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The Overdue Oscar Winner

It’s been twenty years since Leonardo DiCaprio’s first Oscar nomination. Will this be the year the Wolf of Wall Street actor finally brings home the gold?

On a snowy night in New York last week, Leonardo DiCaprio looked out at the crowd of hundreds who had braved the weather to hear him speak at the Ziegfeld Theater about his collaborations with director Martin Scorsese—the latest of which, The Wolf of Wall Street, would be screening later that night. The event’s moderator had plenty of questions for DiCaprio, and the actor answered them all with the kind of cerebral sincerity that has become his hallmark. But, really, with the Oscars right around the corner, there was only one question on everyone’s minds: Will this be the year he finally wins an Academy Award?

DiCaprio, who received his fourth and fifth Oscar nominations for starring in and producing The Wolf Of Wall Street, is now 39 years old—which means it’s been twenty years since his first nomination (for his unforgettable performance in 1993’s What’s Eating Gilbert Grape). If Academy voters choose DiCaprio’s performance over those of other buzzed-about Best Actor contenders like Dallas Buyers Club’s Matthew McConaughey or 12 Years A Slave’s Chiwetel Ejiofor (who won the BAFTA), he’ll have Scorsese, in large part, to thank for it.

“I have been doing this since I was 13,” said DiCaprio. “At the center of it is this amazing sort of accidental collaboration that I have gotten to have with Marty.”

Cameron Diaz, Martin Scorsese and Leonardo DiCaprio in Cannes for Gangs of New York in 2002

In the years following 1997’s Titanic, then the highest-grossing film of all time, DiCaprio was, as his character Jack would say, the king of the world—and could have starred in any kind of movie he liked. But rather than toplining a blockbuster franchise or cranking out a string of rom-coms, DiCaprio had a singular vision: to work with Scorsese. “I tracked down the only screenplay that I knew that had a character for me in it, and that was Gangs of New York,” DiCaprio told the Ziegfeld crowd. “I came to [Scorsese] and I proposed myself to develop it with him and make the movie with him.”

2002’s gritty Gangs of New York allowed DiCaprio to further distance himself from his post-Titanic heartthrob image—something he’s never quite been comfortable with—and the two re-teamed for 2004’s Howard Hughes biopic The Aviator; then for 2006’s The Departed—which nabbed Scorsese his first Academy Award for directing; and for 2010’s noir thriller Shutter Island.

Their latest—and most outlandish—collaboration is The Wolf of Wall Street, a sex, drugs and booze-saturated look at the gluttonous career and travails of broker Jordan Belfort. DiCaprio has spoken often of the comfort level he feels with Scorsese after years of working together—the kind of trust that allows an actor to safely feel he can go anywhere a role requires. “Marty really infused all the actors with the idea that we were in a sort of modern day Roman Empire,” DiCaprio said. “We were hedonistic to the utter extremes. It was almost like a giant Hieronymous Bosch painting. I mean, anyone was doing anything at any given time.”And so it is we see scenes in which DiCaprio as Belfort dry-humps a flight attendant, hurls lobsters at FBI agents, holds a lit candle in his rectum and snorts cocaine off a prostitute’s derriere (for starters).

DiCaprio and Scorsese on set of The Wolf of Wall Street

DiCaprio has dazzled in his other Oscar-nominated roles over the last two decades. But there’s something about his performance in Wolf—a kind of raw, feverish ferocity that we have never seen from him before—that just may sway Academy voters in his favor this time. “I’m the first one to say I think a lot of [Belfort’s] actions were deplorable,” DiCaprio told CBS News, but “he came in there with the attitude of wanting to have the American dream. And so [many] of Marty’s movies—and this movie is another one like that—are about the pursuit of the American dream, the corruption of that dream, and the sort of hustle that it takes to get there.”

Of course, DiCaprio himself is something of a walking embodiment of the American dream. As a kid who lived in a seedy neighborhood near Hollywood Boulevard in the 1970s, DiCaprio “got to see how the other half lived,” he told Variety, when he won a scholarship to a school in ritzy Westwood. “If I could only get my shot,” he said, “I would never waste the opportunity.” Now, of course, the man’s considered one of the great talents of his generation and is one of the highest paid actors in show business. He’s donated millions of dollars to charity and is heavily involved in environmental causes.

To some, winning that golden statuette on March 2 might seem like the ultimate cap to his success. But DiCaprio—who has said he’s never much cared about awards—is already winning in the ways that matter most to him—like making the kinds of movies he believes in. Wolf is “a reflection back to the era of the ‘70s, the films that I was so moved by,” he said at The Ziegfeld, “because the director was able to put their vision up on screen without too much interference.” The version of The Wolf Of Wall Street we see in theaters “is the director’s cut,” he said, “and that’s something that you’re not going to see very often nowadays. That’s what I am absolutely most proud of about making this movie.”

If he does happen to bring home the gold on Oscar night, don’t expect DiCaprio to rest on his laurels. Even now, upon his fifth Academy Award nomination, “I always feel like a kid in this industry,” he said. “I always feel like, OK—I’ve got my foot in the door. And now, I’ve got to run with this opportunity.”



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