It is a universal truth that one of the greatest actors of our time is Leonardo DiCaprio. During his career spanning over twenty years, DiCaprio has delivered many incredible performances. Whether he is playing a star-crossed lover in Romeo and Juliet or an undercover cop in The Departed, or everything else in between, he always puts every ounce of effort into everything he does. The great tragedy of Hollywood is that some stars fade out much too quickly. Fortunately for us, DiCaprio is a star that has burned brightly for over twenty years, and will hopefully continue to shine for twenty more. When reading this list, let us reflect on how it is possible that DiCaprio has never won an Academy Award.
10. Titanic (1997)
In the late 1990s, DiCaprio became known as the next teen heartthrob in Hollywood, partly due to Baz Luhrmann’s adaptation of Romeo and Juliet from the year before, but mostly because of James Cameron’s 1997 classic, Titanic. This film creates a fictionalized account of the 1912 sinking of the RMS Titanic. The film tells the story of working class Jack Dawson who, after winning his way onto the Titanic’s maiden voyage, falls in love with the upper class and engaged Rose DeWitt Bukater (played by Kate Winslet). The best part of DiCaprio’s performance is that he does not overplay the epic romance. A trap that many romantic films fall into is that the romance is played to the point where it is no longer believable. DiCaprio and Winslet portray their character’s love story authentically, without going overboard. This is a film that will definitely go down in history as one of the greatest of all time, which may cause some to wonder why it is so low on this list. Even though this may have been DiCaprio’s greatest performance at the time, looking objectively at his career, many of his more recent performances are even better. Regardless of this, Titanic still deserves a place on this list because it is the film that arguably launched DiCaprio’s career.
9. The Wolf of Wall Street (2013)
The Wolf of Wall Street marks DiCaprio’s fifth film collaboration with director Martin Scorsese, where he depicts how real-life figure Jordan Belfort became his own worst enemy. The film tells the story of the creation of Belfort’s company Stratton Oakmont and the company’s greed and corruption on Wall Street, which leads to Belfort’s arrest, ending his days on Wall Street. This film is unlike anything DiCaprio has ever done before. His character is funny and charismatic, but also disturbing and unlikeable all at the same time. Part of you wants to see DiCaprio overcome the obstacles he faces and come out on top, but you also can’t help but feel immense joy when he finally gets what is coming to him. It is this role that provided DiCaprio with his latest snub at the Academy Awards.
8. Revolutionary Road (2008)
Ten years after their journey together in Titanic, DiCaprio and Winslet reunited in Sam Mendes’ 2008 film Revolutionary Road, based on the 1961 novel of the same name by Richard Yates. This heartbreaking film tells the story of Frank and April Wheeler, who move to the suburbs of Connecticut to settle down and have a family in the 1950s. While they and their two children appear to the outside world as a happy family, all is not as it seems. Frank works long hours at a job he hates and April has grown tired of the monotonous life of a housewife and resents allowing her family to conform to society. DiCaprio does a wonderful job at depicting Frank’s frustration and confusion with his life and how he managed to drift so far away from the dreams he once had. The most remarkable thing about this film is that DiCaprio and Winslet were able to reunite as love interests, but completely remove themselves from who they played in Titanic. After a certain point in this film, you forget about them as Jack and Rose and begin to only see them as Frank and April.
7. The Great Gatsby (2013)
In 2013, DiCaprio reunited with Baz Luhrmann (who also directed Romeo and Juliet) to make a film adaptation of The Great Gatsby, F. Scott Fitzgerald’s 1925 novel of the same name. DiCaprio plays Jay Gatsby, a millionaire bachelor of the Roaring Twenties whose only desire in life is to reunite with his long-lost love, Daisy Buchanan. Because The Great Gatsby is one of my favorite novels of all time, I had high hopes for this film, and DiCaprio certainly did not disappoint. He was extremely faithful to Gatsby’s hopefulness and ambition. His performance is heartbreaking because you want to see Gatsby succeed (even though my friends and I agree that he is too good for Daisy), but know that he is ultimately too ambitious for his own good.
