August 25, 2013 9:20 pm

DiCaprio and Scorsese on The Wolf of Wall Street

By Mary Kaye Schilling

Photo: Robert Maxwell/New York Magazine

Imagine a world where a guy can make $12 million in three minutes, where blow jobs are a perk of the gig, dwarfs are tossed to raise employee morale, and inhaling anthills of coke, Scarface style, is encouraged. Now imagine a world where a studio would pass on a movie with a subject that titillating, even if it came tied in a Leonardo DiCaprio–and–Martin Scorsese bow. That’s the way things were looking back in 2008, when Warner Bros. dropped out of Scorsese and DiCaprio’s upcoming black comedy The Wolf of Wall Street. The two went on to make Shutter Island, then separated for other projects. But when a window in Scorsese’s schedule opened up in 2012, DiCaprio approached the director again. “I told Marty, ‘I don’t think we’ll be able to do a movie like this too many times in the future,’ ” says DiCaprio. “Larger-scale, R-rated dramas, like Blood Diamond or The Departed, don’t really get financed anymore.”

An independent production company, Red Granite Pictures, eventually stepped in to finance the film (Paramount is distributing), which is based on Jordan Belfort’s memoir of the same name. The book chronicles the former stockbroker’s rise and fall as the head of Stratton Oakmont, a brokerage house he founded when he was only in his late twenties. The Long Island–based boiler room bamboozled small investors out of roughly $100 million in the nineties, the heyday of cheap money, junk bonds, and spectacularly ugly ties. In 1998, Belfort was indicted for securities fraud and money laundering, serving 22 months in prison after cooperating with the FBI.

Belfort’s writing, alternately horrifying and hilarious, almost reads like a Scorsese movie. And “Marty directing was Jordan’s dream scenario, absolutely,” says DiCaprio, who plays Belfort. “When Marty couldn’t do it the first time, I set it up with a few other directors, but I never felt comfortable pulling the trigger. I was fixated on him. There wasn’t anybody else who could bring the rawness and toughness, the music, and particularly the humor required to convey the excitement of these young punks—these robber barons—taking on the Wall Street system.”

Executive producer Alexandra Milchan had brought The Wolf of Wall Street to the attention of DiCaprio’s production company, Appian Way, in 2007. Warner Bros. quickly optioned it for DiCaprio and Scorsese, more than a year before the crash of 2008. “The book personified America’s addiction to obtaining wealth at all costs, and that hasn’t changed,” says DiCaprio, who found in Belfort a micro-tale of corruption and greed. “He was a small fish in a gigantic pond, and he’d motivate his guys by telling them they were heroes for taking on the big houses. Unregulated Wall Street was like the Wild West.” The actor was captivated by the author’s singular transparency. “There was nothing Jordan wouldn’t divulge, no matter how intimate or embarrassing,” he says. “That was the attraction for Marty as well—it’s the kind of brutal honesty that got Marty into making movies like Mean Streets.”

Scorsese has dabbled in black comedy before—After Hours and The King of Comedy, of course, and long stretches of GoodFellas. But the comedic menace here isn’t violence (unless you count death-defying self-abuse); it’s Belfort’s spectacular implosion. In addition, the film offered the director his first crack at the Zeitgeist since 1983’s Comedy—Scorsese’s creepy poke at celebrity worship—as well as an entrée into a world as ripe for hyperbole as that of Vegas, the Mafia, and 1840s New York: sin, redemption, obsession, operatic displays of excess! How could he resist?

“Jordan was a brilliant guy in a world where there may be no morality whatsoever,” says Scorsese. “He got caught at what a lot of people didn’t get caught at.” As he sees it, Wolf is about what happens when free-market capitalism becomes a matter of faith. “If you look at what occurred in the world of finance—many times now and it will probably happen again—you really have to ask the questions: Is dishonesty acceptable? Aren’t people expected to go too far?”

