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Is Leo’s Quest For An Oscar About To End?

​In 2014 the stage was set. Leonardo DiCaprio had won Best Actor in a Motion Picture Musical or Comedy at the Golden Globes and all he had to do was hold off the front runner for a few more lengths. The Wolf Of Wall Street was all the rage during January and Leo could smell the highest prize in acting. As February began, like a well trained horse coming off the final turn, Matthew McConaughey caught fire and it became clear that Dallas Buyers Club would clean up the acting awards on the men’s side at the 86th Academy Awards.

Now the stakes are higher than ever. While the nominees have yet to be announced, he will likely receive his fifth Oscar nomination. What’s different this time is his competition. It is an uncharacteristically weak field for actors this year and that has to be factored in. While Hollywood can be unpredictable to a fault, I’m guessing that his competition at the 88th Oscars will look something like this:

-Eddie Redmayne for The Danish Girl
-Michael Fassbender for Steve Jobs
-Matt Damon for The Martian
-Christian Bale for The Big Short

There’s a chance that Will Smith (Concussion) or Steve Carell (The Big Short) knock one of these guys out, but my guess is that this is the bulk of Leo’s competition.

It won’t be a walk in the park. We learned last year that the Academy loves Eddie Redmayne almost as much as they like girls in boys clothes or boys in girls clothes. Michael Fassbender is another guy who the Academy could be quick to embrace. With only one past nomination (ironically as a supporting actor who lost to Dallas Buyers Club), Fassbender’s portrayal of Steve Jobs will get him some serious looks.

Christian Bale presents a major obstacle for any man nominated for Best Actor. With a win in the supporting category for The Fighter and a nomination two years ago for American Hustle, Bale is slowly morphing into a living legend. Generally I shy away from picking actors who are up against other actors in the same movie, so a nomination for Carell would certainly lower Bale’s chances. Still, you never want to see him on the ballot, especially when you’re Leonardo DiCaprio.

Then we come to Matt Damon. Damon is looking to do the same thing Leo is, win an Academy Award in an acting category. Winning back in 1997, that award went to both Damon and Ben Affleck for writing Good Will Hunting. Damon has since been nominated for two Oscars, losing to Jack Nicholson in 1997 and to Christopher Waltz in 2009 as Best Supporting Actor. With a Golden Globe win already under his belt for The Martian, Damon is likely DiCaprio’s stiffest competition this year.

What makes DiCaprio different and unlike other actors who have never heard their name called by the Academy (see: 6 Actors Who Have Never Won An Oscar But Deserve To), is that he’s deserved to win. He’s played incredible roles over the years and has lost to some heavy hitters. In 2004 he lost to Jamie Foxx’s portrayal of Ray Charles and in 2006 he, along with the rest of the nominees, got bludgeoned by Forest Whitaker and The Last King of Scotland.

So here we stand. Nominations on the horizon and another Oscar worthy performance in the bank for Leo. Years down the road it won’t matter how he won. It won’t matter whether he took down heavy hitters or a beatable field. DiCaprio is striving, for the first time in his career, to break into the home stretch with the lead and hold off the competition for good.

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