Wolves of Wall Street
A CultureMap®
by James Waller
Published on 12/20/13

Animals occupy Wall Street. Bears claw at the stock market, sometimes ripping it to shreds. Bulls exuberantly charge, head-butting the economy forward and occasionally tossing it to dizzying heights. And then there are the wolves: traders who prey on unwary buyers or exploit regulatory weakness for their own illicit gain. They’re feared and despised, but they also fascinate, since their behavior so stunningly exemplifies capitalism’s canine-eat-canine savagery.

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Wall Street  (Oliver Stone (dir.) | film | 1987)
to  The Bonfire of the Vanities  (Tom Wolfe | novel | 1987)

The mid-1980s were boom years for Wall Street—until 1987, when U.S. and global markets tumbled in the Black Monday crash of October 19. Coincidentally, that was also the year two fictional blockbusters documented the excesses of stock market highfliers: Oliver Stone’s Wall Street and Tom Wolfe’s Bonfire of the Vanities. Both are morality tales that revel in the downfall of traders who saw themselves, in Wolfe’s phrase, as “Masters of the Universe.” Stone focuses his righteous gaze on the financial sector’s moral sickness, epitomized by the “Greed…is good” motto espoused by villain Gordon Gekko (Michael Douglas). Stone based Gekko partly on arbitrageur Ivan Boesky, who had made a pile of cash through insider trading before the Securities and Exchange Commission caught him and he was sent to jail. Wolfe’s satirical novel paints a wider canvas, taking wicked glee in the avarice and hypocrisy infecting every corner of late-20th-century New York. Rich, poor, white, black—not just financiers but also politicians, lawyers, media moguls, even clergy—all were vying for power in this jungle of a city.

Wall Street  (Oliver Stone (dir.) | film | 1987)
to  The Wolf of Wall Street  (Martin Scorsese (dir.) | film | 2013)

New York City–born filmmaker Martin Scorsese has trained his eye on several of the metropolitan area’s demimondes: from cab driving (Taxi Driver, 1976) and boxing (Raging Bull, 1980) to show business (New York, New York, 1977) and organized crime (Goodfellas, 1990; Gangs of New York, 2002). But The Wolf of Wall Street marks his first foray into the world of the stock market. Scorsese’s subject is the true-story rise and fall of Jordan Belfort (played by Leonardo DiCaprio), a stockbroker who in his 20s and 30s got filthy rich operating a “boiler room,” or “chop shop”—a brokerage that makes money by fraudulently inflating stocks’ value and selling the essentially worthless shares to chumps. This sleazy corner of the financial sector has been examined before, in Ben Younger’s 2000 film Boiler Room. Its young traders—who work for a Long Island firm resembling the one Belfort ran—fancy themselves Wall Street wolves in the mold of Gordon Gekko, the despicable yet magnetic arbitrageur of Oliver Stone’s Wall Street. They even memorize Gekko’s tirades, competitively reciting them while watching Wall Street together. Despite the bravado, they’re not wolves, just self-deluded pups doomed to be put down.

The Wolf of Wall Street  (Martin Scorsese (dir.) | film | 2013)
to  The Bonfire of the Vanities  (Tom Wolfe | novel | 1987)

It’s fun to watch the mighty crash and burn, especially when the mighty in question are parasitical stockbrokers who benefit enormously from the capitalist system while creating nothing except their own fortunes. Jordan Belfort, the charming, rapacious protagonist of Martin Scorsese’s film Wolf of Wall Street, makes hundreds of millions through sophisticated swindling, so his downfall is just deserts. (No spoiler here: You know the guy’s gonna get nabbed.) But the downward trajectory of Sherman McCoy, the Wall Street dealmaker of Tom Wolfe’s Bonfire of the Vanities, presents a more nuanced case. Sherman is an overprivileged, arrogant son of a bitch, but his descent into hell has nothing to do with professional misbehavior. And though Sherman’s knockdown is pleasurable enough to behold, his rotten luck—which begins when he and his mistress miss a turn while driving—hits him so hard you almost pity him. (In Brian De Palma’s notorious 2000 film adaptation, you do feel sorry for Sherman, who’s played too sympathetically by Tom Hanks.) Of course, real Wall Street alpha dogs are only rarely penalized for malfeasance—as demonstrated by the appalling lack of criminal indictments against those responsible for setting off a global recession in late 2007.

