10. What’s Eating Gilbert Grape (1993)
9. Django Unchained (2012)
Quentin Tarantino’s western, Django Unchained, has all the trademarks of a Tarantino flick—stylistic violence, funny banter, and great music—but it also has one defining factor that only one other Quentin Tarantino movie has going for it—Leonardo DiCaprio. And even though I wouldn't rank Django highly among Tarantino's films, DiCaprio plays such a charming scumbag, that he kind of makes up for the lagging second half of the movie when he isn't in it.
8. Revolutionary Road (2008)
Talk about a real downer! Revolutionary Road is the second time that Leonardo DiCaprio and Kate Winslet would appear in a movie together, and it is absolutely nobody’s fan-fiction about what Jack and Rose from Titanic would have ended up like if Jack had actually lived. In this adaptation from the Richard Yates novel of the same name, Leonardo DiCaprio plays a real son of a bitch who cheats on his wife and fights with her on multiple occasions. So yeah, it's not much of a crowd-pleaser.
7. The Revenant (2015)
Though it will likely go down as the movie where Leonardo DiCaprio gets mauled by a bear, The Revenant, which also stars Tom Hardy in one of his scariest roles ever, is a deeply emotional movie that is part thriller, part western, and all amazing. Leonardo DiCaprio plays frontiersman, Hugh Glass, on the hunt for the man who killed his Native American son. What follows is a harrowing journey into the hellish Dakotas that I still can’t quite shake ever since I saw it in theaters.
6. The Aviator (2004)
“Way of the future. Way of the future. Way of the future.” Leonardo DiCaprio’s role as Howard Hughes might just be his best performance yet, as the rise to success and fall into OCD madness that Leo portrays in this film is the stuff of legend. But this is not a list of Leonardo DiCaprio's best performances. It’s a list of his best movies. That being said, The Aviator is one damn good movie.
5. The Departed (2006)
A film so good that even Mark Wahlberg got nominated for an Oscar, The Departed is the movie that finally got Scorsese his much deserved Best Picture and Best Director win at the Academy Awards. Leonardo DiCaprio plays an undercover cop who infiltrates a crime ring run by Jack Nicholson. I mean, did you read what I just wrote? That sentence right there should be all I need to say about this movie.
4. Shutter Island (2010)
Messing up the protagonist mind also messes tour's too. This movie is directed by Martin Scorsese who is very well known for messing up his audience mind. A Marshall goes to an island to solve the mystery but inturn becomes mystery himself.
3. The Wolf of Wall Street (2013)
The Wolf of Wall Street is the fifth film Leonardo DiCaprio has worked on with Martin Scorsese, and in my opinion, his very best. In it, Leonardo DiCaprio plays Jordan Belfort, a stock broker based off of a real person who made his fortune off of penny stocks. In fact, this is yet another biopic from DiCaprio and Scorsese. But unlike The Aviator where DiCaprio played Howard Hughes and it took place in the 20s-40s, The Wolf of Wall Street took place in the 1980s, so it contained all the sleazy excess that the decade represented. And Leo is just too good as a smarmy Wall Street guy. With that slicked back hair and that charming look in his eyes, it was the part he was born to play. It’s like the Oliver Stone movie, Wall Street, but on steroids.
2. Titanic (1997)
Titanic is so iconic that I don’t even have to look up the date. I will never forget 1997. That was the year that everybody was spreading out their arms and yelling, “I’m the king of the world!” The movie pretty much dominated everybody’s conversation back then, mostly because of its young heartthrob, Leonardo DiCaprio. The fact that Leo went on to become one of the most respected actors in Hollywood after appearing on countless teen dream magazines back then is a testament to how great an actor he truly is.
1. Inception (2010)
Christopher Nolan’s dream caper movie, Inception, is the greatest movie Leonardo DiCaprio has ever been in, bar none. It’s twisty, it’s creative, it’s wonderful, and it’s the kind of action picture that is both incredibly intelligent, but also lands with audiences in all the right ways. Anytime somebody says that they had a dream within a dream, they’ll probably think about Inception.