Top 10 Leonardo Dicaprio Performances

Meaghan McDonough ’17/ Emertainment Monthly Staff Writer

With this Oscar season being partially dubbed the one where “Leonardo DiCaprio Finally Gets  His Oscar”, it’s time to take a look back at Leonardo DiCaprio’s long (very long), illustrious (very illustrious) career! The Revenant is not Leo’s first Oscar-nominated performance, and it hopefully won’t be his last. Though The Revenant seems to have poised Leo to take home the trophy, is it really the Best Performance of his career? After watching every Leo DiCaprio movie that matters (which, really, is most of them), here is a compiled list of Leonardo Dicaprio’s best performances! Read on to find out what made the cut, where it falls, and whether or not The Revenant is the performance of Leo’s career!

10. Romeo + Juliet

One of the most hotly debated Baz Luhrmann films to date, Romeo + Juliet tells the classic Shakespeare tale but decks it out with mafia empires and a whole bunch of guns and over the top costuming. While it is a word-for-word reimagining of the play–more accurate than most versions of ‘Romeo and Juliet’ ever have been–this film is hot mess in terms of tone, and DiCaprio’s acting suffers for it. It is avant-garde and gaudy, but DiCaprio is plays Romeo so superbly and simply that the two just don’t mix. While DiCaprio’s performance is good enough to carry the film at least part of the way, Luhrmann’s directorial choices taint the whole thing, and drag Leonardo DiCaprio down with it. He also tends to get forgotten about when compared with the larger than life characters, such as Mercutio and Tybalt. If a few side characters can really suppress the actor playing on of the film’s eponymous characters, then what does it say about the actor’s performance? Brutally, it speaks volumes: DiCaprio just can’t hold down the iconic role in a production that so desperately needs him to act up.

9. What’s Eating Gilbert Grape

A drama telling the story of Gilbert Grape (played by a much younger Johnny Depp) who must care for his mentally challenged brother (DiCaprio) and his morbidly obese mother. Sad, and really not much more than that, the biggest problem with this Leonardo DiCaprio performance has nothing to do with his age or the fact he’s a not at all developmentally disabled in real life (political correctness wasn’t a thing in the 90s), but rather with the fact that this film just doesn’t stand the test of time. It’s sad, and that’s all it really is. Leonardo DiCaprio is endearing and heartbreaking, but even that isn’t enough to carry a 90s movie that just doesn’t hold up to 21st century film. Compared alongside other films on this list, this movie is disappointing, as DiCaprio has held the weight of older films on his shoulders since the beginning of his career. Though Leonardo DiCaprio’s performances are usually both timely and timeless, here it does not come through.

8. Gangs of New York

Gangs of New York is the first of the great Scorsese-DiCaprio pairing, but it’s definitely not one of Leonardo DiCaprio’s strongest. A historical fiction film telling the story of the complicated history of 19th century New York as it relates to Irish immigration and the Civil War. DiCaprio’s subdued performance is due in large part to the fact that he’s is competing with Daniel Day-Lewis who carries the brunt of this film–which really is just too much for a film. Leonardo DiCaprio fades into the background, getting lost in the mess.

7. Revolutionary Road

This delicate drama set in the 1950s starring Leonardo DiCaprio and Kate Winslet as a complicated suburban couple trying to come to terms with the lives they’ve fallen into while also raising children. It’s a film built on the existential crises and ennui of 1950s white families, and that’s really where it starts and ends for both DiCaprio and Winslet. They have some sincere and heartbreaking moments, but much of the film is just blank stares as quiet piano music plays in the background. Though it is really beautiful, a true portrait of the struggle of 1950s suburbia, Leonardo DiCaprio doesn’t do a whole lot of work here compared to his other roles. It’s a film in which Leonardo DiCaprio could be easily replaced by any other middle-aged white actor and that’s just not what makes a DiCaprio film enjoyable. Going into the film, one expects Leo to bring something new to the role of disenchanted middle class businessman of the 1950s, but he simply doesn’t. He plays it too safe. The film begins and ends with the depth of DiCaprio and Winslet’s chemistry, but beyond that, nothing worth noting acting-wise.

