Ten Leonardo DiCaprio Films He Should've Also Won an Oscar For

After Leo’s long-overdue Oscar win, it is only fitting for us to reflect back at his amazing body of work. As someone who has watched every single one of his films (yes, since Critters 3 in 1991), I’ve managed to come up with a top 10 list of his films:

1. What’s Eating Gilbert Grape (1993)
This has to be my favorite Leo film of all time. In What’s Eating Gilbert Grape, Leo plays the amiable Arnie Grape, the mentally impaired brother of Gilbert Grape (played by Johnny Depp). His performance in this is absolutely heartwarming, and was so impressive that many thought that his character was played by someone who was actually mentally-ill. In fact, his role in this film garnered him his very first Oscar nomination at a young age of 20.

2. The Departed (2006)
Directed by the renowned Martin Scorcese, The Departed is one of the best crime films I have ever watched. In this, Leo plays Billy Costigan, a young undercover cop who gets assigned the dangerous task of infiltrating a mafia. The film is known for having a star-studded cast: Jack Nicholson, Mark Wahlberg, Matt Damon, Alec Baldwin, and Vera Farmiga. It was so critically acclaimed that it managed to receive four Oscars at the 79th Academy Awards: Best Picture, Best Director (for Scorcese), Best Adapted Screenplay, and Best Film Editing.

3. Catch Me If You Can (2002)
Catch Me If You Can is one of Leo’s more light-hearted films. Both clever and comedic, this film is based on the true story of Frank Abagnale Jr., a man who becomes an expert con-man by posing as a PanAm pilot, a Georgia doctor, and a Louisiana prosecutor. The film also stars Tom Hanks as Carl Hanratty, an FBI agent who attempts to track the fraudulent behavior of Frank, and is directed by the celebrated Steven Spielberg.

4. The Wolf of Wall Street (2013)
The Wolf of Wall Street is Leo’s fifth collaboration with director Martin Scorcese and tells the real-life story of Jordan Belfort, a former Wall-Street stockbroker who made millions of dollars through countless scams and acts of deception. The film depicts a life of excess, corruption, and hedonistic behavior; at its crux, it is a cautionary tale laced with elements of black comedy. The film also features Margot Robbie, as well as the hilarious Jonah Hill.

5. The Basketball Diaries (1995)
The Basketball Diaries is definitely a classic Leo film. Filmed just before “Leomania” exploded, it tells the story of Jim Carroll (played by Leo), a promising basketball player who descends into heroin addiction through the influence of his friends. The film is essentially a coming of age film, and explores themes of peer pressure, crime, and drug addiction. It is based off the autobiographical novel of Jim Carroll.

6. The Aviator (2004)
The Aviator tells the compelling story of Howard Hughes, a real-life aviation pioneer played by Leo. The film chronicles the life of Hughes from the 1920s to the 1940s, a time in which Hughes became both a renowned film maker and aviator. His character, however, is also severely afflicted by OCD and, as the film goes on, we begin to see Hughes’ character descend into a state of instability. The film also features Cate Blanchett as Katherine Hepburn and Kate Beckinsale as Ava Gardner - both of whom were Hughes’ real-life love interests. The film was critically-acclaimed, and managed to garner 11 Oscar nominations, most notably for Best Actor (for Leo), Best Picture, and Best Director.

7. Inception (2010)
In Inception, Leo plays the role of a spy who is able to steal information by infiltrating the subconscious of his targets - specifically through their dreams. The film’s concept is one that is original and captivating; in fact, it is so mind-boggling that it takes several watches to truly appreciate its intricate plot. This film marks Leo’s collaboration with another amazing director, Christopher Nolan, as well as an amazing cast, which features Joseph Gordon Levitt, Marion Cotillard, Ellen Page, Tom Hardy, Michael Caine, Cillian murphy, and Ken Watanabe.

8. Django Unchained (2012)
Directed by Quentin Tarantino, Django Unchained is set in the Old West, a time in which the slave trade was still ongoing. In this, Leo plays the role of Monsieur Calvin J. Candie, a notorious slave-owner, who takes pleasure in watching his slaves fight to the death. This is a classic Tarantino film: action-packed, and filled with memorable punchlines and black comedy. It also stars Jamie Foxx, Christoph Waltz, Kerry Washington, and Samuel L. Jackson. Albeit its controversial nature, it was well-received among critics and was nominated for five Academy Awards.

9. The Great Gatsby (2013)
The Great Gatsby is Leo’s second collaboration with director Baz Luhrmann (the first being Romeo + Juliet - another must-watch Leo film). Based on the classic novel by F. Scott Fitzergald, The Great Gatsby revolves around the mysterious and charming Jay Gatsby, played by Leo. The film is set in the “Roaring Twenties” - an era of glamor and extravagance; thus, it is no surprise that the cinematography in this film is absolutely beautiful.

10. Shutter Island (2010)
Shutter Island is a psychological thriller film, based off Dennis Lehane’s novel of the same name. Leo stars as U.S. Marshall Teddy Daniels, who arrives at an eerie mental institution to investigate a case of a missing patient. The film takes on a darker tone, and remains suspenseful throughout. The highlight of this film is most definitely the ending, which leaves the audience in a state of perplexity and with an urgent desire to re-watch the film.