The reason Leonardo DiCaprio hasn’t won an Oscar

Every Academy Awards ceremony draws criticism in one form or another, and this year the majority of social media boo-birds looked away from Ellen Degeneres, away from John Travolta (how can you get mad?) and settled upon the branches of the Best Actor race. “Leonardo DiCaprio was robbed again,” they said.

The four-time nominee gave an electrifying performance in “The Wolf of Wall Street.” He was Jordan Belfort inside and out, the clear epicenter of another brilliant Martin Scorsese film, a role full of carnal strength and uncontrollable weakness of character. It was the best performance of his career.

But it was not the best performance of the year by an actor in a leading role. At least the Academy of Motion Picture Arts and Science didn’t think so, and frankly, neither did I.

If I had a vote, it would’ve been for Chiwetel Ejiofor, who, with the camera constantly fixed on his face, communicated the powerful anguish, longing, despair and hope of the slave experience. Or, I would’ve chosen the Oscar winner, Matthew McConaughey, whose “McConaissance” I’ve watched grow the last few years, with “Dallas Buyers Club” the pinnacle of his transformation. Was he better than DiCaprio? That’s a close call. But McConaughey’s achievement is the bigger of the two.

That sentiment, right there, tells you all you need to know about why McConaughey won an Oscar on March 2, and DiCaprio didn’t.

But more on that in a minute. Of course, we can’t fairly assess quite why DiCaprio hasn’t won an Oscar until we look at his past nominations and losses.

• 1994, Best Actor in a Supporting Role for “What’s Eating Gilbert Grape”
• 2005, Best Actor in a Leading Role for “The Aviator”
• 2007, Best Actor in a Leading Role for “Blood Diamond”
• 2014, Best Actor in a Leading Role for “The Wolf of Wall Street”

In 1994, DiCaprio lost to Tommy Lee Jones (“The Fugitive”). He was 20, and only one other 20-year-old (Timothy Hutton in “Ordinary People”) had won Best Supporting Actor. Only three actors won the award when they were under the age of 30.

In 2005, DiCaprio’s best chance came as the leader of a huge Martin Scorsese biopic about eccentric billionaire Howard Hughes, but he was outshined by Jamie Foxx’s performance in the Ray Charles biopic. Another biopic would outdo him a couple years later, when his performance in “Blood Diamond” was overshadowed by Forest Whitaker’s Idi Amin in “The Last King of Scotland,” a performance that had been projected into winning so early in the race that no other nominee stood a chance.

DiCaprio’s lack of success in these previous Oscar bids could definitely be analyzed as situational. At first he was too young. Then Foxx came from nowhere with a dead-on Charles impression. And no one even so much as argued for DiCaprio to win for “Blood Diamond,” as it was not a Best Picture contender, and it wasn’t one of the major awards season films of the year.

But if everyone is suddenly arguing that DiCaprio is “the greatest actor of his generation,” could the reason he hasn’t won only be a matter of circumstance? “The Wolf of Wall Street” loss suggests there are other factors at play here.

McConaughey and DiCaprio are very similar actors on paper. Both are Type-A leading men who can command a blockbuster. (For example, DiCaprio led “Inception” while McConaughey will lead Christopher Nolan’s next film, “Interstellar.”) Both have signature styles and character types that ooze charisma. In 2013, both played morally twisted characters based on real-life people. What gives?

When you plot out career trajectory, that’s when you notice some key differences. DiCaprio was first Oscar-nominated at age 20; McConaughey just got his at age 44. Ten years ago, DiCaprio was filming “The Aviator;” McConaughey was filming “Sahara.” DiCaprio has been the same actor for 10 years, whereas McConaughey has completely redefined himself. For those who think it’s not about careers but about individual performances, you’re a bit naive, but even so: McConaughey transformed himself into an emaciated AIDS victim; DiCaprio … played another greedy contemptible rich guy.

In that light, there’s no debate. Although DiCaprio is a veteran worthy of having “Oscar winner” in front of his name, he can’t seem to get over the hump, and it seems to be a combination of his talent and his choices.

