Leonardo DiCaprio’s 5 Best Roles That Didn’t Win Him An Oscar

Today is Leonardo DiCaprio’s birthday. And as we are sure he is partying hard somewhere with a crew of about twenty women, we want to honor the celebration with some of his best roles.

These roles, though, are the ones that were impeccable, but not great enough to get him that coveted gold statue.

From a wacked-out coke head millionaire to a diamond-slinging smuggler, DiCaprio has turned in some truly mesmerizing performances.

Want to add some to the list? Feel free to drop some other films into the comments section below.

5. Catch Me If You Can

Catch Me if You Can is one of Steven Spielberg’s most underrated films. It is the perfect blend of cat and mouse, but edged nicely with biting, clever humor. And most of that humor is beautifully executed by Leonardo DiCaprio’s knack for being able to deliver a line that should make us hate him, but instead it makes us laugh and want to be on his side.

DiCaprio did get a Golden Globe nomination for the role of Frank Abagnale, Jr. (a real-life person and a true story), but The Academy did not feel the same way. 

Do you “concur” that DiCaprio should have taken home an Oscar for this role? 

4. The Wolf Of Wall Street

Where do we even begin with The Wolf of Wall Street? Martin Scorsese’s ‘excess is death’ dramedy is a pulse-pounding exploration of the human psyche… on a lot of coke. Leonardo DiCaprio was born for the role of Jordan Belfort – a real-life broker who was a drug-fueled machine for partying and overall debauchery. 

DiCaprio was nominated for an Oscar for Best Leading Actor, but fell short. He was also nominated for Best Picture for producing the film alongside Scorsese.

DiCaprio breaks the fourth wall the entire movie, guiding us on a journey laced with ludes and soaked in champagne. The role of Jordan Belfort needed pure electricity, and boy did he bring it.

3. The Basketball Diaries

The Basketball Diaries is a movie that is not for kids whatsoever. It depicts the dark depths of drug addiction and what can come as a result (yes, some of the scenes are hard to watch). DiCaprio really turns on the acting jets in one of his first big early roles. He successfully makes us believe he is a teen who cannot came out of the pit of heroin addiction. 

DiCaprio’s younger roles really built some sturdy tentpoles for his career – not only was he talented at that age, but he chose his dramatic roles wisely. The Basketball Diaries was a smart decision.

2. Blood Diamond

People seem to forget that Blood Diamond even exists. It does. And it is a damn good film. The pacing is a bit shaky, but the acting from DiCaprio is brilliant – specifically the accent he adopts for the role. 

DiCaprio’s South African accent is piercingly good and is almost addictive to listen to. The below scene should be all the reason for an Oscar alone, granted he was only nominated for one for this role. 

[H/T YouTube, krda0702]

1. What’s Eating Gilbert Grape

DiCaprio’s first Oscar nomination — for Best Supporting Actor — was for What’s Eating Gilbert Grape, and his performance still stands the test of time. 

He tackles the role with pure dedication to depicting Arnie as a mentally challenged brother who sees the world in its purest forms. He feels pain so deeply. He feels joy that overflows him when he plays hide and seek. DiCaprio took this approach and turned in the best performance of his career.