Leonardo DiCaprio is a damn fine actor. He's also acted in some damn fine movies. According to his IMDb page, he's won 55 awards over the course of his storied career, and two of those are Golden Globes. Zero are Oscars. With DiCaprio up for yet another Globe for his role in The Revenant on Sunday, it's time to revisit the question: Why hasn't Leo won an Oscar as well?
He certainly knows how to throw himself into his work. He was practically unrecognizable in J. Edgar and The Aviator, and he seems willing to go the extra mile, no matter what. In The Revenant alone, DiCaprio actually waded through frigid Canadian rivers, slept in animal carcasses, and ate raw bison liver. Most impressively, he can actually pull off an authentic-sounding Boston accent, something that eludes near every actor who's ever attempted it. (Let's face it, he's not exactly hard to look at either.)
Maybe it has nothing to do with his acting. Maybe he offended some important academy members at a cocktail party by telling an off-color joke. Maybe a witch put a curse on him as an infant. Or maybe he's just always up against better actors? Let's take a look.
Best Supporting Actor, 1994
What's Eating Gilbert Grape? could have just as easily been called Arnie Grape is a Charming Young Man With a Hot Older Brother. How was this not a lock? The Oscar went to... Tommy Lee Jones for The Fugitive. Oh, snap. I literally just quoted one of his lines from that movie last week. A twenty-one year old movie. OK, fine, Tommy wins this round.
Best Actor, 2005
Alright, last time around, Leo was just a kid, but by 2005, he'd established himself as a serious actor. Look at the dedication! Look at his eyes! He's not messing around! Who could top that? Jamie Foxx did. For Ray. I blame this on the fact that everyone on Earth is quite familiar with Ray Charles, but there's no Pepsi commercial starring Howard Hughes. We had no frame of reference. Not fair.
Best Actor, 2007
Honestly, I don't recall ever hearing about the movie Blood Diamond. Maybe it was bad? Or maybe Forrest Whitaker was amazing as Idi Amin in The Last King of Scotland. Biopics are very often Oscar bait. Or, here's another theory: when I went on my search for Blood Diamond gifs, Leo was smoking and/or drinking in almost all of them. Maybe Hollywood doesn't want to reward that kind of lifestyle, hmm?
Best Actor, 2014
Oh, come on, Leo was fantastic in The Wolf of Wall Street! Who knew he could be so funny? Tell me one better actor than him. Matthew McWhatNow?? McConaughey was a great supporting actor in Wolf, but apparently he was even better as the star of Dallas Buyer's Club. While I agree that the real life Ron Woodruff, activist and noble drug smuggler, was a much better person than the real life Jordan Belfort, crooked stockbroker and all-around maniac, Belfort's story was so fun to watch. I don't like to cry at the movies, so sue me.
Best Picture, 2014
DiCaprio also produced The Wolf of Wall Street, and it was up for Best Picture... the same year as 12 Years a Slave. That is some real shitty timing, Leo.
And there's your answer. Leonardo DiCaprio just has incredibly bad timing, going up against the one person who could beat him, year in and year out. When you keep competing with strong actors in biopics (especially when they play sympathetic characters), you're kinda screwed.
He shouldn't feel bad though — even Tom Hanks doesn't always win when he's nominated for an Oscar (which is a crime). With a third Golden Globe win all but guaranteed this year, will DiCaprio finally nab a coveted Oscar this year as well? Well, this is the same year that Eddie Redmayne played transgender pioneer Lili Elbe in The Danish Girl, so... no. Sorry, Leo. Just bad timing again.
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