James S. Murphy over at Vanity Fair asserts that the reason DiCaprio hasn’t won yet is because he’s too cool. “Cool guys don’t win Oscars” he writes, pointing to Brad Pitt’s three acting nominations with zero wins and how actors such as Humphrey Bogart and Paul Newman didn’t win until their veteran years, after age had taken some of their “cool” away.

Murphy goes on to make a great point that Oscars are usually awarded for performances that “invite audiences to imagine themselves … as someone different,” i.e. another race/ethnicity, disabled, ill, gay, etc., but plenty of cool actors have won Oscars for acting. George Clooney has an acting Oscar for a role that wasn’t completely out of character, and I don’t think anyone would call Daniel Day-Lewis “not cool” to his face. “Cool” actors often give great performances as characters that aren’t that different from us, but “coolness” is too arbitrary a reason for DiCaprio’s dearth of Oscar wins.

Perhaps because of his coolness, DiCaprio often finds himself to be “the least interesting performer in his own movies,” which Matthew Monagle points out on Film School Rejects. His costars have received 11 nominations since his “Gilbert Grape” nod, with two of them winning Oscars (Cate Blanchett in “The Aviator” and Christoph Waltz in “Django Unchained”). Only in “Wolf of Wall Street” did DiCaprio finally manage to keep his costars, like Jonah Hill and (well, who do we have here?) Matthew McConaughey, from upstaging him with quirkier, scene-stealing supporting performances. Still, it wasn’t enough to win.

Monagle thinks DiCaprio will eventually find his way to the Oscar stage with a supporting role that allows him to be bigger and more surprising. Most of us thought Calvin Candie in “Django Unchained” would be just that, but again, DiCaprio was playing a greedy, corrupt rich guy – not a surprise.

DiCaprio has never wildly exceeded our expectations. We’ve never been surprised by the quality of his performance. That’s a problem. If he wants to win an Oscar anytime soon, he will need to surprise us, to show us something new. Robbie Collin of The Telegraph hits it on the head:

“Since the Gilbert Grape days, and Baz Luhrmann’s Romeo + Juliet, and most crucially Titanic, we’ve watched DiCaprio grow older on screen and develop his craft to the point at which we think we know him too well – where even roles like Belfort and the grotesque plantation owner Calvin Candie in Quentin Tarantino’s Django Unchained, aren’t enough to truly surprise us, or spur his contemporaries into thinking yes, this is it, this is the one he’ll get it for.”

This is why career trajectory matters when it comes to Academy Awards. DiCaprio showed us early on what he could do, but it wasn’t good enough right away to win that Oscar, so he defaulted into “great actor” status without having anything to show for it. Voters like to be surprised and wowed, perhaps above anything else, and DiCaprio can’t do that anymore because we know where the bar is with him. After missing out on the Oscar for “The Aviator,” he needed a new strategy. You don’t come back to the race with the same old horse. But he signed on to play more powerful, rich, greedy, flawed, egotistical (inherently white) characters. Only Michael Douglas (“Wall Street”) managed to win an Oscar doing that, and it took a year in which Robin Williams was his closest competition (not to mention the stock market was a hot topic in early 1987, just ask Jordan Belfort).

If we’re being honest, DiCaprio has only shown us a handful of notes as an actor: cool, yelling, stoic, slimy and vulnerable. He does those perhaps better than anyone, but that’s all we’ve seen. Either that’s all he can do (doubtful) or that’s what he feels most comfortable with. He continues to choose amazing scripts and to work with only the best directors out there (Scorsese, Eastwood, Tarantino, Zwick, Nolan, Scott, Luhrmann, Spielberg, Cameron, Mendes), but he’s totally complacent with the roles he plays. Either he’ll need to do something radically different or challenging, or his best shot at winning will be as a producer of a Best Picture winner or the “he deserves it after all these years” Oscar, the one Paul Newman, Humphrey Bogart and Al Pacino finally squeezed out later after their prime.

What’s become abundantly clear in the “poor Leo” buzz is that the public, and presumably Academy members, are ready to etch his name on that statuette. So Leo – your move.