7 Roles Played By Leonardo DiCaprio That Should Have Won Him An Oscar

Leonardo DiCaprio is one of those few actors who can not only do justice to any role, but also – let’s face it – does not fall short in the looks department. I mean, will you look at those baby blues? *swoon*

Though he has been nominated for an Oscar, the golden statue has evaded his hands for quite a while now. And that too, with such stellar performances in his kitty. While other actors are busy boasting about themselves to anybody with an ear *cough* Sonam Kapoor *cough*, Leonardo DiCaprio is busy doing what he does best- being awesome.

All of us, while watching one of his movies, has definitely thought : “C’mon, give Leo an Oscar already!” Here are just a few roles that he has essayed brilliantly – for which he should have been awarded a crown, a kiss on the cheek, and that coveted Oscar statue as well!

1. What’s Eating Gilbert Grape

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In this small-town drama, Leonardo DiCaprio plays Arnie Grape, a boy with a developmental disability. He was nominated in the Best Supporting Actor category at the Academy Awards, aka the Oscars.

He has given a phenomenal performance in this film, and considering the fact that playing a mentally handicapped boy at the age of 14 must have been quite challenging (meaning, most actors get into such serious roles later in their career), his performance is something worth considering.


2. The Aviator

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What do you get when Martin Scorsese and Leonardo DiCaprio work together? An overwhelming number of Oscar nominations. 11 Academy Award nominations. Yep. 11. This film went on to win 5 Oscars, including Best Supporting Actress for the talented Cate Blanchett. In this biographical film, Leo portrayed Howard Hughes, who was an aviator, aerospace engineer, inventor, filmmaker and philanthropist.

He suffered from obsessive-compulsive disorder (OCD), and in order to portray that, DiCaprio worked closely with Dr. Jeffrey Schwartz, Ph.D. of UCLA to portray the most accurate depiction of it. At the time when Hughes was suffering, there was no psychiatric definition for what ailed him. Instead of receiving proper treatment, Hughes was forced to hide his stigmatized compulsions. His disorder began to conflict with everyday functioning and eventually destroyed his once-successful career.

Leonardo DiCaprio dedicated hundreds of hours of work to portray Howard Hughes’ unique case of OCD on screen. Apart from doing his research on Hughes, DiCaprio met with people suffering from OCD. In particular, he focused on the way some individuals would wash their hands, later inspiring the scene in which he cuts himself scrubbing in the bathroom.

Though he was nominated for the Best Performance by an Actor in a Leading Role category, he did not take the trophy home that night.


3. Django Unchained

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As if a film with Leonardo DiCaprio in it wasn’t enough, Django Unchained is directed by Quentin Tarantino. The film was a major critical and commercial success and was nominated for several film industry awards, including five Academy Awards, and grossed over $425 million worldwide. DiCaprio plays a cruel slave owner named Calvin Candie, calling him “the most deplorable human being I’ve ever read in a screenplay in my life”.

One of the most famous scenes in the movie? When Leo cut his hand while the cameras were rolling and kept moving through the scene, never breaking character. His real-life bloodied hand made it into the final version of the film. Talk about being dedicated. Is the Academy of Motion Picture Arts and Sciences listening? (which, in case you were wondering, decides the winners)


4. Shutter Island

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Thanks to Martin Scorsese, we have quite a lot of good cinema that needs that old box on top of our neck to be utilized while watching movies. The film is based on Dennis Lehane’s 2003 novel of the same name. Featuring some epic role playing in order to cure Edward “Teddy” Daniels ( SPOILER ALERT!) and quite an unexpected ending (Thanks to Mr Dennis Lehane), this film is a must-watch.

How do these writers come up with such mind-blowing stories? :O

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5. Revolutionary Road

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Leonardo DiCaprio and Kate Winslet are paired once again after Titanic – which is one film that never fails to bring tears to everybody’s eyes. Like Joey Tribbiani says, “Those two only had each other!”

DiCaprio gives a strong performance as the young, troubled husband Frank Wheeler, who’s working discontentedly for the same company with which his father spent 30 years. Kate Winslet plays his wife, April Wheeler, who dreams of becoming an actress. Set in the late 1940’s, it is a film noir drama which received generally positive reviews from critics. Roger Ebert of the Chicago Sun-Times gave Revolutionary Road four stars out of four, commending the acting and screenplay and calling the film “so good it is devastating”.


6. Blood Diamond

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In this political war thriller, Leonardo DiCaprio stars as Danny Archer, an ex-mercenary who now makes his living trading diamonds for arms. Leonardo has a South African accent in this movie, which he captured by spending a lot of time with the locals. He received many critical accolades for this performance.

He was nominated for the Best Actor category at the 79th Academy Awards… and I don’t need to finish this sentence.


7. The Wolf Of Wall Street

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Martin Scorsese and Leonardo seem to have this amazing connection that keeps on bringing them together – and we desperately hope that this continues, for they have provided us not only with entertaining cinema, but also with some stupendous work of art.

In this film, Leo stars as Jordan Belfort, a stockbroker in New York City, whose firm Stratton Oakmont engages in rampant corruption and fraud on Wall Street, that ultimately leads to his downfall. Once again, DiCaprio got the nod for an Oscar nomination, but did not win.


He has been nominated for an Oscar 4 times:

  1. 2014:  Best Performance by an Actor in a Leading Role – The Wolf of Wall Street (2013)  
  2. 2007:  Best Performance by an Actor in a Leading Role – Blood Diamond (2006)
  3. 2005:  Best Performance by an Actor in a Leading Role- The Aviator (2004)  
  4. 1994:  Best Actor in a Supporting Role – What’s Eating Gilbert Grape (1993)  

And though every time he was nominated, the internet flooded with a lot of memes…

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So what? He hasn’t won an Oscar. Mistakes happen.

All of us know what a brilliant actor he is, and one fine day, all of us will wake up to this:

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Cover Image Source 1 & 2

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