Leonardo DiCaprio has been in more than 30 films, and while he’s finally won an Oscar for his role in The Revenant, he’s done at least five other roles where he deserved it more.

‘Catch Me if You Can’ – 2002

revenant catch me if you can

Role: Frank Abagnale Jr.

Back in 2002, when DiCaprio was nearing 30 years old, he played the baby-faced Frank Jr. in Catch Me if You Can alongside Tom Hanks. It was not only a great film, but we see Leo basically go from what looks like a 15-year-old to a 30-year-old in the span of two hours.

He plays so many different characters in the film, and held his own opposite Tom Hanks, which proved to me that he was more than capable of continuing his successful career in Hollywood.

He showed a lot more range in this film than he ever did in The Revenant, and the ability to believably act and look so young was inspiring. I think it was some of his best work, and easily better than his role in The Revenant.

‘The Departed’ – 2006

revenant the departed

Role: Billy Costigan

Possibly Leo’s best role ever, he plays the complex Billy Costigan, who is an undercover cop trying to identify a mole in the police department while infiltrating an Irish gang in South Boston.

As Billy, Leo goes up against possibly the deadliest villain Jack Nicholson has ever portrayed, and together they perform one of the most excellent scenes in the history of film.

Leo and Jack sit at a table in a bar, as Nicholson’s character tries to determine whether he can trust Leo’s character or not. The tension that is built up, in no small part by Leo, is incredibly believable. This role showed Leo at his best, and while the film took home four Oscars, including Best Picture, Leo was left empty handed.

‘Django Unchained’ – 2012

revenant django unchained

Role: Calvin Candie

In Django Unchained, Leo plays Calvin Candie, who is a Mississippi slave owner. Possibly the most detestable role he’ll ever play, Leo finally portrays a villain that gives even his biggest fans chills.

Leo portrays Calvin Candie with pure hatred; he’s vile, and it’s possibly the farthest from himself that he’s ever portrayed on film. His racism and violent temper prove too much for even himself, as he sliced open his hand during one powerful scene.

DiCaprio scares everyone in the film, except possibly Django, and the character doesn’t really have a lot of time on screen compared to the rest of the cast. He certainly deserved recognition for his role as Mr. Candie, and without a doubt proved to be a formidable force in Hollywood after the portrayal of the vile slave owner.

‘Gangs of New York’ – 2002

revenant gangs of new york

Role: Amsterdam Vallon

Gangs of New York takes place in 1863, where Leo portrays Amsterdam Vallon, who returns to the Five Points area of New York City seeking revenge against Bill the Butcher, his father’s killer.

Not only is the film unbelievable, and quite possibly our best look at ‘old’ New York, it featured Leo’s incredible portrayal of Amsterdam Vallon, who flirts with death in every scene as he gets close to his father’s killer, played by Daniel Day-Lewis.

The role is breathtaking, and seeing Leo’s reactions to Daniel Day-Lewis’ bizarre behavior as the Butcher is quite simply amazing. Leo deserved a win for this role, and it came out the same year as his amazing role in Catch Me if You Can.

‘The Aviator’ – 2004

revenant the aviator

Role: Howard Hughes

The Aviator is… long, but for anyone who sat through the entire epic, it’s easy to understand just how incredible DiCaprio was as the reclusive real-life billionaire Howard Hughes.

As Howard, Leo starts as a young man trying to find his way after inheriting millions when his parents pass away, and DiCaprio’s ability to portray his hatred for all the bullying he receives from “old money” in Hollywood.

Taking his character from a young millionaire, to the dirty reclusive-billionaire, is nothing short of amazing. He takes on the impossible role of Howard Hughes and makes him believable. He also shows the slow turn of events that reveals the eccentric billionaire’s obsessive–compulsive disorder.

Leo’s ability to show this disorder in such a brilliant way is what proves he deserved recognition back in 2004 at the Academy Awards. It’s difficult to pull off crazy without it being a bit comical, but he nailed the tragic character beautifully.

What role do you think Leonardo DiCaprio deserved an Oscar for more than ‘The Revenant’?

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