10 Best Leonardo DiCaprio Roles That Deserved An Oscar

1. Jack Dawson in “Titanic” (1997)


Leonardo’s most famous role was Jack Dawson in James Cameron’s “Titanic,” the critically acclaimed and one of the highest grossing box offices in the world.

Leonardo made every woman fall in love with him in the role of Jack, a big dreamer and charming romantic that still captivates female audience members to this day.

2. Romeo in “Romeo + Juliet” (1996)


Leonardo’s first romantic role on screen and it couldn’t have fit the handsome youth better. The movie itself had mixed reviews, with some people calling it an insult to Shakespeare, and Roger Ebert calling it a “dumb-down version of one of the greatest love stories ever told.”

A lot of people didn’t like seeing the play set in modern times with the original dialogue mostly in tact. Young Leonardo, however, engrossed himself in the role and made a modern day Romeo very plausible.

3. Cobb in “Inception” (2010)


Leonardo plays a sympathetic character in this brilliant sci-fi thriller who must battle his mental demons or jeopardize the safety of his crew as they dive deeper into an unsuspecting man’s subconscious.

Leonardo proved with this role that he was more than just a pretty face – he is also an accomplished actor.

4. Arnie Grape in “What’s Eating Gilbert Grape” (1993)


In one of his first major screen roles, Leonardo took on the challenge of playing a mentally disabled boy named Arnie Grape.

“What’s Eating Gilbert Grape” is a critically acclaimed and beloved drama that also stars a young Johnny Depp. Arnie Grape is mischievous, curious, playful, and loves his older brother Gilbert (Depp).

Some people found Leonardo’s acting so convincing that they believed Leonardo actually was mentally disabled, landing him his first Oscar Award Nomination.

5. Teddy Daniels in “Shutter Island” (2010)


“Shutter Island” is a well done psychological thriller that will keep you guessing until the very end. What better person to follow down this rabbit hole than Leonardo.

The story follows Teddy Daniels investigating the disappearance of a patient of a high security prison for the criminally insane. Every answer Daniels gets leads to more questions and memorable moments with one of our favorite actors.

6. Calvin Candie in “Django Unchained” (2012)


This was a very different sort of role for Leonardo. He has abandoned romantic roles and has done subtle and sympathetic characters for most of his career, until now.

Calvin Candie is a plantation owner in this Tarantino version of a spaghetti western film, and he isn’t what anyone would call subtle.

Leonardo takes the chance to be out of his comfort zone and puts his all into this insane and unpredictable character, even going as far as cutting his hand with a smashed glass while still remaining in character. Calvin Candie is a fun character to watch and fear at the same time.

7. Frank Abagnale Jr. in “Catch Me If You Can” (2002)


In this critically acclaimed movie, Leonardo plays real life criminal Frank Abagnale Jr. who managed to dupe everyone before he even turned twenty.

The way his character uses his confidence and intelligence on people makes him fascinating to watch and we end up cheering for him as he breaks the law and tricks Tom Hanks.

When he does end up getting caught and has to face the consequences, you realize you forgot that he was just a kid all along.

8. J. Edgar Hoover in “J. Edgar” (2011)


While the film itself wasn’t very successful critically, it was advertised as a movie that would change the way people looked at Hoover, but it didn’t deliver.

The film didn’t portray Hoover in a bad or untrue light. In fact, Leonardo was praised for his upstanding performance. The movie was considered boring by most, but worth viewing at least once for Leonardo’s acting abilities.

9. Jay Gatsby in “The Great Gatsby” (2013)


It is obvious from watching this film that Leonardo is a fan of the original novel by Fitzgerald. He was quoted as saying “Gatsby is a great tragedy”.

Most critics were split on the movie itself, but loved Leonardo’s portrayal of the mysterious, lonely, hopeful, and great Jay Gatsby.

10. Jordan Belfort in “The Wolf of Wall Street” (2013)


Jordan Belfort has been described by critics as “Jay Gatsby’s evil twin.” They couldn’t be more right. Jordan Belfort is Gatsby, if Gatsby had been more greedy and high on cocaine. Leonardo is obviously having fun taking up roles of loud, insane, and anti-hero characters.

Based on the true story of the infamous Wall Street criminal by the same name, Leonardo uses his untapped hyperactive and sex driven side of himself and puts it into this role that has the audience cheering for him as he dives deeper into the dark side of achieving the American Dream.

The Academy should just give him his Oscar already.