The Wolf of Wall Street: Why do we love the Wall Streeters we're meant to loathe?

Hollywood has yet to give us a Wall Streeter worth loving. But Jordan Belfort's greed can be seductive

(Paramount Pictures)

(Paramount Pictures)

There’s a moment near the beginning of The Wolf of Wall Street—Martin Scorsese’s three-hour based-on-a-true-story romp through the excesses of a shady penny-stock boiler room in the ’90s—when the swirling cameras and testosterone-fuelled hijinks pause for a split second and the grotesquery suddenly comes into focus.

During what Leonard DiCaprio’s Jordan Belfort calls his brokerage firm’s “weekly act of debauchery,” a young sales assistant agrees to have her head shorn for $10,000. As an underwear-clad brass band and two dozen strippers march through the office, the camera lingers on the woman a beat or two longer than is comfortable—a few loose wisps of hair emerging from her patchy scalp, a fake smile plastered across her face as she tries to prove she’s a good sport. The monstrousness of the situation registers. “FYI, Danielle tells me she’s using the money for breast implants!” DiCaprio howls. “Is this a great company or what?!” The band plays “The Stars and Stripes Forever.”

Yes, The Wolf of Wall Street is satire. And yes, the finance bros at the centre of it are monsters. They ingest more drugs than seems humanly possible, sell worthless stocks to anyone they can get on the phone, paw at every woman that comes near with a kind of slobbering, animalistic desperation, and (spoiler alert) more or less get away with it.

There’s already been plenty of debate whether The Wolf of Wall Street glamorizes Belfort and his band of white-collar criminals. The film’s moral stance seems clear enough: these are cruel and ugly people, and Scorsese gives the audience enough cues to understand this.

What’s interesting is that this is even a controversy. In recent years audiences have been invited to love ruthless gangsters, drug dealers and even serial killers. We spent much of the 2013 breathlessly following the TV exploits of a murderous meth dealer. And yet glamorizing a swindling Wall Street broker seems a step too far.

The world of finance rarely fares well in Hollywood. Scorsese’s film is the latest in a line of movies that have portrayed the men of Wall Street (and they’re generally men) as avaricious devils. In Trading Places, two bored millionaires manipulate the market and toy with the lives of Eddie Murphy and Dan Aykroyd for sport. Boiler Room, also loosely based on Belfort’s exploits, follows a kid from Queens who decides to follow the “white-boy way of slinging crack-rock” and become a stockbroker. The stereotype of the soulless, materialistic investment banker was taken to its satiric end point in American Psycho. In each movie, brokers are greedy man-children who create nothing. They move piles of money around, their vast personal riches gained either through graft or dumb luck. When it comes to the big screen, Wall Streeters fall in a category with pharmaceutical manufacturers and oil company executives—untouchably unsympathetic.

The ultimate stockbroker film, of course, was 1987’s Wall Street, Oliver Stone’s scathing indictment of capitalism. Michael Douglas’s Gordon Gekko was the embodiment of American greed, a reptilian corporate raider who ruthlessly destroyed companies and jobs with the aim of fattening his pocketbook. “Greed is good” was the mantra that was intended to epitomize a decade of immoral, easy money.

Here’s the strange part: Michael Douglas has said that people approach him to say he’s the reason they got into Wall Street. It’s a reaction that surprised everyone involved in the film. “We wanted to capture the hyper-materialism of the culture,” screenwriter Stanley Weiser has said. “That was always the intent of the movie. Not to make Gordon Gekko a hero.” In fact, the real-life “wolf of Wall Street,” Jordan Belfort, began his career selling meat, and cites the rapacious Gekko as inspiration for his move to finance.

And if Gekko got one speech to set out his “greed is good” philosophy, Scorsese and screenwriter Terrence Winter give Belfort countless opportunities to sing the praises of materialism to his team of coked-up stock pushers.

“There is no nobility in poverty,” he declares. “I’ve been rich and I’ve been poor, and I choose rich every time. At least as a rich man, when I have to face my problems, I show up in the back of a limo wearing a $2,000 suit and a $40,000 gold watch.”

It’s that kind of blunt, shamelessly greedy statement that can seem like some sort of unvarnished truth—masculine worth reduced to a mere dollar figure. Next to a predator in a bespoke suit, any namby-pamby concerns about morality can seem hopelessly lily-livered and naive.

In adapting Belfort’s memoir for the big screen, Scorsese and DiCaprio didn’t set out to create a celebration of the convicted criminal. But the kind of greed Belfort describes can be seductive. Like Milton, who got so wrapped up in the delicious evil of his character Satan that he accidentally made him the hero of Paradise Lost, Scorsese takes so much pleasure in the glitz and swing and technical virtuosity of the filmmaking, that it’s easy to see the movie’s sympathies tipping in an unintended direction.

So yes, it’s very easy to see DiCaprio’s Belfort, like Gekko before him, inspiring another generation of Wall Street dudes. When Business Insider’s Steven Perlberg watched the film in New York’s financial district, Belfort’s most outrageous actions drew wild applause from the young bankers in the crowd.

Indeed, it’s our adulation of people like Belfort that might be Scorsese’s strongest critique. Midway through the film, Belfort is dismayed by a report on him in Forbes. The reporter calls him a “twisted Robin Hood who takes from the rich and gives to himself and his merry band of brokers,” pushing “dicey stocks on gullible investors.” Belfort worries that he’s sunk. The next day his office is crammed with young suits waving their resumés.

In the film’s final scene, Belfort—now a motivational speaker, having escaped with the mildest of penalties—addresses a roomful of wannabe entrepreneurs. As others have pointed out, the scene turns the camera on us, the audience. Like us, these folks know Belfort’s been to jail for his actions. And yet they look up at him with adulation. Their eyes are wide with avarice, desperate to take a little of his magic and make it their own.