Oscars 2014: When Will Leonardo DiCaprio Finally Win?

After two decades of stellar performances, Leonardo DiCaprio still doesn't have an Academy Award. What gives?

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CARL COURT / AFP/Getty Images

Leonardo DiCaprio poses after presenting an award at the BAFTA British Academy Film Awards at the Royal Opera House in London on February 16, 2014.

After a stellar award season, the 86th Academy Awards are this weekend and — by almost anyone’s measure — Matthew McConaughey has a lock on the Best Actor Award.

Though this year has seen fierce competition from his co-nominees Chiwetel Ejiofor, Christian Bale, Bruce Dern and Leonardo DiCaprio (more on him in a minute), there’s been an undeniable groundswell of support for McConaughey. His role in Dallas Buyers Club certainly checks all the boxes typical of an award-winning performance: he lost a dramatic amount of weight for the role; he plays a real-life character who not only suffers from a deadly illness, but also heroically fights a weighty cause for others; and he’s already proven at other award ceremonies that he can hit a humble, charming and funny acceptance speech out of the park. Few would be surprised to see him snag the statue come Sunday night.

However, it’s often the case that Academy doesn’t necessarily reward individual performances, but frequently gives awards to those who probably should have won at some point in the past — but were overlooked — or those who have a body of consistently stellar work. That explains why the McConnaissance — the transformation of McConaughey from the shirtless rom-com star into a powerhouse actor who tackles challenging and varied roles — has been such a big part of the pre-Oscar conversation. McConaughey deserves the award, some say, not only because of Dallas Buyers Club, but also because of his great recent roles in Mud, The Paperboy, HBO’s True Detective and, funnily enough, The Wolf of Wall Street.

But the buzz over McConaughey’s career transformation and award chances raises a question: When will it be Leo’s turn?

When you look over his career, it’s astonishing to think that DiCaprio — who has been acting in critically-acclaimed films for 20 years now — has yet to win an Oscar. In fact, his nomination for The Wolf of Wall Street marks only the fourth time he’s received a nod over the course of many diverse performances. When McConaughey fans discuss how the actor has made a calculated choice to take on deep and challenging roles in recent years, they tend to ignore the fact that DiCaprio has always taken on such roles.

Over the years, DiCaprio has moved from genre to genre, skillfully tackling romance (Titanic), crime capers (Catch Me If You Can), and blockbusters (Inception). He’s even done Shakespeare! From playing an abused stepson (This Boy’s Life) to a young pyromaniac (Marvin’s Room) to a tortured undercover cop (The Departed) to a disenchanted suburbanite in a broken marriage (Revolutionary Road), DiCaprio has made an entire career out inhabiting gripping roles.

And while the Academy has given DiCaprio a nod here or there over the years — for What’s Eating Gilbert Grape, The Aviator and Blood Diamond — he’s never actually had the chance to deliver an acceptance speech. Though his turn as stockbroker-turned-crook Jordan Belfort in The Wolf of Wall Street is impressive — the scenes where he is high on Quaaludes particularly so — the general consensus says he won’t be taking home the trophy this year, either.

Of course, similar arguments could be made for Christian Bale and Bruce Dern, who have also had long and varied careers, but, then again, Bale already has one Academy Award under his belt and Dern has only rarely played the lead. (Chiwetel Ejiofor, who could well take the prize on Sunday, is the breakout here, but will surely have plenty of nominations in the future — no matter what happens.) And while award ceremonies are rarely truly fair, it will certainly sting just a little more sharply for Leo — who, along with Paramount, has mounted a full-force award campaign for Wolf over the last few weeks — if he’s to once again get the shaft.

No matter what, there’s little doubt that DiCaprio will have the opportunity to thank the Academy in the future. The question is: if not now, when?