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The Wolf of Wall Street Can’t Sleep

You can see why Leonardo DiCaprio wanted to play Jordan Belfort in the movie.

The courts at the tennis club in Manhattan Beach are full, and the pool is overflowing with bikinis. It’s a brilliant summer afternoon, and over at the juice bar, drenched in sweat after hitting for an hour or so, Jordan Belfort and I are parked on stools and talking about his Big Problem. It’s plagued him since he was a child. Even in prison, he couldn’t make it stop.

“I can’t sleep,” he tells me as the waitress arrives to take our order.

“Oh my God!” she says with a gasp. “You look just like Jordan Belfort!”

Belfort looks confused. He doesn’t know what to do. He’s never been recognized like this before.

“Actually,” the waitress goes on, “we just looked you up on the Internet. You are Jordan Belfort!”

Then the gushing starts. She tells him what big fans she and her friends are of his books, that she follows his motivational-speaking career on the web. Juice Bar Woman is a bona fide Jordan Belfort groupie.

“Can I get a picture?” she asks, and soon her smartphone camera is clicking.

The spotting is incredible for many reasons. The city of Los Angeles and its satellite communities like Manhattan Beach make up the celebrity mecca of the universe, and among all the hot stars and not-so-hot ones who can be spotted around here, the name does not quite register. Jordan Belfort? And Jordan Belfort is also a convict, one of a particularly loathed class—a white-collar crook who duped innocent investors to finance an insatiable greed. Belfort was convicted of scamming more than $100 million throughout the nineties to finance a hedonistic paradise. Stratton Oakmont, the firm he started, became a kind of cult. “It should have been Sodom and Gomorrah,” Belfort would later write. “After all, it wasn’t every firm that sported hookers in the basement, drug dealers in the parking lot, exotic animals in the boardroom, and midget-tossing competitions on Fridays.”

Belfort’s background in finance was limited. After dropping out of dental school, he sold frozen lobsters and steaks door-to-door; one of his first experiences in sales came from hawking ices as a kid. He proved to be a great talker and fearless mimic, modeling himself after his hero, Gordon Gekko, the ruthless corporate raider in Wall Street, a favorite film, and assumed what he called “a devilish alter ego.”

It was a truly epic scam, in which he used his powers of persuasion to screw investors and then train a small army to do the screwing for him. But eventually, Belfort sank his own empire. He spent some of his fortune on megamansions, only to have the government seize them. He purchased his own helicopter, only to almost crash it on his front lawn while flying it stoned. He owned a 166-foot yacht built for Coco Chanel, only to tell the captain to steer it into a storm and nearly kill himself, his friends, and his crew before the ship sank in the Mediterranean. Even with the hundreds of prostitutes he claimed to have hired, Belfort struggled to perform. He was taking so many drugs that his penis, as he writes, had taken the form of a “No. 2 pencil eraser.”

It was in prison that Belfort discovered his talents were transferable. His cube mate, or “cubie” (at his facility, there were no cells), was Tommy Chong of Cheech and Chong fame. Chong laughed so hard at Belfort’s stories he pushed Belfort to write them down and get them published. Employing the same zeal that made him a financial-industry tycoon, Belfort set out to become a writer. In prison, he studied Tom Wolfe’s Bonfire of the Vanities, taking notes on character development, dialogue, tone. He then applied the Wolfean techniques to his own tales, writing two memoirs that detail his quest for fortune and approval.

And, now as then, people cannot get enough of Jordan Belfort. He’s using the same skills, working the same stories, only this time, the gig is entirely legal. His ruthless rise and self-destructive fall was ripe for a big Hollywood production. Leonardo DiCaprio signed on to play Belfort, with Martin Scorsese directing. After many snags in production, The Wolf of Wall Street will finally be released next month and in time for Oscar season.

Back at the tennis-club juice bar, Belfort still can’t believe it: Leonardo DiCaprio playing him? During production, Belfort even coached DiCaprio personally on the stages of a ’lude high (“tingle,” “slur,” “drool,” “amnesia,” and on), with Belfort rolling around in DiCaprio’s living room. He laughs about it now, but before he went to prison, Belfort had become a kind of neurotic, Long Island version of Scarface. “I was in the midst of a cocaine-induced paranoia that was so deep I’d actually taken a few potshots at the milkman with a twelve-gauge shotgun,” he writes in his first book. After that, he nearly killed himself. “It looked beautiful, a purple pyramid,” he writes of morphine pills piled up in his hand. “I threw them back and started chewing.” The drugs. The greed. That always empty feeling. The Big Problem.