Could 'The Wolf of Wall Street' mark the end of Leonardo DiCaprio's Oscar drought?

BEVERLY HILLS, Calif. — Leonardo DiCaprio is poking his head out of a poolside room at the Beverly Hilton Hotel.

It's afternoon, and a swarm of media outlets is lined up outside, chatting with Oscar contenders after the Academy Awards' annual luncheon for nominees. Nominated for lead actor for his role as an excess-obsessed stockbroker in "The Wolf of Wall Street," DiCaprio stands to gain plenty of attention if he's viewed, but he goes unseen.

Still, he can't conceal his curiosity. "What's going on out there?" he asks with childlike intrigue, lowering his brow. "Why are there only two people on pool floats?" Turns out, they're models hired to liven up the background of an entertainment show's feed.

"That's corny," DiCaprio says with a laugh. But surely the 39-year-old actor understands the allure of overdoing it.

Decadence is what fueled "Wolf," a film that's gained him two Oscar nominations for acting and producing. DiCaprio has been nominated for three other Academy Awards, starting with a supporting actor bid for playing a teen with autism in the 1993 drama, "What's Eating Gilbert Grape." He's been overlooked each time.

This could be his year. Is he frustrated he hasn't won?

"Here, I'll show you the card they gave me today" (at the luncheon), he says, rummaging through his pockets after setting aside the electronic cigarette he says he puffs to "relieve the stress of life." He retrieves a small white card he calls "that little football chalk-up" listing his film stats. Leaning in, he points to the portion that reads: five nominations, zero wins. With a heavy chuckle he looks up and says, "Zip!"

Nominated for lead actor Oscars for "The Aviator" and "Blood Diamond," DiCaprio has lost to Jamie Foxx and Forest Whitaker (he lost the best supporting actor statuette to Tommy Lee Jones). This year, he's up against Christian Bale, Chiwetel Ejiofor, Bruce Dern and Matthew McConaughey, who is considered DiCaprio's biggest threat for his portrayal of a rodeo-loving Texan with HIV in "Dallas Buyers Club."

"We haven't seen Leo and McConaughey paired off in any award show," says Tom O'Neil, editor of the awards prediction site goldderby.com. "The assumption is Leo can't do it."

But this wouldn't be because he lacks skill. DiCaprio, whose first big film role was opposite Robert De Niro in 1993's "This Boy's Life," has starred in a number of films that gained Oscar attention, including two best picture winners: "Titanic" and "The Departed." "Gangs of New York," "Catch Me if You Can," "Revolutionary Road," "Inception," "Django Unchained" and last year's "The Great Gatsby" have also earned Academy attention.

"It's as if the old men in the Academy look at someone like Leo and say, 'You have the money, the fame, the babes, but here's one thing you can't have,'" adds O'Neil. "We've seen a history of it. Paul Newman didn't win until he was past the age of 60. Often, if you are old or if you let yourself go to hell like Matthew McConaughey did in 'Dallas Buyers Club' by losing a lot of weight, the Academy awards you."

Many major Hollywood talents have endured Oscar snubs. Neither Alfred Hitchcock nor Stanley Kubrick ever received directing trophies. At the risk of gaining comparisons to the late actor Peter O'Toole, who was nominated eight times without a win, DiCaprio could go home empty-handed again.

He's been particularly dedicated to the Oscar campaign for "Wolf" — DiCaprio even appeared on "Saturday Night Live" with Hill. "Wolf" marks the actor's fifth collaboration with Martin Scorsese. It's a project he takes extreme pride in, largely because he was part of its development.

"The fact that I brought it to Scorsese and put the financing together ... all of these elements add a whole other level of responsibility," he says. That includes defending the racy material in the film, which has gained a bad rep for glorifying greed.

"I've never been a part of a film that had this sincere level of controversy around it," DiCaprio says. "But I want to have films out there that cater to an audience that I think is yearning for something that is a little more outlandish."

His hunch proved spot-on. "Wolf," costing $100 million to make, has earned over $230 million worldwide. "You make these movies, you work as hard as you possibly can, you put your life on hold and you hope for the best," adds the actor.