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Why can’t Leo DiCaprio seem to win an Oscar?

Actors Leonardo DiCaprio (L) and Christoph Waltz at the Oscars. (Photo by Christopher Polk/Getty Images)

Leonardo DiCaprio has been nominated five times for an Academy Award. And five times, both he and his fans have been disappointed.

DiCaprio failed yet again Sunday to lock down the Academy Award for Best Actor, passed over for Matthew McConaughey in “Dallas Buyer’s Club.” Poor Leo, said the Internet — literally. The hashtag #poorleo has been shared some 12,000 times in the past 24 hours.

DiCaprio sits at that rare intersection of popular and critical consensus: Pretty much everyone thinks he’s good. And yet every year, without fail, the prolific and no-longer-baby-faced actor finds himself clapping for someone else.

There was “What’s Eating Gilbert Grape,” in 1993. (Best supporting actor — Tommy Lee Jones won for “The Fugitive.”) Then there were best actor nominations for “The Aviator” in 2004 and “Blood Diamond” in 2006. (Those went to Jamie Foxx and Forest Whitaker, respectively.) This year, DiCaprio doubled his chances with “The Wolf of Wall Street,” since he was up for both Best Actor for his portrayal of despicable stockbroker Jordan Belfort, and Best Picture, for his work as one of the film’s dozen producers.

He hasn’t fared too well in other competitions, either: DiCaprio has won zero Screen Actors Guild Awards, of the eight he’s been nominated for; and he’s won only two Golden Globes, of 10 nominations there. He may arguably be one of the losing-est leading men in recent Hollywood history.

But … why? Wrote Telegraph film critic Robbie Collin:

DiCaprio’s continuing inability to land an Oscar, despite being one of the most feted and bankable actors in the business, is one of the inexplicable quirks of the awards-season ecosystem, a kind of strange and mystical natural phenomenon, like bioluminescent plankton, or the moving rocks of Death Valley.

Actually, as Collin himself goes on to explain, DiCaprio’s losing streak is probably a lot less mystical than all that. There are a couple of theories, the simplest of them being that Leo has just had the terrible luck of coming up against even better actors every year. (If only Whitaker wasn’t up in 2006!)

Another school of thought holds that he just hasn’t taken the right roles — the big, transformative, paradigm-shifting roles that transcend the actor’s off-screen persona and excite the Academy. Think Daniel Day-Lewis, unrecognizable in “Lincoln,” or Colin Firth in “The King’s Speech.”

And then there’s a related problem, a specter that everyone likes to evoke when his favorites fail to win: The Academy is, frankly, pretty darn biased. The organization’s 5,000-plus members, an anonymous crew of actors, cinematographers and other industry professionals, are more than 90 percent white and more than 70 percent male. They tend to favor certain types of movies — serious dramas, biopics, epic histories — with certain types of comfortable, complete plot arcs.

That doesn’t exactly describe “Wolf of Wall Street,” arguably DiCaptrio’s best, and most uneasy, performance. His character, Belfort, is so easy to hate that critics reportedly left the film during screenings. And we won’t spoil the three-hour epic for those who haven’t seen it, but it doesn’t exactly end on a redemptive note.

Leo’s career can, though — he has lots of time! And reassuringly, he’s not the only leading man in Hollywood who got passed over for decades before his big win. Paul Newman scored seven Oscar nominations, but no actual awards, between 1959 and 1983. Al Pacino waited 20 years before winning Best Actor for “The Scent of the Woman,” in 1993.

It’s just an inherent quirk in the system, Peter Lehman, the director of the Center for Film, Media and Popular Culture at Arizona State, told the Christian-Science Monitor in 2012. The awards are, in many ways, simply more about the Academy than the actors themselves.

“The Oscars give Hollywood a chance to put forward what they perceive as the most favorable image of themselves in any given year,” he said. “The Oscars are more about how the industry would like the public to perceive their films and what is best about them.”