Leonardo DiCaprio has done pretty much everything a modern-day actor could do, genre-wise, aside from anything superhero-related… yet. They might get him one day, like the last human left alive in a Body Snatchers-style film. But otherwise, he’s done blockbusters, more independent films, crime movies, action flicks, and Westerns, among various other genres. Not all of these movies have been slam-dunks, as shown by the likes of J. Edgar and The Beach, but there aren’t too many outright stinkers (give or take a Critters 3). He’s been taking on film roles since the 1990s, and really started pushing himself as an actor by the time the 2000s came around, as Gangs of New York and Catch Me If You Can help demonstrate.
That kicked off the “I need an Oscar” phase of his career, or at least that’s what it looked like from the outside: Leonardo DiCaprio going full throttle in a bunch of high-profile and big roles that kept getting nominated without scoring a win, but that changed thanks to a 2015 release that’ll get mentioned in a bit. What follows is an attempt to highlight the movies of his that can be considered masterpieces, or otherwise feel very close to perfect. These are either the classics he’s been in, or the movies he’s starred in that’ll one day be old enough to be classics. Some say it takes about 25 years for that to happen; for something to be a classic. But we shall see.
6
‘Inception’ (2010)
Directed by Christopher Nolan
Image via Warner Bros.
Best defined as a psychological heist movie, Inception isn’t about stealing something, instead focusing on a mission to implant something. Specifically, the characters here want to plant an idea in a target’s subconscious, which involves infiltrating his mind and battling through various obstacles that exist within. It’s a wild concept for a movie, but Christopher Nolan has a knack for taking ideas that could be disastrous in lesser hands and shaping those ideas into phenomenal – and large-scale – movies. When he “misfires,” he still delivers something that’s engaging, inventive, and kind of admirable (see the divisive Tenet), and when he hits, he hits hard.
There’s also a great ensemble cast here, and a further argument to be made that Nolan is the star of the movie more than any of the (still great) actors he directs.
Inception is one of those Nolan heavy-hitters, standing as one of his best films to date. And DiCaprio is great as the lead character here, taking charge of the whole mind infiltration/heist mission. There’s also a great ensemble cast here, and a further argument to be made that Nolan is the star of the movie more than any of the (still great) actors he directs, but that’s okay. The acting wouldn’t necessarily need to be great for Inception to still deliver as an action/sci-fi film, but thankfully, the acting does happen to be good, and the cast helps push Inception beyond “mere” greatness.
- Release Date
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July 16, 2010
- Runtime
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148 minutes
5
‘Once Upon a Time in Hollywood’ (2019)
Directed by Quentin Tarantino
Image via Sony Pictures Releasing
There isn’t a great deal that happens in Once Upon a Time in Hollywood, but that’s okay, because it thrives as a hang-out movie. And it does explode into something later on, in a way that could be described as a plot twist, at least twisting expectations of what might happen for those who know their Hollywood history. That’s because Once Upon a Time in Hollywood takes place at the tail end of the 1960s and involves quite a few real-world people as its side characters, though the focus is on two fictional people: a washed-up actor who’s struggling to stay relevant (Leonardo DiCaprio), and his loyal stuntman/closest friend (Brad Pitt).
They both navigate a changing industry, overcoming certain challenges, but also, as mentioned before, kind of just hanging out. When Once Upon a Time in Hollywood does take off, the point of it all does reveal itself, but even before then, it’s still a surprisingly fun movie. Pitt and DiCaprio are both fantastic, and the rest of the cast is stacked, too, especially when it comes to actors who were up-and-coming in the late 2010s, but pretty much A-listers come the 2020s. Anyway, good stuff. DiCaprio is also great in another Quentin Tarantino movie, Django Unchained, but that one ends on a bit too much of a whimper to be considered a masterpiece (it’s really strong up until that awkwardly placed second climax).
4
‘The Revenant’ (2015)
Directed by Alejandro González Iñárritu
Image via 20th Century Studios
There is more to The Revenant than it simply being the movie that finally got Leonardo DiCaprio his long-awaited Oscar, but given DiCaprio is the man of the hour (well, of the ranking), you do have to mention it. He went all-out here, and it was about as showy and physical a performance as one could possibly imagine. He plays a man who’s left for dead by the people he ends up wanting revenge against. So, the whole thing is about him surviving in the freezing wilderness while also pursuing those he wants dead, making it both a survival and revenge movie rolled into one.
