Django Unchained & 5 More Films Leonardo DiCaprio Should Have Won An Oscar For But Didn’t
In light of Leonardo DiCaprio’s most recent Oscar snub for a performance that our very own Simon Gallagher called ‘the most skin crawlingly evil Tarantino creation’, which is incredibly high praise when you remember Tarantino’s cameo in Pulp Fiction… That performance was affecting and entertaining, and DiCaprio’s performance was incredible, especially when you consider that this repugnant character was created by the same actor who brought wholesome, hunky hero Jack to
life in Titanic.
This latest snub has got me reminiscing about an actor who has carried blockbusters, been a conduit between small movies and high returns whilst also being an incredible actor. Just how has this incredible talent, who has been a brilliant representative of Hollywood over the last 20 years, gone without academy recognition?
For people interested in the long version of this I have a 2 ½ hour musical number called ‘LeoW!’ in the works, for those interested in the short game: allow me to give you 5 films that DiCaprio should have won an Oscar for… but didn’t.
5. What's Eating Gilbert Grape (1993)
Handicap: Check!
Story dealing with handicap: Check!
Emotional ending: Check!
The crime he probably committed to put the academy off of his first Oscar Worthy Performance (which he was nominated for in the Best Supporting Actor Category) was being a little too young.
It’s stupid, but it is how the Academy works, it’s also incredibly difficult for a newcomer to win awards in the place of Hollywood legends who regularly get nominated but that can’t detract from his performance.
As mentally disabled Arnie he gives an emotional edge and connection to a film that borders on being hollow… In the good way, Johnny Depp’s Gilbert is disconnected and miserable and Arnie is a part of that but DiCaprio’s sweet natured, happy and thoroughly immersive performance makes the audience root for him and more importantly his brother to find happiness to keep Arnie looked after long after his beloved mother is gone.
Like The Joker in The Dark Knight the supporting character outshines the main character and helps make this movie have the impact it does; and Leo should have been rewarded for this.
Who won instead? Tommy Lee Jones for The Fugitive.
4. The Aviator (2004)

If anything this was more Academy baiting than Gilbert Grape, mental difficulties, a celebrated historical figure and directed by Martin Scorsese this should have bagged Leo his Best Actor Award. It won him a Golden Globe just a few weeks previous and won Cate Blanchett a Best Supporting Actress award for what was probably an inferior turn than
Leo, who encapsulated the role of Howard Hughes and kept him captivating for an incredibly long run time.
You don’t feel it when watching a brilliant movie that probably should have garnered him his win.
Sadly he lost to Jamie Foxx in Ray, which had the advantage of being about a celebrated historical figure, blindness and drug abuse. One point short Leo.
Leo’s turn as sometimes detestable, eventually winning Danny Archer was a great character upheaval piece and an engrossing affair. The many facets of Archer’s personality were explored throughout the average – good Blood Diamond and was the best aspect of Edward Zwick’s epic look at the Sierra Leone Civil War.
DiCaprio breaks type here by adopting the personality of someone who is unlikeable throughout the majority of the film but still allows us to be sympathetic with his plight until the end where we really start to feel and root for him.
This is another case where his performance outshone the film as a whole, anyone who likes this film and doesn’t use his performance as a contributing factor is lying.
Despite being nominated he lost to Forest Whitaker in The Last King of Scotland.

Probably his greatest to date, yet one that didn’t earn him a nomination for reasons none can entirely be sure of, rumours that Jack Nicholson demanded to be considered in the Best Actor in a Leading Role as opposed to supporting which made the academy refuse a lead nomination for anyone from The Departed.
He was also nominated this year for Blood Diamond so that might have put the academy off nominating again.
His performance as Billy Costigan was the most memorable in a film which brought career bests from Matt Damon, Mark Wahlberg and Jack Nicholson as his mental best.
Fraying, internally tortured and constantly on edge his was a whirlwind of a display that helped make this film a true thriller of the crime genre from its incredible opening to its shocking end. The Departed sparked my love for film on an ill day in my early teens and DiCaprio’s performance was the brightest spark of it.
Like Blood Diamond, he lost out to Forest Whitaker in The Last King of Scotland.
Go to the source for #1!source


Cinematic masterpiece I tell you.
ETA: LMAO WHAT @ Rev Road being #1. NO ONE came out of that unscathed.
Edited at 2013-01-12 08:46 pm (UTC)
Edited at 2013-01-12 08:46 pm (UTC)
http://popcornandroses.tumblr.com/p
eta: Joaquin Phoenix should in this though. Well, at least Joaquin gets nominated, so idk.
Edited at 2013-01-12 09:07 pm (UTC)
He was amazing in This Boys Life too.
He's a pedo!
i bet he would've shown up if she were nominated for rev road and he wasn't, even, and the boy never shows up unless nominated.
The Reader was SUCH shit and her performance was SO weak! I don't care what anyone says- that movie was awful.