Choosing the best Leonardo DiCaprio movies is a pretty tall task. Having worked with pretty much every great director in the business and finally won an Oscar for Best Actor, DiCaprio is on a lot of people’s short lists as one of the most talented actors in Hollywood. So, naturally, he’s given us a lot of great roles to digest. But we’re going to give it a shot and put forth a top-five.
5. Inception
Let’s just say right off the bat that narrowing DiCaprio’s greatest hits down to just five is an absurdly difficult task. Rolling Stone, which tends to be particularly effective in lining up pop culture countdowns and retrospectives, delved into Leo’s best work and put 27 films on their list. Incidentally, that list also had Inception at number two overall, and with good reason. For pure entertainment value and impact, it’s right up there with the top contenders.
I actually think Inception is probably the most entertaining movie on this list. It’s the one I’m likeliest to re-watch on a dull weekend night, and the one I’d be most incredulous to learn that a friend hasn’t seen. Christopher Nolan is a genius, and Inception is one of his many masterpieces. Leo carries the project in extraordinarily convincing fashion, and I’ve only kept it at number five (as if that’s a bad thing) because I believe the following roles were more demanding.
4. The Great Gatsby
I imagine this will be somewhat surprising to some readers, but as a self-proclaimed book nerd I actually found a lot to appreciate in Baz Luhrmann’s over-the-top recreation of F. Scott Fitzgerald’s Gatsby. Here’s the thing about this character that everyone seems to misinterpret: he’s not just rich, he’s insanely wealthy, and he acts like it. To back up that point, Lottoland, an online lottery platform that occasionally does fun things like discussing lottery predictions or writing about what jackpot wealth can buy, presented a list of fiction’s wealthiest characters. And Gatsby made the cut, worth an estimated $9 million in the 1920s (that’s around $112 million today).
If you want to tell me Robert Redford captured the persona of a guy worth that kind of money in his own interpretation, we don’t have much to talk about. Leo, on the other hand, was a proper caricature of a wealthy playboy with a hollow (or rather, deeply wounded) soul underneath all the glitz and glamor. It was a fun, if not intoxicating, performance that was more accurate than a lot of people gave it credit for.
3. The Departed
Too often, The Departed is branded as some kind of modern mob movie. And yes, technically that’s more or less what it is. But when you hear the term “mob movie” you tend to think of Italian-American New Yorkers wearing dark suits, discussing “family” matters in smoke-filled rooms and Italian restaurants, wielding Tommy Guns, rigging casinos and the like. A lot of movies that fit that description are terrific, but they’re also pretty formulaic and in some cases just about interchangeable.
The Departed, on the other hand, is a unique take on organized crime in Boston and therefore had the capacity to surprise. By pretty much any account you can find it was well written and wonderfully acted, and Leo’s performance stood out above the rest. As an undercover FBI agent cozying up to Jack Nicholson’s terrifying crime boss Frank Costello, DiCaprio gave one of his deepest and most effective performances. This one is also right up there with Inception in terms of re-watchability.
2. The Revenant
As you probably noticed if you tuned in to Hollywood news at all in the last year, The Revenant won a lot of awards—including, finally, that elusive Best Actor prize for Leo. Viewed by many as one of the most frequently and wrongfully snubbed actors where this award was concerned, DiCaprio finally broke through, and because of that, The Revenant will always be recognized as one of his best movies.
I get that some people found this movie to be a little bit tedious, lacking a plot, or “bold, beautiful, and dumb.” I also get that some people thought it was a shameless or desperate Oscar reach by Leo. But you know what? That doesn’t make it any less incredible. The Revenant is a gorgeous film that was about as demanding of its cast as a movie could possibly be. And with very few lines of dialogue, Leo pulled a Tom Hanks-in-Castaway and brilliantly depicted the emotional journey of a man struggling for survival against astronomical odds.
1. Blood Diamond
The fact that the previously referenced Rolling Stone article ranked Blood Diamond as Leo’s 19th best film is one of the great crimes of the 21st century. Here, too, I understand that there are some criticisms. Some felt the movie tried a little too hard to make a statement. Some people felt that it wasn’t accurate enough in making that statement. And others had gripes with Leo’s accent.
I happen to disagree with those criticisms. This is a massive and supremely impactful film that ought to cause anyone with a heart to think twice before blindly purchasing a diamond. It did make a profound statement without sacrificing any entertainment value, and it accurately depicted some of the true horrors of rogue warlords and child soldiers. More importantly, however, Leo was simply fantastic as Danny Archer, a cynical smuggler who shows his better side when life gives him a reason to in one of the actor’s best roles.
Josh Farris is a freelance writer out of Apex, NC. Josh has followed Leo’s career since seeing his role in The Basketball Diaries and wasted endless amounts of time pondering how the Best Actor Oscar eluded him for so long.
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