RANKED! The 10 Best Leonardo DiCaprio Movies Before ‘Once Upon A Time in Hollywood’
Photo: Sony Entertainment
Leonardo DiCaprio has been a household name for well over two decades. Like many of his contemporaries, he has gotten into producing films and advocating for philanthropic causes, namely the issue of climate change. Also like many actors of his caliber, he has won an Academy Award for Best Actor—though only rather recently.
DiCaprio’s skill as an actor is beyond question. His work with generational filmmakers like Steven Spielberg, James Cameron, and especially Martin Scorsese has already become more than just bullet points in the long arc of the film history. Be sure to check out our definitive list of DiCaprio’s 10 best films below.
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10. 'Inception' (2010)
Amidst much praise from audiences for his gritty Batman sequel The Dark Knight, Christopher Nolan delivers one of his surface-level cerebral but otherwise digestible films. Imagine a world where corporate espionage has developed to a metaphysical degree in which some have the technology to enter the dreams of others. They use this ability to use one’s subconscious against them, to implant ideas within them. But this job takes a toll on the minds of these specialists, namely DiCaprio’s character, Cobb, who lost his wife as a result of their occupation and now struggles to distinguish reality from the dream world.
9. 'The Revenant' (2015)
After years of varying degrees of public outcry for this or that role, DiCaprio finally won an Academy Award for Best Actor with Alejandro Innaritu’s The Revenant. Hot off his own Academy Award for Best Director with Birdman, which was directed to give the viewer the impression that they are watching one unbroken shot, Innaritu then took his talents to the untamed wilderness where they shot in only natural light. DiCaprio indeed goes all out in this role, and certainly deserves some degree of recognition.
8. 'Titanic' (1997)
Titanic was, for a decade-plus, the highest-grossing film in American history. This love story was resonated deeply with audiences. DiCaprio and Kate Winslet play passionate, star-crossed lovers from vastly different levels of wealth. More than any other film, it taught us to start taking DiCaprio more seriously as an actor.
7. 'Shutter Island' (2010)
In this Martin Scorsese film, two detectives (DiCaprio and Mark Ruffalo) investigate a postwar mental institution on a rocky New England island. A female patient has disappeared, but the more they look into it, the less anything about the titular island makes sense.
6. 'Catch Me If You Can' (2002)
Catch Me If You Can tells the real-life story of Frank Abagnale Jr., one of the greatest grifters in American history. As a Steven Spielberg film, it of course wrestles with the dissolution of a family and how that impacts DiCaprio's protagonist. Its re-creation of mid-20th century America is wholly impressive. DiCaprio commits to his character more than he had ever before—a path that would eventually lead to the gold standard performances of his career.
5. 'Django Unchained' (2012)
DiCaprio’s commitment to character in Quentin Tarantino’s Django Unchained is well-documented. One particular scene is often alluded to in which he was to slam his hand on a table and, in so doing, accidentally smashed a drinking glass but continued to act through the scene anyway. His cartoonishly tyrannical plantation owner makes for a perfect foil to Jamie Foxx’s own titular freed man out for—entirely justified—revenge.
4. 'Gangs of New York' (2001)
Gangs of New York marks the first of many collaborations between Martin Scorsese and DiCaprio. Based on the book of the same name, Scorsese revives a long-dead pre-Civil War world of early organized crime in the Five Points. There are two warring gangs, one of Irish Catholic immigrants and the other of Protestant nativists. When the leader of the nativists, Bill the Butcher (Daniel Day Lewis) kills the leader of the Irish Catholics (Liam Neeson), his young son (DiCaprio) flees and returns years later to seek revenge. It often gets forgotten among the best of Scorsese’s films but it is wholly worthwhile nonetheless.
3. 'The Aviator' (2004)
Scorsese’s biographical picture about the eccentric filmmaker and mogul Howard Hughes is another of his interesting if not frequently lauded late-period pieces. DiCaprio plays the character in fascinating fashion from his early career to his later struggles with obsessive compulsive disorder and overall life in the public eye. It is a stunning recreation of an era of Hollywood that Scorsese clearly has an affection for, but it would feel incomplete had someone else been given the central role besides DiCaprio.
2. 'The Wolf of Wall Street' (2013)
Never before or after has DiCaprio transformed for a role the way he did for The Wolf of Wall Street. Another masterful biographical picture by Scorsese—a descendant especially of his earlier Goodfellas and Casino—DiCaprio plays Jordan Belfort. Belfort struck it rich in the investment industry by using his natural charisma to mislead damn near everyone around him. DiCaprio spent a great deal of time with the real Belfort and this effort was not in vain. It may very well be one of the best individual performances from anyone in 21st century cinema so far.
1. 'The Departed' (2006)
Upon release, The Departed was widely lauded as Scorsese’s best since Goodfellas 16 years prior. He returns to his hobby horse, his favorite subject, organized crime. Based on the Hong Kong thriller Infernal Affairs but transplanted to Boston, DiCaprio and Matt Damon play opposite roles in the war between the mob and the police. It is a wholly satisfying film with—far from a typical run-of-the-mill remake.