Jonah Hill on ‘The Wolf of Wall Street,’ Prosthetic Penises, and Finance Douchebags

The 'Superbad' star on his scene-stealing turn as a despicable, lude-popping stockbroker opposite Leonardo DiCaprio in Martin Scorsese’s ‘The Wolf of Wall Street.’

Mark Veltman/The New York Times, via Redux,MARK VELTMAN

Jonah Hill may be Hollywood’s ultimate wingman. There was 2007’s Superbad, his breakout role, where he served as the round, boisterous base below a reticent Michael Cera, forming a metaphorical exclamation point; Get Him to the Greek, where he was tasked with transporting Russell Brand’s heroin-smuggling rocker across the Atlantic; his Oscar-nominated turn as Peter Brand, a young sabermetrics expert opposite Brad Pitt in Moneyball; and as a high school-infiltrating undercover cop alongside Channing Tatum in 21 Jump Street.

Now, he’s back in his most despicable—and high-profile—role to date. In Martin Scorsese’s The Wolf of Wall Street, Hill plays Donnie Azoff, a coke-snorting, lude-popping, hooker-sexing stockbroker opposite Jordan Belfort (Leonardo DiCaprio) in the early ‘90s-set black comedy. Sopranos scribe Terence Winter adapted the film from Belfort’s memoir of the same name. DiCaprio has described the film as “a modern-day Caligula”; a non-stop symphony of gross excess. It could be retitled The Gordon Gekko Chronicles, and serve as a twisted prequel to Oliver Stone’s Wall Street.

And Hill fully embodies Donnie, a morally bankrupt clown with shiny, capped teeth, suspenders, and a gravelly voice. He’s an emasculated man who’s suddenly granted the opportunity to swing his balls back-and-forth like a cocky pendulum, and his transformation is shocking.

“There have been very few times where I’ve gone, there’s no one else to play this part but me,” says Hill. “Those times were Superbad, Cyrus, and Moneyball, and now this film. Everything else I’ve done I’ve been proud of and had a great time, but they weren’t situations where I thought: I have to play this part.”

The 30-year-old actor was primarily known for his comedy chops—a product of the improv-heavy Judd Apatow talent factory. Then came his surprising turn as a demented son involved in a Spanking the Monkey-esque relationship with his mother, played by Marisa Tomei, in the aforementioned Cyrus. That role led to a dramatic opportunity in Moneyball, which opened the door to further dramatic roles.

One day, Hill got a call from his agent saying he was on a list of actors in contention to play opposite DiCaprio in a Scorsese-directed adaptation of The Wolf of Wall Street. Scorsese is his favorite filmmaker, and Hill aggressively pursued the role, reading the book and screenplay multiple times, and insisting on a meeting with DiCaprio while the two were in Mexico promoting different films. When they met, Hill told him, “I have to play this part.” “Why?” asked DiCaprio. “Because I recognize who this person is, and I think they represent a lot of what’s wrong with certain elements of society,” Hill replied. “And while I don’t like this person, I understand how to bring him to life.”

DiCaprio relayed the information to Scorsese, who met with Hill a month later. Scorsese had requested a meeting, but Hill demanded he audition for the part. “I wanted to show him what I could do with it,” he says. It was Hill’s first audition in six years.

“It was the most terrifying experience,” he recalls. “I went to Scorsese’s office and we went to this screening room and it was hot as hell, so I was so nervous and it was 100 degrees in there, and I started sweating. I had to excuse myself, go to the restroom and wash my face, and then come back and go, ‘Guys, I know this sounds really weird… but is there any other place we can do this because it’s so hot,’ and Scorsese said, ‘Oh yeah, it is too hot! Let’s go to my office.’”

Using a thick Long Island accent (his parents are from there), he acted out two scenes: one where he first meets Jordan in a diner, and the other where he berates an innocent guy on the trading floor before consuming his goldfish. “I mimed eating the goldfish,” says Hill.