Jonah Hill plays Donnie Azoff, Stratton Oakmont’s second in command (a composite of a few characters in the book). Azoff, if possible, is even more gonzo than Belfort, who at least regretted ripping off clients. “Jordan told me that certain people [at Stratton Oakmont] actually enjoyed hurting people,” says Hill, who, along with DiCaprio, spent time with current day traders before shooting began late last summer. “I imagine it’s a lot more politically correct and less chauvinistic now. It certainly couldn’t be more politically incorrect or chauvinistic. But it’s still very alpha male, or alpha female, depending on the person in training. People who are weak, or perceived as weak and emotional, are fed to the wolves.” At Stratton Oakmont, says Hill, the philosophy was kill-or-be-killed, and Gordon Gekko was fetishized, but so were Scarface and GoodFellas. “Those were their models,” he adds. “They kind of ran their businesses with those sensibilities.”

Belfort’s arc does sound a little like Henry Hill’s in GoodFellas—in this case, a nice Jewish kid from Bayside, Queens, with a genius for sales, gets seduced and corrupted by Wall Street. But Scorsese disputes comparisons between gangsters and stock brokers. “The parallel between the Mafia and Wall Street works only to the extent that they’re all interested in making as much money as possible, as quickly as possible.”

In Terence Winter—creator of HBO’s Boardwalk Empire (executive-produced by Scorsese)—DiCaprio found the perfect screenwriter to adapt Wolf. Winter worked in the equity-trading department of Merrill Lynch when he was in law school. “I was there on October 19, 1987, the day of the stock-market crash,” he says. “To see it happen again, on a much larger scale, in 2008, after I had written the script? That was eerie.”

His own Wall Street experience wasn’t as crazy, but the excessive testosterone and drug-fueled, locker-room atmosphere were familiar enough. And Belfort’s epic charisma was simply irresistible. “For all the bad things he’s done, he’s so utterly charming,” says Winter. “That’s why I’m glad we kept the voice-over; you need his hilarious asides.”

Which, according to Winter, is what will separate Wolf from the many Hollywood films that have already satirized the avarice of the financial world, most infamously in American Psycho and Wall Street. That and the “pretty sadistic humor,” says DiCaprio. “We take the lives of the people in the film seriously; we don’t take the genre seriously.

“Marty said to me early on, ‘No matter the genre, no matter what kind of movie, people respond to the honesty in the characters,’ ” adds DiCaprio. “We weren’t interested in sentimentalizing Jordan. We aren’t painting a portrait of someone we want people to feel sorry for. Later in the film, when his life starts breaking apart, people are going to think he’s making the wrong decisions constantly. That’s not to say that people won’t be rooting for him, because he’s a likable guy.”

DiCaprio spent weeks with Belfort. “I wanted a close relationship with him so that I could weave intimate details into the movie,” he says, “things that weren’t in the book. I was kind of the middleman between him and Marty, and I would bring pages of notes from my meetings with Jordan—things like this insane orgy on a 747 going to Vegas, chimpanzees in diapers that would skate through the Stratton offices, very intimate stuff about his relationships with women—and Marty was game to try everything. His approach was essentially to put everything onscreen and see what we responded to. It was old-school, really independent filmmaking on a larger scale.”

This is the fifth collaboration between the 38-year-old DiCaprio and Scorsese, who turns 71 two days after The Wolf of Wall Street is released (November 15). What at first seemed an unlikely alliance is obvious now: The two men are equally committed to their independence from Hollywood, even as they play within the system—or, in the case of DiCaprio, becomes one of the most popular and highly compensated actors of his generation, without ever starring in a blockbuster franchise. “Leo and I share a certain sensibility,” says Scorsese, “a temperamental affinity.” Scorsese lived through, and DiCaprio reveres, a time when films were discussed as urgently as television is now, when it was as much an art form as it was a business. Their collaborations might lack the brute-edged intensity of Scorsese and Robert De Niro’s, but that relationship was less of a partnership. Without DiCaprio, their shared sensibility—for full immersion in a comically depraved world—would never have been financed.