6. Catch Me If You Can

Catch Me If You Can tells the true story of Frank Abagnale, a young con-artist who successfully manages to earn millions of dollars in cash faking various professions–from PanAm pilot to parish prosecutor–all before his 19th birthday. Abagnale is played by DiCaprio, who performs well as the cunning, cheeky, and captivating character Abagnale is designed to be. Very much a riff on Ferris Bueller’s Day Off–and an enjoyable one at that–the one place this film fails is in convincing the audience that DiCaprio, who is almost thirty in 2002–is supposed to be a high school student. Leonardo DiCaprio matured much more quickly than most actors (or people) do, and it is for that reason Catch Me If You Can fails to convince viewers of Leo’s greatness as well as some of his other films. While he is sickly-sweet charming, cunning and sleazy, it’s not convincing that the thirty-year old actor is just a really charismatic teenager. DiCaprio’s maturity shines through in this role, and not in his favor. While this is usually something that Leonardo DiCaprio pulls off quite well, the role simply called for a more youthful tone that DiCaprio–too far advanced in his life and career, at this point–just couldn’t pull off.

5. The Revenant

Leonardo DiCaprio went through so much to make this movie. He crawled through snow and mud, nearly drowned in a river, had to maintain one of the longest, ugliest beards that Hollywood has ever seen–he deserves an Oscar for the sheer amount of effort he put into making this film. Playing vengeful frontiersman Hugh Glass, DiCaprio maintains control of every scene he’s in, and even some that he’s not in. That being said, his performance is lost, in some aspects, in the sheer weight of the film itself: breathtaking cinematography and incredibly sound editing, in the end, overshadow DiCaprio a little bit. That, combined with the extensive periods of him simply crawling and grunting across screen, make this performance relatively forgettable when compared alongside some of his earlier work.

4. Titanic

A lot of people will question this pick, of course. “But Leo was so young!”, “But the role was so easy!”, “It was so long ago!”. Whether you like Titanic or not there’s no denying the great job Leonardo DiCaprio does in it. This 3.5 hour James Cameron epic telling the star-crossed love story of Jack (Leonardo DiCaprio) and Rose (Kate Winslet) survived one of the most difficult film productions to date and went on to become one of the biggest box office smashes of all time. A big part of that is due to the handsome, talented, charmingly young Leonardo DiCaprio, who stole viewers hearts with his puppy dog eyes, blue collar charm, and sincere declarations of love. His chemistry with co-star Kate Winslet created such a dedication among fans of the film that people are still hoping they’ll get together nearly two decades since the film came out.

3. The Wolf Of Wall Street

The black comedy crime film based on a memoir of the same name was either going to be the biggest hit or the biggest miss of the 2013 Oscar season. While the truth is somewhere in between–some might say mediocre, or mostly good–the real winner in this film is Leonardo DiCaprio. His performance as Jordan Belfort, fraudulent riches-hungry stockbroker,  is extreme in all the right ways: hilarious to frightening, captivating to repulsive, always inevitably expressive. DiCaprio carries a lot of the weight of this movie on his own, only deferring to other actors, particularly Jonah Hill, when he needs some humorous support.

2. The Departed

The ultimate Boston crime-drama, The Departed is one of DiCaprio’s most beloved and fan-protected films, and for all the right reasons. A star-studded spy-versus-spy film with the Irish Mob twisted in, Leonardo DiCaprio plays an undercover state trooper assigned to infiltrating the Irish Mob, headed by Francis “Frank” Costello (Jack Nicholson). Though DiCaprio is competing against Matt Damon and Jack Nicholson, who are both in their prime, and Mark Wahlberg, who is no competition in terms of talent but is (like Damon) a Boston local, DiCaprio manages to stand his ground and then some. DiCaprio shines among the grit and gore, giving a good, old-fashioned performance that you can just watch again and again.

1. The Aviator

Based on a 1993 autobiography, The Aviator depicts the life of aviation pioneer and movie producer Howard Hughes. Crippled by severe obsessive-compulsive disorder, Hughes (Leonardo DiCaprio) struggles to maintain his success and prestige as he grows more and more unstable, experiencing symptoms that even a romance with Katharine Hepburn (Cate Blanchett) can’t save him from. Leonardo DiCaprio is at his absolute best: powerful, charming, serious, and sorrowful–depicting all the complexities of living with mental illness with such natural ease. This, of all the movies on the list, is a movie in which Leonardo DiCaprio really escapes his own ego to become this other person. In portraying a man obsessed with perfection, DiCaprio himself becomes perfect.
Regardless of whether or not you agree with this list, or if you like Leonardo DiCaprio as an actor at all, it can’t be denied that this man has had one of the most noteworthy careers in recent memory. From mental illness to masochistic lover, from developmentally disabled to damaged undercover cop, from poor Jack Dawson to billionaire Jordan Belfort, DiCaprio has played it all and played it (usually) pretty well. Whether or not The Revenant will win him his Oscar, finally, is unknown as of yet; but there’s one thing we can be sure of: he’s earned it. Maybe not for The Revenant, maybe not for any of these movies in particular, but for his career as a whole.