Leonardo DiCaprio is one of the most sought after and talented actors working in Hollywood today. But there’s no denying it. He also really knows how to pick great movies to star in. And while there are a whole slew of great movies he decided not to star in, almost every movie he has chosen to be in has ended up being one of the best movies of that respective year.
In fact, there are so many great Leonardo DiCaprio movies that it was tough to narrow it down to just ten (Sorry, Catch Me If You Can! Sorry, Blood Diamond!). And with his recent Best Actor Nomination for Once Upon A Time... In Hollywood, it looks like the roles will keep on coming his way at a steady clip. So here are the top ten best Leonardo DiCaprio movies ever made. And oh yeah, sorry, Shutter Island! Man, this is going to be a tough list to make. Spoilers up ahead, of course.
10. What’s Eating Gilbert Grape (1993)
Johnny Depp may have been the star of this 1993 drama, but Leonardo DiCaprio, playing a mentally disabled boy named Arnie, stole the show. It was also Leo’s very first Oscar nomination, which was well warranted. The film, in a nutshell, is about a young man, played by Johnny Depp, who must become the head of the household after his father commits suicide, and his mother’s crippling depression causes her to gain massive amounts of weight. But again, the film is really bellied by Leonardo DiCaprio’s stellar performance, which is exceptional.
9. 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.
But for a movie about a failing marriage in the 1950s, it feels disturbingly modern. This might be because it tackles heavy themes such as infidelity and existential anxiety. Michael Shannon also makes an appearance as a man who was once in an insane asylum and speaks his mind in the worst possible situations. It may not be Leo’s best performance overall since he sometimes goes a little overboard with the shouting, but as a film overall, it’s a powerhouse. One of director, Sam Mendes’s, best.
8. 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.
The story concerns a slave, played by Jamie Foxx, who gets trained by a bounty hunter, played by Cristoph Waltz. The two of them successfully gun down three outlaws, and then go on a mission to save Django’s wife. But at the center of the story is Leonardo DiCaprio’s plantation owner, Calvin J. Candie, who got so into his role that he even cut his hand for real and just kept on acting. Now that’s commitment. Django may be B-level Tarantino for me, but B-level Tarantino is pretty much A-level everybody else, so it definitely fits on this list as one of the greatest movies Leonardo DiCaprio has ever been in.
7. 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.
It’s all in the storytelling. Martin Scorsese’s biographical film about Howard Hughes moves at such a brisk pace that you're probably not even aware that you’re learning about one of America’s most fascinating individuals. From Hughes directing Hells’ Angels, to his dating of Audrey Hepburn (amazingly played by Cate Blanchett) to Hughes’s deterioration into madness, The Aviator is one for the ages.
6. 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.
It should be noted that this is the role that Leonardo DiCaprio won his first Best Actor Oscar for. And while the story may differ from actual history, the movie is both beautiful and disturbing enough for me to let all that go and just “enjoy” everything else that takes place on screen. If I can even use the word “enjoy” to describe my experience. And that last confrontation between Leo and Tom Hardy where DiCaprio uses Dohmnall Gleeson’s corpse as a decoy… well, it doesn’t get much better than that.
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.
But there’s more, of course. The Departed features an all-star cast, with Matt Damon playing a hood posing as a cop. What follows is a nail-biting movie that has one of the most startling and abrupt death scenes in movie history. This is one film where you really don’t know where it’s heading until the bittersweet end.
4. 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.
You know the story. A poor man meets a rich woman on the fated boat that crashed into an iceberg, and the poor man freezes to death while holding onto a floating door. Cue the tears. Also in the movie is Billy Zane looking cool shooting a gun, and Kathy Bates being saucy. Titanic had young women around the world wanting Jack to paint them like one of his French girls, and it still surprisingly holds up today. A great, great movie that has stood the test of time.
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.
Matthew McConaughey makes an appearance, pounding his chest and humming some ridiculous song, Jonah Hill delivers possibly his best performance of his career as Belfort’s sleazy business partner, and Margot Robbie plays his impossibly beautiful trophy wife. It’s definitely one of Leo’s funniest movies, and at the time, it even held the record for the most f-bombs in a single movie. Now that’s saying something!
2. Once Upon A Time… In Hollywood (2019)
Once Upon A Time…In Hollywood is both peak Tarantino and peak Leonardo DiCaprio (Oh, and peak Brad Pitt, too!). So you know it had to land high on this list. DiCaprio plays Rick Dalton, a former TV western star who tries to branch off into movies but finds that he's not so successful. This leads to scenes of Dalton freaking out on auditions, including one specific scene where he has a fit of rage in his trailer after messing up his lines. And would you believe that that scene was totally improvised?
Nestled within Once Upon A Time, though, is a snapshot of a bygone era of Hollywood that is all the more impressive because of its attention to detail. Sure, much like Django Unchained and Inglorious Basterds, this is yet another of Tarantino’s revisionist history lessons. But the whole film is so impressively done and funny, that it all comes together and makes for one of the most enjoyable Leonardo DiCaprio movies to date. This one will age well. I can feel it.
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.
Everything is great about this movie—the cast (Tom Hardy again! Michael Caine!), the concept, the ending. Oh, man. That ending. Even Leo doesn’t know what to make of that ending. Inception is pretty much the perfect movie, and Leonardo DiCaprio is the star of it. What more needs to be said?
So while Mr. DiCaprio has starred in a long list of masterpieces, it looks like he won’t be hurting for work anytime soon. Here’s to another 30 years of Leonardo DiCaprio!
Rich is a Jersey boy, through and through. He graduated from Rutgers University (Go, R.U.!), and thinks the Garden State is the best state in the country. That said, he’ll take Chicago Deep Dish pizza over a New York slice any day of the week. Don’t hate. When he’s not watching his two kids, he’s usually working on a novel, watching vintage movies, or reading some obscure book.
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