ByIlia Palavandishvili, writer at Creators.co
I can't wait to show you my toys
Ilia Palavandishvili

Everyone seems to be pretty much agreed that this is Leo’s year to finally win that Oscar – and who can begrudge him the joy of finally getting his hands on one of those little gold dudes?

He was first nominated way back in 1993, and, while he’s won Golden Globes, Critics Choice Awards and various other accolades, the Oscars have consistently teased him with the possibility of trophies, only to yank them out of his grip. Poor Leo.

The only problem is that people are largely agreed on the fact that The Revenant is far from being his finest performance.

It’s a stunning film, and he clearly went through hell to make it, but you spend more time worrying about DiCaprio’s suffering while making the film than about his character’s plight. It’s a shame, as his win would be tainted by the fact that we all know he’s not really winning for that performance – he’s winning because he’s due a win.

Here are the performances that we think he really deserved an Oscar for.

1. What’s Eating Gilbert Grape?

In his first nomination, DiCaprio was recognised for his portrayal of Johnny Depp’s ‘developmentally disabled’ brother Arnie. He portrayed Arnie with accuracy and without condescension.

DiCaprio’s Arnie is more than his disability – he’s infuriating, lively, loving, funny and achingly vulnerable. It’s one of the best on-screen portrayals of the disorder that, today, we would recognise as either a chromosome disorder or autism.

2. The Aviator

DiCaprio’s next nomination came for his definitive portrayal of Howard Hughes. He’s become something of a pro at playing characters who go from having it all to losing their grip (see also: Shutter Island, Revolutionary Road, Inception), and it still seems strange that he somehow didn’t win this one.

3. Catch Me If You Can

I have a real soft-spot for DiCaprio in a lighter mood. Catch Me If You Can is an underrated film, with two seriously underrated central performances from DiCaprio and Tom Hanks. DiCaprio really shines as the boyish professional liar who schemes his way to the top while trying not to hurt anyone along the way.

DiCaprio holds the balance between confidence and vulnerability perfectly.

4. The Wolf of Wall Street

2014 was a tough Oscar year, as Leo found himself up against both HIV and slavery – both far more award-friendly topics than super-rich, morally bankrupt addicts. But in any other year, his enormously engaging – but slightly terrifying – performance would have been unbeatable.

He gladly surrendered all dignity for this movie and finally got a chance to give a proper airing to the comedy skills that he’d hinted at in other performances.

5. Titanic

The film won just about every award going except acting ones. Kate Winslet was at least nominated, but DiCaprio didn’t get a look-in. But has DiCaprio ever been more likeable and charismatic than in this role? He played Jack Dawson in the classic matinee idol style – which is harder to pull off than you might think. And did anyone not cry when he died?

6. The Departed

He was overlooked for this film, largely because no awards academy could work out whether he should be in the lead or supporting actor category, given that this was an ensemble film.

In a movie hailed for great performances across the board, DiCaprio is the one who truly shines as the paranoid, gradually disintegrating Billy.

7. Django Unchained

Tarantino has a rare talent for coaxing surprising performances out of actors, and seeing DiCaprio as such a repellent villain is quite a shock to the system. He deserved recognition for the famous glass-smashing scene alone, during which he sliced his hand open by accident. He kept the scene going, using his injury to brilliant effect both for himself and the other actors in the scene, all of whom looked frankly terrified.

8. Shutter Island

We won’t spoil the twist for you, but this is the most unbalanced in a long line of unbalanced DiCaprio performances. He plays a US Marshal gradually losing his marbles in a hospital for the criminally insane.

DiCaprio plays the tragedy of someone struggling and failing to adjust to reality better than just about anyone else in Hollywood.

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