Top 10 Leonardo DiCaprio Performances, Ranked

Over the course of his decades-long career, actor Leonardo DiCaprio has grown from and obviously talented young actor to one of the most recognizable and universally acclaimed actors alive. After so many years as a consistently working actor, it comes as no surprise that Leo has a resume that is nearly a mile long now, and although he has become more selective in the roles that he takes as time has gone on, it’s clear that his pickiness has worked out really well for him in the long run.

DiCaprio has had more iconic and critically renowned roles than most normal actors even dream of achieving across their entire lifetime, and he has built up that legacy all before he has even reached the age of 50. Leo has had a lot of really memorable and impressive performances over the course of his career, but here are his top 10 of all time, ranked.

10 Romeo Montague – Romeo + Juliet

Theoretically it should be pretty difficult to screw up one of the most well known classic characters in all of fiction history, however Leonardo DiCaprio may have had his work cut out for him when it came to portraying Baz Luhrmann’s version of Romeo Montague in Romeo + Juliet.

The skepticism towards this modern version of William Shakespeare’s classic play was understandable, however thankfully the movie more than lived up to it’s own potential and became one of the most memorable movies of the 90’s. And Leo absolutely nails it as the wild and passionate son of the Montague family who risks and loses it all for the girl he loves.

9 Cobb – Inception

Playing the straight man in a huge film isn’t always an easy task, and honestly clearly the premise behind Inception is meant to drive the story far more than it’s own characters do.

But with that said, DiCaprio’s performance in this insane, inventive movie manages to take a lot of huge ideas and ground them in a reality that the audience can actually invest themselves in. As the film goes on, Cobb’s story unfolds in a surprising and tragic way, and it’s hard not to feel for the enormous loss that he bears a lot of personal guilty feelings for.

8 Jack Dawson – Titanic

Titanic has a bit of an unearned negative reputation for being little more than a chick flick with a blockbuster budget, but in retrospect the movie is a lot more than that.

First off, there’s nothing wrong with being a chick flick anyway, but this classic star crossed lover story that ends with Jack’s death and Rose’s realization that she still has her entire life left to live for even though she lost the man she loves deserves a lot more credit than it gets. And obviously the film’s success rests on a lot of things, but Leonardo DiCaprio’s performance as Jack Dawson certainly gave the movie a huge helping hand.

7 Jim Carroll – The Basketball Diaries

After Titanic exploded on to the scene and made Leonardo DiCaprio into the heartthrob of the decade, Leo seemed to put all of his time and energy into redirecting his career into a more “serious actor” direction.

But this clearly wasn’t a new idea that DiCaprio had when he finally had an enormous amount of success to capitalize on, as is demonstrated with his starring roles in movies like The Basketball Diaries. In The Basketball Diaries DiCaprio portrays the fictionalized version of the real life experiences of Jim Carroll, a boy who descended into drug addiction when he was still just a teenager.

6 Hugh Glass – The Revenant

Honestly, the Academy Awards are pretty overrated. And if the very fact that Leonardo DiCaprio won his first and only Oscar for a performance that doesn’t even crack the top five of his best performances doesn’t show that, then pretty much nothing will.

Leo’s performance as Hugh Glass, a man who barely survives a murder attempt and goes off on a journey of revenge, in The Revenant is still a great one and his dedication to the role was very admirable, but it being his most critically rewarded role really only goes to show that awards voters seem to love to watch rich movie stars suffer for the sake of their art more than anything.

5 Calvin Candie – Django Unchained

Most actors don’t revel in the opportunity to play a virulently racist slave owner, but most actors aren’t Leonardo DiCaprio acting in a Quentin Tarantino film. Django Unchained is just the kind of thing everyone has come to know and love Tarantino for, and it’s very rare that any performer turns down an opportunity to appear in one of his films.

But the character of Calvin Candie is undoubtedly one that could have landed like a lead balloon with audiences, so the fact that Leo managed to lean into the role so hard that it has now become one of his most iconic roles is a testament to his abilities as an actor.

4 Arnie Grape – What’s Eating Gilbert Grape?

Within Leonardo DiCaprio’s entire catalog of film work, What’s Eating Gilbert Grape? probably isn’t one of his best films, but it still is one of his best performances. In the film, Leo plays Arnie Grape, the younger brother of the titular character who is developmentally disabled and is supposedly always running on borrowed time.

Honestly this kind of performance could have gone really awry, and even now it’s a bit of a hot button issue to see actors portraying characters with disabilities that they don’t actually have, but luckily Leo doesn’t hit a false note as his performance as Arnie Grape.

3 Billy Costigan – The Departed

Clearly deciding on what actor’s film is the best movie they ever made is entirely subjective, but there is at the very least a pretty strong argument to be made that The Departed may be Leonardo DiCaprio’s best movie of all time (or at least so far).

This movie is an absolute shocking thrill ride from start to finish, and Leo’s performance as Billy Costigan, an undercover cop working for Boston’s scariest crime boss, carries a lot of the movie’s narrative weight. The cast for this Martin Scorsese movie is absolutely start studded too, so the fact that DiCaprio manages to stand out says a lot about his abilities.

2 Jordan Belfort- The Wolf Of Wall Street

Although this movie is based on the real story of Jordan Belfort, a white collar criminal who managed to reach the highest highs and lowest lows on Wall Street, it’s kind of hard to believe that any of this could have ever really happened.

But to Leonardo’s credit, he manages to make one of the scummiest scum bags ever committed to film into a relatively charming, and at least wildly entertaining, character. Leo clearly took a lot of delight in portraying this objectively terrible person, and with the assistance of Scorsese’s direction Jordan Belfort is undoubtedly one of Leo’s best performances of all time.

1 Howard Hughes – The Aviator

Given how prolific and mutually beneficial their collaborations seem to have been, it comes as no surprise that the top three Leonardo DiCaprio performances on this list are all in films that were directed by Martin Scorsese.

But Leo’s best performance of all time (again, at least so far) has probably got to be as the legendary, ultra weird rich man Howard Hughes in The Aviator. Leo had to portray Hughes at a lot of different points in his life, and he absolutely killed it when he portrayed the descent of this notorious ladies man into the unbelievable depths of his own mental illness.