“Marty is brilliant at many things, but one of them is showing people doing things that are morally corrupt and still making them enjoyable to watch,” says Hill. “You root for them and adore them in some way—it’s cool and exciting to be doing something wrong.” And the same, Hill realized, applies to the guys in Wolf. “Leo and I had numerous conversations while our characters were doing really despicable things. I was disgusted by what I was doing!” Hill laughs. “There are people who won’t see the darkness of it. Spring Breakers came out while we were making the movie. I’m a big Harmony Korine fan. I saw Kids when I was way too young—probably 11—and I completely disregarded the aids plot; I just wanted to be like those guys. So now I’m 29, and I walked out of Spring Breakers thinking, Gosh, this generation is so screwed. I was really depressed by the movie. But I realized that if I was 14, I’d be like, Oh, let’s go on spring break!”

“It’s an old story, really: People can take their identification with movies and novels to some alarming places,” says Scorsese. “Some people might just zero in on the fun, exhilarating side of it. But if you’re putting a world on film, and you’re going to stay true to that world, as opposed to show it from a distance, you’re going to make it attractive and entertaining—and, by the way, the people are entertaining, and they had a great time until they got caught.”

You can’t call Scorsese a prude, not with all the violence in his films. But sex—lots and lots of sex—has never been one of his obsessions. In one scene in the film, a coked-up Belfort furiously dry-humps a first-class stewardess on a flight to Switzerland. It’s reminiscent of the alarming comedy in Scorsese’s earlier films—classic Joe Pesci stuff. DiCaprio’s natural grace remains (it was there even when he played a sadist in Django Unchained), but he’s never been so feral. And this is one of Wolf’s tamer scenes. “It’s a modern-day Caligula,” says DiCaprio, “the height of debauchery.”

The courtly Scorsese officiating over an orgy is an incongruous image—perhaps for him as well. “Before one pretty explicit sex scene,” says Margot Robbie, the Australian actress who plays Belfort’s second wife, “Marty was talking to me about my comfort level. He said, ‘Okay, so when you’re making love …’ And I was thinking, Making love? I wouldn’t really call it that. It was quite sweet and funny.” In a memorable moment of self-pleasuring early in the film, Robbie teases DiCaprio in their daughter’s nursery—a scene that took seventeen hours to shoot. “That’s a long time to pretend you’re masturbating,” says Robbie. “It was exhausting! But most of the time it was impossible to stop laughing. How could you not, when every shot was something completely absurd, and you’re directed to take everything as far as you want? I mean, there’s a naked marching band in one scene. We sank a yacht!”

I ask Hill to identify the most outrageous scene in the film. He is unable to pick just one. “I can safely say that this is the craziest performance I’ll ever give as far as what the character gets involved with.” And this is a guy who played a guy who got sodomized by the Devil in This Is the End.

Winter is momentarily stumped as well. He mentally sifts through a long list of possibilities. “Oh, yeah,” he says finally. “There’s a scene where Donnie and Jordan take a lot of vintage quaaludes from the eighties. It takes a while for them to kick in, so they keep taking more.” The result is a five-minute fever dream of apparently world-class fucked-up-ness that, among other things, introduces the potential for a new comedy team. “DiCaprio and Hill on drugs rival Laurel and Hardy,” says Winter. “When my wife read the scene, she was nursing our newborn son, and she nearly dropped the baby she was laughing so hard. You alternate between enjoyment and thinking, When is it going to stop? How can they possibly survive this? ”

Given his time on Wall Street, I ask Winter if he learned anything new writing the screenplay. “I was under the impression that we were playing on a semi-level playing field some of the time,” he says. “But when you start to uncover the layers of how things could get corrupted, you realize that the whole system can be rigged—even the government end of it. Knowing what I know,” he adds, “I don’t put my money in the stock market. I’d rather invest in pretty much anything else—like a vintage-Matchbox-car collection.”

Hill’s takeaway was more basic. “Maybe don’t do bags of quaaludes and cocaine every day for four years,” he says, and laughs. “Everything is going to feel like a letdown after that kind of sensory overload, you know? It’s like the end of GoodFellas. Ray Liotta is in witness protection. He orders spaghetti and gets egg noodles and ketchup. The rest of his life he’s going to be eating egg noodles and ketchup. He’s going to live life like a schnook.”

The Wolf of Wall Street, directed by Martin Scorsese. Paramount. Not yet rated. November 15.

Click through the gallery ahead for exclusive behind-the-scenes photos by Brigitte Lacombe.