Well, it’s also a Western, albeit a chillier and more brutal one than the majority out there, and it’s furthermore a film that manages to be exciting during some sequences and then rather contemplative and patiently paced (though never relaxing) during other stretches. The Revenant is undeniably a hectic ride of a film, and a far from easy one to watch, given how raw and gruesome it can get, but DiCaprio’s performance – at least the sheer commitment to it – lives up to the hype. Also, Tom Hardy makes for a pretty great villain, and him being in the cast alongside DiCaprio makes this a bit of an Inception reunion.
- Release Date
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December 25, 2015
- Runtime
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156 minutes
3
‘Titanic’ (1997)
Directed by James Cameron
Before Titanic, Leonardo DiCaprio had starred in some very well-made movies, like What’s Eating Gilbert Grape, The Quick and the Dead, and Romeo + Juliet, but Titanic might well have been the first indisputable classic he appeared in. Actually, some people will dispute the idea of Titanic being a classic, maybe by saying it’s too long, sappy, or predictable. But it is an epic, it is focused on romance, and much of it’s a foregone conclusion, given it’s based on a real-life maritime disaster, so…
If you approach Titanic for what it is, it’s seriously impressive. It’s a blockbuster in every sense of the word, and one of the most impressive epic films of the 1990s. It feels like Titanic was made to appeal to as many people as possible, and though it’s unlikely there are any movies that would appeal to 100% of the population, Titanic does tick an unusually large number of boxes. This film still feels like the disaster movie to which all others might well be compared, and even if it’s broad and crowd-pleasing, it manages to go big and please crowds better than just about any other movie of its size released within the past handful of decades.
- Release Date
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December 19, 1997
- Runtime
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3h 14m
2
‘The Departed’ (2006)
Directed by Martin Scorsese
Image via Warner Bros.
After Gangs of New York, Leonardo DiCaprio seemed to become Martin Scorsese’s go-to lead actor, fulfilling the sort of role Robert De Niro had done a few decades earlier (and both DiCaprio and De Niro would ultimately be cast in Scorsese’s Killers of the Flower Moon). The first outright classic Scorsese film DiCaprio starred in, though, would probably be The Departed, which is a crime/thriller film with a ton of moving parts, owing to the story here pitting an undercover cop and an undercover criminal (the latter being someone who’s infiltrated the police) against each other.
It worked for Infernal Affairs (2002), and it’s reworked well in The Departed, which does branch off a little – and is also more expansive – than the original 2002 movie. It’s a naturally twist-filled flick, and DiCaprio does a great job of being appropriately stressed out for basically the entire movie. Ideally, The Departed will also stress you out, as a viewer, but in a good way. It’s one of the more approachable and exciting (in an in-your-face kind of way) films Scorsese has ever directed, though when it comes to movies he made with DiCaprio, there is one that’s probably even a little better.
- Release Date
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October 6, 2006
- Runtime
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151 minutes
1
‘The Wolf of Wall Street’ (2013)
Directed by Martin Scorsese
The Martin Scorsese movie that’s made the most money, all the while being all about money, is The Wolf of Wall Street, and even if it’s not quite Scorsese’s very best film, it’s probably the highlight of Leonardo DiCaprio’s acting career to date. Lots of that has to do with the fact that DiCaprio has another showy performance he has to give here, and he’s on-screen for so much of what ends up being a very long film. It’s not quite Titanic when it comes to runtime, but it’s also not too far off, being right on 180 minutes in total.
It doesn’t really feel that long, though, given how extravagant, stylish, and fast-paced The Wolf of Wall Street frequently is. DiCaprio plays the real-life Jordan Belfort, and the movie lays out how he managed to amass such a huge fortune through conning various people while working on the titular Wall Street. It’s a funny film, but it’s also a dark, sometimes emotionally intense, and painfully honest one about human nature and what can happen when someone pursues wealth no matter the cost (laying bare how sometimes, there really isn’t much of a cost, even when you’re arrested). It’s not a gangster film, but it looks at a certain kind of crime the way some of Scorsese’s previous movies looked at mob violence, and it ends up being eye-opening and thought-provoking stuff, as a result.
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