Top Ten Leonardo DiCaprio Roles

Alan Thicke: “We had the sense then that nothing was ever going to stop him. He just lit up the place.”

If the prophecy proves true, Leonardo DiCaprio will finally earn that coveted Academy Award for his marathon performance in The Revenant. Leo bailed on babes and the beach to commit to Alejandro Gonzalez’s survival film that involves munching raw bison liver and sleeping in animal carcasses in the brisk conditions of Calgary.

Throughout the three decades of his film career, he has won 34 awards from 137 nominations that include two Golden Globes and five snubs from the Academy. Since he was removed from a television series for being too disruptive at 5-years-old, he’s been a Teen Beat heartthrob, commander of Hollywood’s $20 million club and the front runner of the Dadbod craze. He’s also been the muse of many directors like Steven Spielberg, Ridley Scott, Quentin Tarantino and most notably, Martin Scorsese.

Let’s remember those moments that were otherwise overlooked by the glorified stamp of approval from the Academy Of Motion Picture Arts and Sciences.


Transforming himself into Howard Hughes shed the post-Titanic heartthrob label with this establishment of adulthood. This was his Bar Mitzvah, if you will. With his comrade Scorsese, they brought us into the Golden Age of Hollywood with a portrayal of an eccentric-billionaire that became an OCD-hermit. As Hughes works on the delirious film Hell’s Angels and battles political figures, while building the legendary Spruce Goose he begins to descend into OCD obsession. DiCaprio notably spent much time in conversation with experts, observing those afflicted with the condition to embody the mental process of germaphobes. He’s a devoted, versatile definition of the oft-overused “tour-de-force performance” and this can be pointed to as the initiator of the Academy Award snub obsession.


He is the son of an abusive stepfather, portrayed by Scorsese’s other son – Robert De Niro. His most notable credit at this point was Growing Pains and then he went one-on-one with Jake La Motta.


It was also released on the same week as the first of five (and counting) films that teamed him with Scorsese, Gangs Of New York, but this performance as a real-life con man that earned more attention. He’s a smart teenager on the run from Tom Hanks’ FBI agent Carl Hanratty. That’s it! That’s all we say.


This finally earned Scorsese his elusive Oscar, but DiCaprio was overlooked and applauded for his Blood Diamond performance instead. Quit playing games with him, Oscar! He is a man who almost lost his identity. We’ve all been there, haven’t we?


Calvin Candie is a charismatic slave-owner. Another character from the demented heart of Tarantino. DiCaprio provides a genuine likeability to a pathetic monster. He truly deserved more recognition for this psychotic charisma. Recount!


Christopher Nolan was riding the waves of Batman franchise success when he penned and directed this offbeat picture that places DiCaprio in the forefront as a tormented man, struggling with his demons. What sounds like a classic recipe for DiCaprio has never been this paranoid. Dreams!


Much hyped for the reunion with his Titanic co-star Kate Winslet, this was the pageturner of DiCaprio’s bad-love period of films. This adaption of Yates’ novel documents suburban domestic turmoil with an emotional chaos between two people trapped in their own environment. “I found Frank immediately detestable,” DiCaprio explained to a screening audience, “but then there’s this element to him that you find so entirely sympathetic, because he’s trying to make a happy home.”


DiCaprio and Scorsese, again! Obsession, again! They teamed up for a psychological, mind-bender that is all good except for the twist ending. Leo’s never been so vulnerable, as he is playing an US Marshal investigator at the appearance of a cryptic inmate on a creepy island insane asylum. He strips his character apart in a bravado that is reminiscent of Jimmy Stewart or Cary Grant in their Hitchcock collabos.


His first Academy Award nomination wasn’t a stunt. He was a powerfully complicated boy named Arnie, messy and lovable with chemistry alongside Johnny Depp as a dysfunctional family in Iowa. He was very young, which makes it all that more impressive that he was able to delicately sense balance of controlled spontaneity and tough realism.


Scorsese and DiCaprio. They come together again for an exposure of Jordan Belfort’s lifestyle as a corrupt Wall Street stockbroker. It was a friend to controversy for glorifying the perks of the millionaire lifestyle, rather than his gratuitous swindling. It is a drug-fueled engine with dark comedic overtones as masterfully exposed in the Marx Brothers-esque Quaalude scene.

Think we missed something on the list? Let us know your favorite role in the comments below.