Leonardo DiCaprio's Top 10 Roles, Ranked

This Sunday, Award Show Season closes with the most prestigious one of them all, the Oscars. Besides looking forward to watching Chris Rock make white people feel uncomfortable, this Oscars is especially notable for one thing: Vegas has most the famous actor of his generation, Leonardo DiCaprio, a massive -5000 favorite to nab his first Academy Award for his performance in The Revenant. We’re all big Leo guys at Barstool (who isn’t?) so in honor of his coronation, I put together my DEFINITIVE RANKING HOT TAKE list of the ten best performances of his career. Five disclaimers before we get going:


DISCLAIMER ONE: This list could be in almost any order. There are better actors than Leo, but no one better at picking scripts. Every movie on this list is a goddamn powerhouse. Trust me, I went back and forth on all of these.


DISCLAIMER TWO: No Gangs of New York. Dope movie. One of the best 4 movies he was ever in. But he has to be penalized for getting absolutely blown off the screen by Daniel Day (as is almost everyone who goes toe-to-toe with Sir Daniel) and some cringeworthy moments with the accent. One of his ten best movies, not one of his ten best performances.


DISCLAIMER THREE: I snubbed Inception. Again, not totally his fault. But Inception was awesome because of plot, not character, and Dom Cobb was pretty vanilla ice cream. Leo did a great job of keeping the story going, but if you can’t come up with three adjectives to describe a character, it isn’t among an all-time great’s all-time best.


DISCLAIMER FOUR: Didn’t include Titanic, but don’t let anyone tell you that means I don’t love a good romance story. Because I do.


DISCLAIMER FIVE: Some spoilers in that I talk about specific scenes, but I won’t give away any endings. Besides, you should have seen all of these any way.


Now onto the list.


10- Jay Gatsby, The Great Gatsby


It’s hard to play an iconic character that everyone who did the assigned reading in high school is familiar with. Gatsby has to be the ultimate charmer: a handsome, mysterious ladies man with an enormous fortune, but also equally enormous obsession. Leo had to tackle an icon, nailed it, and was easily the best part of the movie.


9- Jim Carroll, The Basketball Diaries


A lesser-known role because it’s a lesser-known movie, but very, very, very good. The depravity and complete abandonment of dignity that comes with drug addiction is something a lot of actors don’t have the humility to portray in all its filth. Leo does though. Show the scene of Leo’s shameful and desperate face when he lets a guy on a train go down on him for a couple bucks to buy crack in every public school, and I guarantee it’ll have a lot more kids Just Saying No than Nancy Reagan ever did.


8- Calvin Candie, Django Unchained


Probably his most controversial role, criticism-wise. Some thought he was brilliant and deserved the Best Supporting Role nod. Others found him to be an awkward puzzle pieces that didn’t quite fit into the rest of the movie. I’m in-between. I think he was fine, but also don’t think the cool, understated style Leo best thrives in fits perfectly with the vibrant, fanzine world of Quentin Tarantino. Fun fact you have seen 149 times if you go on the Internet: The blood smearing scene is real blood. Leo cut his hand during the scene and just went with it. That’s why everyone looks so disgusted. Actors are weird, man.



7- Frank Abagnale Jr. , Catch Me If You Can


Frank Abagnale is a unique role in the sense that the character is an actor himself. Leo at the age of 28 was able to portray the boyish charm that Frank used to hoodwink and enter the most exclusive echelons of American society, but still be able to show flashes every so often that beneath it all, he was just a scared kid on the run. The fact he could convincingly be a high schooler and then Amsterdam Vallon in Gangs of New York the same year also proves that he is a vampire who can change his age at will.


6- Teddy Daniels, Shutter Island


It’s hard to write about this movie without giving away the ONE HUGE SPOILER and I don’t want to ruin it for people, so all I’ll say is in a movie that makes you say WTF he is able to be as shocked as the audience is and leave enough of an open-ended question in the final scene to give anyone who has seen it a spirited debate about what actually happened.


5- Danny Archer, Blood Diamond


I love this movie and am shocked by how many people think it has aged poorly. First off, the South African accent is one of the hardest to pull off and DiCaprio was able to get it almost perfectly (one of my buddies I grew up with is South African so I think I’m qualified to weigh in on that.) Secondly, I think a lot of people were waiting for some moment of total moral redemption where Danny disavows his entire livelihood after doing the one good thing he has ever done for Solomon. But that’s not the point of his character. Danny Archer isn’t a terrible person, but someone who has been shaped and molded by his experiences and environment. He isn’t ashamed of what he does, because what he does is an integral part of who he is. That doesn’t make him a monster, just a product of his environment, and it’s easier for him to just live in that fucked up ecosystem than it is for him to reflect on that fact. I thought that came of really well in his performance, so I’m putting it up high.



4- Hugh Glass, The Revenant



It’s a shame that this is the role that will get Leo his hardware when it’s on the fringe of his Top 5 of all-time. But to his credit, I have never seen grunting the way he grunted in that movie. That was some A+ grunting. He also excelled in the areas of crawling and looking outwards in desperation.


3- Howard Huges, The Aviator



I like this scene a lot because Leo has to pretend like there is an actress who doesn’t want to have sex with him any more which must have been really hard for him.


2- Billy Costigan, The Departed


I admit I’m biased here, because The Departed is maybe my favorite movie of all-time. But COME ON, who could ever forget the scene of Leo in the therapist’s office, giving an emotionally-wrenching monologue on being unhinged to the point of suicide, all the while keeping up the posture of a Boston tough guy AND maintaining his position as the smartest guy in the room. DiCaprio was able to portray a sustained nervous breakdown throughout a two-hour movie, brought sensitivity and vulnerability to the Irish street kid persona, and had a Boston accent that wouldn’t be totally ridiculed by everyone from Massachusetts. And for that, you’re going to give him two pills? Two pills? Why not just give him a bottle of scotch and a handgun to blow his fucking head off.


1- Jordan Belfort, The Wolf of Wall Street


The role that launched a thousand douchebags. In my opinion the greatest Leo role ever, but one that gets underrated and mocked because of how many kids in croakies at Patriot League schools unironically embraced the Belfort character. But just reducing that performance to “Leo was really good at being an asshole” overlooks the entire point of the movie. Wolf of Wall Street began with a Jordan Belfort narration for a reason; it was him selling to us, the audience, the lifestyle he led. The movie is his justification of the things he had done. We are supposed to be seduced by it, but also be disgusted by it. You fucking HATE Jordan Belfort, know exactly what type of dickhead he is, but part of you kinda has to think “Damn I wish I could’ve done that.” Belfort has to be charismatic and revolting at the same time, something Leo pulls off despite the insanely high difficult in doing so. And also, the entire Lemon Quaaludes sequence? As good as physical comedic acting gets these days.


Tell me to kill myself because you don’t agree with this arbitrary list made for entertainment purposes on Twitter @CharlieWisco