Leo Could Have Won An Academy Award For This

by Aly Semigran

December 25, 2014 marks 10 years since the release of The Aviator, director Martin Scorsese's epic Howard Hughes biopic starring his muse and perennial Oscar snub, Leonardo DiCaprio. The actor disappeared completely into Hughes, a role that required a mental and physical transformation. The performance earned DiCaprio his second Academy Award nomination, though it was his first for Best Performance By An Actor in a Leading Role. But, in the pantheon of DiCaprio Oscar snubs, where does The Aviator rank?

The Aviator certainly seemed like it had all the ingredients for an Oscar victory for Leo. He played a real-life person who faced challenges; he won a Golden Globe before the Oscars; he was directed by the prestigious Martin Scorsese; and he starred in the most nominated film of that year (11 in total). Ultimately, DiCaprio lost to Ray's leading man Jamie Foxx and while Scorsese's The Aviator won the most Oscars at the 77th Academy Awards, it was bested by Clint Eastwood's Million Dollar Baby for Best Picture.

On paper, it looked like The Aviator would be DiCaprio's bona fide Oscar movie, but even his impressive turn as the eccentric American billionaire wasn't his most surprising snub. In honor of The Aviator, we've ranked all of DiCaprio's best shots at the golden statuette, both for his Oscar-nominated, and his unforgivably non-nominated roles.

Oscar nominations odds:

4. Blood Diamond

With all due respect to Leo, it's nothing short of a miracle he was even nominated for Best Actor in 2007 for his performance in Blood Diamond. Between that terrible South African accent and the fact that he was against shoo-in Forest Whitaker (The Last King of Scotland), this was a no-hope year for the star who had a far-better performance that same year in The Departed.

3. The Wolf of Wall Street

If there was an Academy Award for GIFs, DiCaprio's rubbery moves as Jordan Belfort would have been the undisputed champ. Unfortunately for the star, he was up against Dallas Buyers Club's Matthew McConaughey in the midst of the McConaissance. While DiCaprio's performance—which earned him a Golden Globe— was impressive as it was over-the-top (the Academy has no issue with scenery chewing), the very R-rated black comedy rubbed too many voters the wrong way.

2. The Aviator

See: above.

1. What's Eating Gilbert Grape?

DiCaprio's heartbreaking turn as the developmentally disabled Arnie in this 1993 dramedy not only remains one of the actor's most effective performances, but arguably his very best. Left in the hands of a lesser actor, Arnie in What's Eating Gilbert Grape? could have been an offensive stereotype, but DiCaprio didn't allow that to happen. A pretty impressive feat for someone who was relatively new to Hollywood and just 19-years-old at the time. In any other year, the Academy would have likely rewarded the young star, but DiCaprio was nominated in what turned out to be one of the most controversial wins in the Best Supporting Actor category. DiCaprio was bound to lose at the 66th Academy Awards to Schindler's List star Ralph Fiennes. Instead, they both shockingly lost to The Fugitive's Tommy Lee Jones. Both Fiennes and DiCaprio are still, unforgivably, Oscar-free to date.

Non-Oscar-nominated odds:

4. Titanic

Titanic wasn't just a movie in 1997, it was a pop culture phenomenon. It tied Ben-Hur for the most Academy Award nominations ever (14 in total), yet somehow one of them wasn't for DiCaprio as the dreamboat Jack. That said, even if the actor had been nominated, he likely wouldn't have won, considering none of Titanic's eleven Oscars were for the film's performances. Plus, DiCaprio had the unfortunate mark of being a teen idol at the time, which rarely bodes well for being taken seriously.

3. Catch Me If You Can

DiCaprio's charming turn in Steven Spielberg's critical and box office hit Catch Me If You Can not only showed the star's range, but during a year when the Oscars were nominating pretty fast and loose (Johnny Depp got one for the first Pirates of the Caribbean movie), he had as good a chance as any.

2. The Departed

The Departed had some wicked great performances, including one from DiCaprio as an anxious undercover cop. Somehow, DiCaprio didn't get a Best Actor nomination in a year when the Academy finally decided to right some long-running wrongs. (See: Scorsese finally winning for Best Director.) Instead, he was inexplicably nominated for Blood Diamond.

1. Django Unchained

Boy, did the Academy drop the ball on this one. DiCaprio played one of the most deplorable baddies on screen in recent memory and did so brilliantly and unflinchingly. The snub seems especially crazy when consider the Academy loves rewarding memorable supporting roles for villains. (See: Heath Ledger in The Dark Knight and Christoph Waltz in Inglorious Basterds.) Had he been nominated for Best Supporting Actor in 2012, he surely would have won.