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"FacebookPinterestFacebookPinterestFacebookPinterestFacebookPinterest\n\nLast night, the Internet sighed another collective awwww at the sight of Leonardo DiCaprio coming short, for a typically manic turn as an unsympathetic monster in a film many people had problems with? That's not to knock Leo's work\u2014there was not just unbridled rage but real nuance in his portrayal of a total asshole, and my sides still hurt from that Quaaludes scene\u2014but if we're going to collectively gush every time an actor suffers an expected loss, we've got our work cut out for us.\n\nSure, the \"don't feel bad for him 'cuz he's rich and famous\" refrain is an old argument, and a disingenuous one, too: Humans in general are bad at sitting back and counting their blessings. All-consuming desire is what makes us such a successful species. But that's really why we feel bad for Leo, right? Because we like him\u2014he is, by most accounts, a nice guy, a hard-working actor, and a charming, handsome dude who lives a fantasy existence filled with supermodels and yachts. And so maybe it's an endearing humanization\u2014that the man who dumped Bar Rafaeli is haunted in his dreams by, basically, a small golden action figure?\n\nNobody's contending that Leo doesn't, in some sense, \"deserve\" an Oscar. He is perhaps the greatest leading man working on a regular basis today. But there's a big difference between \"deserves to\" and \"should have by now.\" Every year's Awards are their own animal, each pool of worthy (and sometimes unworthy) nominations a game of chance in the quest for immortality. And with Leo's snubs, it's not like we're really in farcical territory yet. The Wolf of Wall Street was Leo's fourth nomination in the Best Actor category\u2014his directorial benefactor, Martin Scorsese, had to wait until his sixth nomination to win Best Director (2006, for The Departed), a very full and acclaimed twenty-six years after his first (1980, for Raging Bull). The recently passed Peter O'Toole, as charming and enigmatic an actor as will ever live, was nominated for acting eight times, winning only the dreaded honorary Academy Award in 2003\u2014which he initially tried to decline, saying he wanted some more time to \"win the lovely bugger outright.\" Or consider Redford\u2014touted early as a favorite to win Best Actor this year, which would be his first acting win and only second nomination in that category; he didn't even get the nod.\n\nBut just like O'Toole lost to the likes of Brando in The Godfather and De Niro in Raging Bull, not all losses are created equal. (And on that note, we say O'Toole's first nom, for Lawrence of Arabia, should have beaten Gregory Peck in To Kill a Mockingbird, as well as anyone in anything else.) Who should DiCaprio have beaten by now? Jamie Foxx in Ray? Forest Whitaker? To ask when Leo will win an Oscar, or what he needs to do, or if he ever will, seems both premature and overly deterministic, like those who said LeBron James wouldn't win a ring until he \"really wanted it,\" or some such garbage. Sometimes you do it all and come up short. That's how life works. Leo's done and won plenty, and here's hoping he someday wins the rest.\n\nWhat does Leonardo DiCaprio have to do to win an Oscar? Exactly what he's doing. And maybe throw in a prayer or two.\n\nDennis Tang (@tangaciousD) is a assistant editor at GQ"^^<http://www.w3.org/2001/XMLSchema#string>
<http://www.gq.com/story/leonardo-dicaprio-oscar-snub>