The Wolf of Wall Street  (Martin Scorsese (dir.) | film | 2013)
to  Leonardo DiCaprio  (b. 1974 | American actor)

Director Alfred Hitchcock was devoted to his blond muses—Grace Kelly, Kim Novak and Tippi Hedren among them. Martin Scorsese likewise has one in Leonardo DiCaprio. (Scorsese’s former muse, Robert De Niro, is—or was—a brunet, but never mind.) DiCaprio starred in Scorsese’s Gangs of New York in 2002 and has played the lead in four features Scorsese has made since: The Aviator (2004), The Departed (2006), Shutter Island (2010) and now The Wolf of Wall Street. Reportedly, Scorsese considered DiCaprio for the part of Ol’ Blue Eyes in a planned Frank Sinatra biopic. Perhaps this diverse body of work has to do with the actor’s ability to project a boyishness that can be callow, winsome and sometimes goofy, even as he thickens toward middle age. In addition to Scorsese, Steven Spielberg (Catch Me If You Can, 2002), Clint Eastwood (J. Edgar, 2011) and Baz Luhrmann (The Great Gatsby, 2013) have exploited this distinctive aspect of DiCaprio’s somewhat modest range. And perhaps it’s his particular brand of puer aeternus, or Peter Pan syndrome, that recommends DiCaprio to portray bad-boy stock whiz Jordan Belfort, despite his not physically resembling Belfort in the least.

Leonardo DiCaprio  (b. 1974 | American actor)
to  Jordan Belfort  (b. 1962 | American stockbroker)

In 2013 Leonardo DiCaprio played the most glamorous businessman-criminal in all of fiction, Jay Gatsby, in Baz Luhrmann’s frenzied adaptation of F. Scott Fitzgerald’s Great Gatsby. In his unfinished, posthumously published novel The Last Tycoon, Fitzgerald famously posited, “There are no second acts in American lives.” That claim is highly dubitable, even in the case of Gatsby, who deftly played his way through a number of acts before buying that fated mansion in West Egg. And it’s even less true of Jordan Belfort, who didn’t let a little thing like serving time for money laundering and securities fraud finish him off. After getting out of the federal pen, Belfort reinvented himself as a best-selling author, writing two accounts of his meteoric financial career and the over-the-top, booze-and-Quaalude-addled lifestyle funded by his ill-gotten wealth. (Most egregious, a drugged-out Belfort sank a 167-foot yacht that once belonged to Coco Chanel.) The formerly crooked Belfort now earns his living as a motivational speaker, promising businesses and individuals success if they follow his patented method, which he dares to call the Straight Line System. In a testimonial video, DiCaprio calls him a “true motivator.”

Jordan Belfort  (b. 1962 | American stockbroker)
to  The Wolf of Wall Street  (Martin Scorsese (dir.) | film | 2013)

In the page-turner memoirs on which Martin Scorsese’s film is based, The Wolf of Wall Street (2007) and Catching the Wolf of Wall Street (2009), Jordan Belfort happily adopts the nickname he earned manipulating stocks at Stratton Oakmont, the Long Island brokerage he cofounded. Belfort’s wolfishness isn’t in dispute. Stratton Oakmont racked up millions through “pump and dump” schemes. It created artificial demand for lousy stocks, then offloaded its own shares when a stock’s price reached its peak, leaving other investors, whom the firm itself had signed, holding worthless paper when the price inevitably crashed. But Belfort wasn’t the first so-called Wolf of Wall Street. That dubious honor belongs to a little-remembered early-20th-century con artist and market scalper who went by the name David Lamar. Nor is Belfort the most heinous kingpin-cum-defrauder in recent memory; that distinction goes to Bernard Madoff, who from the 1970s till 2008, when he suddenly confessed his crimes, operated a Ponzi scheme that ultimately robbed investors of billions of dollars. Madoff, like Belfort, may soon be portrayed by an actor whose stardom Scorsese nurtured: Robert De Niro will reportedly play him in a forthcoming HBO production, Wizard of Lies.