6. Django Unchained (2012)
After the 1990s were over, DiCaprio was finally able to shed his teenage heartthrob label by taking on more mature films and roles. After this point, it seems that he made a rule for himself to not play roles that could be boiled down to being an archetypal character, like the love interest or the main character’s best friend. However, in 2012, he broke this rule in Quentin Tarantino’s western film Django Unchained. DiCaprio plays Calvin Candie, a plantation owner in Mississippi who is in possession of Broomhilda (played by Kerry Washington), the wife of Jamie Foxx’s Django. One of the most interesting things about this film is that we have never seen DiCaprio play a character that is strictly a villain, and yet he did it very well. In all of the characters that DiCaprio has played, there is always something that gives them a certain degree of likability. But, in this film, there is nothing likeable about his character. After you watch this film for the first time, you walk away feeling shocked that such a wonderful person like DiCaprio could succeed in playing such a despicable character. Even though he does not have much screen time in this film, DiCaprio was still able to leave his mark as a dastardly villain, showcasing his remarkable acting abilities.
5. What’s Eating Gilbert Grape (1993)
In What’s Eating Gilbert Grape, DiCaprio delivered one of his most touching roles to date. In this film, he played Arnie Grape, the soon to be eighteen-year-old with a developmental disability, requiring that he is monitored and cared for around the clock by his older brother Gilbert (played by Johnny Depp). The most beautiful thing about this performance is that Arnie is a character that could have very easily been overplayed and made into a stereotype. DiCaprio was able to tap into the sweetness and innocence of this character and play it very genuinely. This performance makes you realize that Arnie just wants acceptance and love from those around him. In one of the most beautiful, and I think underrated, scenes, the family is planning Arnie’s birthday party and, upon his asking what his job his, is disappointed to learn that his only job is to show up. This is supplemented by the scenes of Arnie’s obsession and dedication to climbing to the top of the town’s water tower. Separately, these scenes do not mean much, but together, they highlight DiCaprio’s brilliance in showing that, despite Arnie’s disability, he wants to be able to accomplish something on his own like everyone else can.
4. The Aviator (2004)
In this film, DiCaprio portrays Howard Hughes, an American director and aviator. This film chronicles Hughes’ career in film and later progression into the world of aviation, where he builds new plane models and sets many world records for air speed. The foundation of this film, however, is Hughes’ struggle and eventual mental breakdown from persisting paranoia, obsessive-compulsive disorder (OCD), and depression. DiCaprio managed to strip away all of the glorification and misrepresentation that can come with depicting mental illness and shows the tragedy of Hughes’ struggles and how they were detrimental to his career.
3. Inception (2010)
In one of his most interesting and complex films to date, DiCaprio plays professional thief Dom Cobb in Inception. Cobb is not just any thief; he specializes in the theft of secrets through dream infiltration. Cobb signs up for one last job to infiltrate the mind of a man about to inherit his father’s company in exchange for getting home to his children, all while being haunted by his past. DiCaprio does a spectacular job of depicting Cobb’s struggles battling unforeseen opposition in his victim’s mind, while also battling demons in his own mind. This is a film that needs to be seen two or three times to be fully understood, but is definitely worth it.
2. The Revenant (2015)
In his most recent film, DiCaprio plays Hugh Glass, a real life fur trapper and frontiersman from the 1820s. The film follows Glass as he is severely mauled by a bear, wronged by his men, and struggles through the harsh Montana and South Dakota winter as he tries to get revenge on the man who murdered his son. The most remarkable thing about this film is that DiCaprio only had, by my estimation, less than ten minutes of dialogue in a two-and-a-half-hour film and still managed to give one of the best performances of his career. Without saying much of anything, DiCaprio is able to portray Glass’ dramatic, and often difficult to watch, hardships and intense desire to avenge the death of his son. If DiCaprio does not win his long deserved Oscar for this film, then all hope of him ever winning one will probably be lost.
1. Shutter Island (2010)
My favorite performance of DiCaprio’s appears in one of my favorite films of all time: Shutter Island. In his fourth collaboration with Martin Scorsese, DiCaprio plays Edward Daniels, a US Marshall sent to Ashecliffe Hospital on Shutter Island to investigate the disappearance of a patient named Rachel Solando. As is true in much of DiCaprio’s best work, Daniels struggles to do his job while simultaneously battling with his own mind. As the film unravels, DiCaprio expertly depicts Daniels’ confusion as he descends into insanity upon the realization that nothing about the Solando case or the island makes any sense. DiCaprio and Scorsese take the viewer on a confusing and complex journey with a shocking and unforeseeable ending.