It’s an undeniable fact that Leonardo DiCaprio is one of the best actors ever. Which raises the question: Why did it take so long for him to finally win an Academy Award? Sure, there were some serious stinkers in there, but that doesn’t let the Academy off the hook. Proudly willing to be the standard bearers, loudly shouting “Give Leo an Oscar!” as we charge the ramparts of the Academy, here’s the definitive and undeniable list of every movie prior to The Revenant that should have earned Leonardo DiCaprio an Oscar and how you can stream them right now on your NVIDIA SHIELD Android TV!
Based on the life of Jordan Belfort, The Wolf of Wall Street follows our main character, played expertly by Leonardo DiCaprio, as he takes an entry-level job at a Wall Street brokerage firm in 1987. Still in his 20s our would-be “protagonist” founds his own firm and before long makes a mint largely by defrauding wealthy investors out of their not-necessarily hard-earned millions. Being the ‘80s and ‘90s our eclectic band falls into the expected world of sex and drugs as the SEC and FBI close in on them. Watch it on Epix, Hulu, or Google Play.
Directed by Quentin Tarantino, Django Unchained takes place just before the start of the Civil War and follows Django, a slave who is played by Jamie Foxx, who finds himself freed from bondage by a quirky German bounty hunter, played by Christoph Waltz, who is searching for the ruthless Brittle brothers. The two become fast friends and continue to hunt the most-wanted criminals in the South as they make their way to DiCaprio’s Candyland plantation to rescue Django’s wife who is still being kept in bondage. As we’ve all come to expect from a Tarantino film, Django Unchained is incredibly violent. Also, aside from Leo, the entire cast was amazing Google Play.
In my defense I first saw Inception on a transatlantic flight from London’s Heathrow Airport to SFO in San Francisco. Maybe it was exhaustion or the free in-flight drinks but I loved it so much that I immediately watched it again. To this day, it’s still one of my favorite DiCaprio films. In it DiCaprio plays a thief named Dom Cobb who is able to enter people's dreams and steal their secrets. While this skill is great for making money, especially in the world of corporate espionage it isn’t without its costs and Leo’s character has paid dearly for it. Could this one last job give him what he wants more than anything? A chance at redemption? Find out on Google Play.
Loosely based on the life and crimes of notorious Boston crime lord James "Whitey" Bulger, The Departed follows South Boston cop Billy Costigan (Leonardo DiCaprio) as he goes undercover to infiltrate the organization. With an ensemble cast that includes Jack Nicholson as the crime boss, Martin Sheen as the police captain, Matt Damon as a well… (I won’t spoil it for you) and Mark Wahlberg basically playing the version of Mark Wahlberg that we’ve seen in every other movie. And also love in every one of those movies. The Departed is a gritty tale of crime, corruption, deception and revenge. It’s a must see. Watch it on Google Play or HBO Now.
Gangs of New York is one of those amazing movies that’s about so many different things: immigration, race relations, the Civil War, the history of NYC politics, the list goes on. Yet another Martin Scorsese film that perfectly highlights DiCaprio’s genius the movie follows the life of the orphaned Amsterdam Vallon (Leonardo DiCaprio), an Irish immigrant who returns to his childhood neighborhood of New York’s Five Points seeking revenge against his father's killer. With an ensemble cast that includes Liam Neeson, Brendan Gleeson, and Cameron Diaz, Daniel Day-Lewis steals the show as William “Bill the Butcher” Cutting, a powerful nativist (read: anti-immigrant) gang leader. Watch it on Google Play.
The film that put Leonardo DiCaprio on the map, he was actually nominated for a best supporting actor, up against Ralph Fiennes in Schindler's List, John Malkovich’s performance from In the Line of Fire, and Pete Postlethwaite from In the Name of the Father. They all lost to Tommy Lee Jones for his performance in The Fugitive. What's Eating Gilbert Grape follows the life of Gilbert Grape who is played by Johnny Depp. A small-town young man who’s forced to take care of his family while carrying on an affair with an older married woman played by Mary Steenburgen, Leonardo DiCaprio steals the movie as Gilbert’s troubled younger brother Arnie. Be ready to break out the tissues for this one. Google Play.
Honorable mention: Emmy for his uncredited appearance in the Home-Ec Episode of Season 3 of Roseanne as "Darlene’s classmate."
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