew Paul wrote the songs and thus controlled the future of the pair.”

Eventually, when Garfunkel started taking acting roles, leaving Simon to write alone, the machinery finally broke. “He said, ‘I’ll do movies for six months, and you’ll write songs, then I’ll come back and sing for six months,'” Simon recalled. “And I thought, yeah, the hell with that.”

As a result, they split in 1970 at the peak of their fame. Subsequently, the reconciliations and fights would continue for fifty more years. Finally, in 2016, Simon said the quiet part out loud: “Quite honestly, we don’t get along. So it’s not like it’s fun.”

Paul Simon Montauk: Finding Home on the Bluffs

Somewhere in the decades between Queens and now, Paul Simon found Montauk. Notably, he didn’t choose the Hamptons proper with its hedge fund parties and see-and-be-seen restaurants. Instead, he chose Montauk. The end of the world. The place where Long Island runs out of real estate and surrenders to the Atlantic.

Today, his estate sits on Cliff Drive, encompassing thirty acres of oceanfront land overlooking the same waters that have pounded these bluffs for millennia. The property includes multiple structures, outbuildings, and views that stretch to the horizon. According to actor Christian Slater, who once swam out to a boat anchored nearby, Simon “loved Montauk, how special it was to his soul.”

In 2017, however, erosion threatened one of the cottages on his property. Gradually, the bluff had worn away until the building sat just ten feet from the edge. As it turned out, nature didn’t care about Grammy Awards or catalog sales. Consequently, the cottage had to be moved eighty feet inland to save it from tumbling into the sea.

Certainly, there’s something poetic about that situation. A man who spent his life controlling every note, every syllable, every aspect of his career, watching the earth literally slip away beneath his feet. You can fight a lot of things. But you can’t fight the ocean.

The Lighthouse Concert

Back in 1990, Simon and Billy Joel headlined a benefit concert at Deep Hollow Ranch to save the Montauk Lighthouse. At that time, the 222-year-old structure was crumbling from neglect. Remarkably, the concert raised $270,000 and became a local legend.

Twenty-eight years later, with his farewell tour winding down, Simon made a surprise appearance at another lighthouse fundraiser. There, he performed four songs with a local band called the Montauk Project as a nearly full moon rose over the Atlantic. At seventy-six years old, he was playing songs he’d written as a teenager, standing on land where he’d raised his children with his wife Edie Brickell.

“It was a pretty epic night,” the band’s drummer said afterward. “After all, a local band getting to back Paul Simon at the lighthouse. It doesn’t get any better than that.”

The Tell: What the Estate Reveals

Consider what Paul Simon built in Montauk. Thirty acres. Oceanfront. Multiple buildings. Above all, space to breathe, to create, to exist without anyone towering over him.

In contrast, he grew up in a cramped Queens apartment where his father came home at two in the morning, so tired he couldn’t tell which driveway was his. Back then, the family had to be quiet in the mornings. There was never enough room, never enough air.

Now, however, he owns the edge of the world. The land stretches in every direction. Indeed, the only thing bigger than the property is the ocean in front of it.

When Simon sold his song catalog to Sony Music Publishing in 2021, the deal was worth $250 million. Approximately 400 songs, including everything from “The Boxer” to “Graceland” to “Bridge Over Troubled Water.” In other words, the small kid from Queens who wasn’t tall enough for the Yankees had built an empire worth a quarter-billion dollars.

Notably, he didn’t need to sell it. After all, his net worth was already estimated at $200 million. He could have held onto the rights forever, kept control like he always had. Instead, he let it go. Perhaps, at eighty, you stop needing to control everything. Or perhaps you finally trust that the work speaks for itself.

The Father He Became

These days, Simon coaches his son’s baseball team. He married Edie Brickell in 1992 and together they raised three children, splitting time between properties in New York, Connecticut, Texas, and Montauk. Unlike his own father, he plays with his kids regularly. As a result, he’s present in ways Louis Simon, with his late-night gigs and exhausted mornings, couldn’t be.

In 2002, he wrote “Father and Daughter” for his daughter Lulu, a song so tender it earned an Oscar nomination. Meanwhile, his son Adrian sang backing vocals. Ultimately, the man who grew up feeling invisible, who transformed that pain into six decades of music, had become the kind of father who writes songs for his children.

Paul Simon Hamptons Legacy: Still the Kid at the Edge

Recently, someone spotted Simon at the Montauk farmers market, just standing there, holding corn. The richest folk-rock songwriter alive, buying produce like any other dad on a Saturday morning. Worth $200 million after the catalog sale. And still five foot three.

In 2018, he retired from touring, playing his final concert in Queens, where it all started. Yet Montauk remains. The estate on the bluffs. The lighthouse he helped save. The ocean that keeps eroding the land no matter how much money you have or how many Grammys sit on your shelf.

Perhaps that’s why he chose it. He passed on Southampton with its social climbing, skipped East Hampton with its celebrities and photographers. Rather, he chose Montauk. The end of the island. The place where there’s nothing left to prove because there’s nowhere left to go.

Think about the kid who watched Art Garfunkel get all the attention at the fourth grade talent show. Consider the teenager too short for the Yankees. Picture the songwriter whose mother said his partner had the better voice. Somehow, he took all of it, every slight and every wound, and turned it into “The Sound of Silence” and “Graceland” and “Bridge Over Troubled Water.”

And then he bought himself an ocean.

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Related Reading: Read more celebrity Hamptons origin stories at Social Life Magazine, including coverage of Billy Joel, Howard Stern, Jerry Seinfeld, Steven Spielberg and the Long Island icons who shaped East End culture.