Leonardo DiCaprio's 10 Best Movies, Ranked According To Letterboxd
Leonardo DiCaprio is one of the most acclaimed actors of this generation, and it's hard to believe that there's only one Academy Award sitting on his shelf. Whether it's an evil slave owner, a survivalist frontiersman, or a has-been actor, DiCaprio only gets better as time goes by.
The actor also works exclusively with directors who can only be called cinematic visionaries. So between filmmakers who have so much freedom and an actor as talented as DiCaprio, together they have made the most entertaining and iconic movies of the 21st century.
10 What's Eating Gilbert Grape (1993) - 3.8
What's Eating Gilbert Grape is what made casting agents sit up and pay attention to the actor. The movie is about the titular character (Johnny Depp), who must take care of his neurodiverse younger brother (DiCaprio).
It was the very first instance of DiCaprio stealing the show. Even at the young age of 19, the actor was the MVP of the movie and gave a better performance than the seasoned Depp at the time. DiCaprio was even nominated for Best Supporting Actor at the 66th Academy Awards, being one of the youngest ever actors to be nominated.
9 The Revenant (2015) - 3.8
It took him years to finally get it, even though many believe DiCaprio deserved an Oscar for earlier roles, but The Revenant was the film that got him his first (and so far, only) Academy Award. But it wasn't a legacy win, which is what it's called when the Academy believes somebody deserves an award based on their entire career, and it's why many believe Martin Scorsese won for The Departed.
DiCaprio truly deserved the win for the 2015 movie. As he played frontiersman Hugh Glass and went through some grueling conditions. According to Vanity Fair, the actor actually crawled into horse carcasses and ate raw bison liver. None of it was faked.
8 Titanic (1997) - 3.8
DiCaprio might not have as many classics under his belt if it wasn't for Titanic. While everybody in the industry believed the movie was going to be one of the biggest box office bombs in history, it did the complete opposite and became the highest-grossing movie of all time — a record it held for 12 years.
But it was almost as if the actor and the movie needed each other. Titanic turned DiCaprio into a star, and being Hollywood's sweetheart at the time, DiCaprio's portrayal of Jack had teenagers paying to see the movie multiple times over. The actor's charm in Titanic is jaw-dropping and his chemistry with Kate Winslet made the fictitious romance in the disaster movie believable.
7 Once Upon A Time In Hollywood (2019) - 3.8
Though it was Brad Pitt who won the Oscar for playing stuntman Cliff Booth, Cliff wouldn't be half as entertaining without Rick Dalton (DiCaprio) and Rick wouldn't be as great with Cliff. Once Upon a Time in Hollywood is about friendship more than anything, and it's a great coming-of-middle-age movie set in the swinging '60s.
Though the DiCaprio-starring and Tarantino-directed Django Unchained is rated much higher on the movie social media platform, Rick Dalton is DiCaprio's best Tarantino-directed role. There are so many flawed nuances to the character and he's essentially the supporting player in his own movie.
6 Shutter Island (2010) - 4.0
Many may have seen the plot twist of Shutter Island coming a mile away, especially if they picked up on all the clues. But regardless of how predictable the final scene was, it's the journey to get there that makes the movie so compelling.
The movie follows U.S. Marshal Edward (DiCaprio) who is sent to a psychiatric hospital to investigate the disappearance of a patient, and he uncovers all sorts of strange goings-on on the island. Of all the collaborations between DiCaprio and Scorsese, this is one of the most interesting because the mystery thriller sits outside both of their wheelhouses.
5 Catch Me If You Can (2002) - 4.0
Just as his breakthrough movie What's Eating Gilbert Grape did nine years earlier, Catch Me If You Can sees DiCaprio acting alongside a more seasoned actor only to completely steal the show.
Even though the 2002 Steven Spielberg-directed flick is one of Tom Hanks' best movies, it's DiCaprio who carries the film, as he plays the real-life genius fraudster, Frank Abagnale Jr. It's one of the most entertaining cat-and-mouse chase movies ever, as Abagnale trots around the world avoiding the FBI, and it comes as close as possible to the comedy of a crime caper without actually being one.
4 The Wolf Of Wall Street (2013) - 4.0
Even though it isn't even 10 years old yet, The Wolf of Wall Street has already reached "classic" status. The movie is quoted all the time and it's endlessly rewatchable, as the three-hour runtime flies by and the credits roll in an instant.
The film expertly satirizes Jordan Belfort's (DiCaprio) lifestyle but also makes it so entertaining that audiences vicariously live through the fraudulent broker, posing an interesting moral dilemma for viewers. DiCaprio perfectly portrays the duality of the character's charming and braggadocious behavior and the struggle of that addictive and pleasure-seeking personality.
3 The Departed (2006) - 4.2
The Departed is the second-best gangster movie of the 2000s according to IMDb, and it's one of the most intriguing Scorsese-directed movies because it's the only one that's set during modern day. But what makes it better than almost any other gangster movie of its decade is the across-the-board, career-best performances.
Jack Nicholson gives a late-career performance that's as good as any of his earlier work, but DiCaprio again proves why Scorsese loves to work with him so much. The actor shows the stress and anxiety that being an undercover cop can have and that it isn't exactly the exciting career that other crime movies make it out to be.
2 Inception (2010) - 4.2
Brooding men is a cliche found in every Christopher Nolan movie, and there's none more brooding than Cobb (DiCaprio), who is doing everything he can to get his wife and children back. But while DiCaprio gives a great performance, the characters are secondary to the narrative and the genius concept of "dream heists."
Inception is another movie that quickly became a classic since its release, and it's the highest-grossing original blockbuster of the 2010s. It poses so many questions, has the most exciting and original action sequences since The Matrix, and has one of the most shocking final shots in a movie ever.
1 Django Unchained (2012) - 4.2
DiCaprio cares about acting so much that if there's a supporting role he thinks is perfect for him, he'll take it. It's not often when actors do that because when they earn lead roles, they aren't willing to step back down.
This is the case with Django Unchained, as Calvin Candie (DiCaprio) doesn't show up until well over an hour into the movie, and he gets killed off pretty shortly after that too. But for the short amount of time he's on-screen, DiCaprio is totally believable as an evil slave owner, and it makes fans crave more villainous roles from the actor. It's a type of character he doesn't play enough.