5 Reasons why Leonardo Dicaprio hasn't won an Oscar

Luckless Leo: 5 Reasons Dicaprio has yet to bag an Oscar

Amanda Lim

11 Nov 2015

updated the 3 May 2019 à 14:23

His trophy cabinet may be pretty empty, but it doesn’t mean the actor isn’t one of the greats.

1/5
His Good Looks
Since movies like Romeo + Juliet and Titanic, the actor has had to work thrice as hard to pick good roles in good movies to escape the notion that he’s “just a pretty face”. Like Johnny Depp, Leo’s teen heartthrob status means he has to try a whole lot harder to impress the nitpicky Academy.
2/5
Bad Timing
You gotta admit, sometimes these things really boil down to luck. Time and time again the actor has been up against fellow nominees (Forest Whitaker, Jamie Foxx, Matthew McConaughey) that just so happen to be having a real big career defining moment.
3/5
His roles aren’t transformative enough
Most Best Actor winners go through sacrifices to nab the coveted award. Colin Firth had to stutter, Jamie Foxx went “blind”, and Eddie Redmayne turned into Stephen Hawking. As much as DiCaprio commits to his roles, he still comes off screen like Leo Dicaprio playing a role.
4/5
His films aren’t “weighty”
It’s no secret that the Academy is partial to films that are culturally or socially significant. At the 86^th Academy Awards for example. The Wolf of Wall Street, a raunchy drama-comedy about a hedonistic broker, was up against movies like 12 Years A Slave and Dallas Buyers Club. Even with the backing of famous directors like Martin Scorsese, Leo’s movies are just blockbusters compared to such heavy films.
5/5
The Academy loves a story
As much as The Academy Awards is about honouring talent, at the end of the day, it is a money-generating business. Ratings go up and papers sell when there’s a good story. It seems like the story of pretty boy Leo Dicaprio just hasn’t been compelling enough for the pressroom. #truth

Leonardo DiCaprio may be ringing in the big four-O today, but he shows no signs of slowing down in his career. The actor’s next big movie, The Revenant, is due to be released this Christmas. Like all films starring Dicaprio, this Alejandro Iñárritu movie comes with whispers of an Oscar win for the actor.

Sadly, all that talk has never materialised into an actual award for Dicaprio. Even with dozens of films under his belt that have conquered the box office, the actor has only been nominated four times without a win. Not to mention, some of his critically acclaimed roles have failed to impress the Academy for a nomination.

His predicament is a head-scratcher, seeing that it is evident that Leo does have the talent (What’s Eating Gilbert Grape) and the commitment (The Wolf of Wall Street) that makes a great actor. Always the bridesmaid and never the Oscar bride, DiCaprio may very well be one of the most under appreciated talents in Hollywood.

We round up the five reasons why Leo Dicaprio hasn’t managed to score an Oscar win, yet.

Amanda Lim

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