For two months after the audition, Hill received regular calls from his agent saying, “Hey, you’re still in the running… they’re meeting with bigger actors, but you’ve still got a shot,” when finally, one night at dinner, he received the greatest phone call of his career. It was DiCaprio. “You’ve got it,” he said to Hill. “Scorsese just called me to ask my final thought on it, and I said let’s do it.”

In order to portray Donnie, Hill fussed over the dentures with the props department, and tweaked the thick Long Island accent he employed in his audition to a more gravelly one. And Donnie, like Belfort, is the uncontrollable id—a finance scoundrel engaged in various pump-and-dump schemes, cheating hard-working people out of their pensions and life savings by manipulating penny stocks.

“The whole movie is so unapologetic and so aggressive,” says Hill. “Donnie, while entertaining to watch, is coming from a pretty dark place. He has no impulse control, he’s a drug addict, he steals from people with no remorse. It was understood going in that there was no holding back. Every day we were doing something crazy, and it’s fun and exciting working for Scorsese, and then when I’d be driving home at the end of the day, I’d feel a wave of guilt come over me because I treated people so badly that day.”

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One of the most memorable scenes of the film involves Donnie. They’re at a party at Belfort’s garish Long Island mansion and Hill’s character is luded out of his mind. He spots Naomi (Margot Robbie), a stunning blonde who has the entire trading team’s tongues wagging. So, Donnie whips out his cock and starts beating it in front of Naomi and the entire party.

“It was a prosthetic,” says a chuckling Hill. “There were a lot of background artists on set that day who hadn’t read the script, so they just know that they’re in a scene and a guy is pulling out his genitalia and masturbating in front of them at a big party. So for them, it was really funny, but for the main characters, it’s really inappropriate and disturbing. So, I had to tell everyone that while their first instinct was to laugh, I had to take it very seriously so that we got the appropriate response.”

Some, like The New Yorker’s David Denby, have been critical of The Wolf of Wall Street’s exultant approach, fearing it may glamorize the excesses it seeks to abhor, and create a new generation of wannabe Gekkos—er, Belforts. Hill doesn’t see it that way.

“The message of the film is that excess leads you down the wrong path, and if you indulge excessively, you’ll really lose sight of things,” he says. “Everybody inside of them, even the best of us, have a speck that wants more, and wants to be rich, and wants excess, and this is a story about people who 100 percent want that.”

He adds: “Fundamentally, people who work in finance, their only goal is to be exceedingly wealthy; to be very, very rich. If your passion is just making a lot of money, it’s something I don’t understand that much, personally. You’re not doing anything that fulfills you in a way other than making money.”

Hill was never that interested in making money. At 18, while attending Bard College, he began writing and performing one-man plays at the Black and White bar in the East Village.

“I’d written a play about Hitler’s college roommate and how Hitler became evil because the roommates never included him in anything and really bullied him,” he says with a laugh. “Sometimes the plays were funny, and sometimes they weren’t. I was 18, so for me, when you’re at that age, it’s just about being offensive and pushing boundaries in order to stand out.”

He soon befriended Dustin Hoffman’s son, Jake, who introduced him to his father. Hoffman convinced a then 20-year-old Hill to audition for a part in David O. Russell’s I Heart Huckabees, which would mark his feature film debut. A bit part as a clueless eBay customer in Judd Apatow’s The 40-Year-Old Virgin followed, which led to his inclusion in the “Apatow Gang.”

In less than a decade, Hill’s gone from Huckabees to co-writing/producing/starring in the Jump Street films—a sequel, 22 Jump Street, is out next summer—and serving as the Boy Friday to stars like Pitt and DiCaprio. When I inform him of his lofty wingman status, he laughs.

“They’re all such talented, great people, and for me, it’s all about how they can make me better, and how I can hopefully make them better,” he says. “When you’re acting opposite someone like Leo, who’s the best actor of his generation, they really elevate you.”