The Essentials: Leonardo DiCaprio's 10 Best Performances

We’re heading straight into the belly of the beast, so everyone hold on to your hats. Awards season is about to go full-swing, and of the films still left to be released in December, Alejandro González Iñárritu‘s “The Revenant” is dominating a lot of conversations. Set for a limited release on Christmas Day, the film already screened for critics in L.A. and New York, and while early word appears to be mixed on the film itself, unanimous murmurs seem to indicate that this could be Leonardo DiCaprio‘s time. Recent reports have emphasized the incredibly tough conditions of the shoot, and DiCaprio himself stated that it’s the most difficult film he’s even done, but whether all of that is going to earn the actor his first Oscar is yet to be seen. Any early proclamations of him being a front-runner should still be taken with a grain of salt the size of Titanic’s iceberg. In any case, all this talk gives us the perfect opportunity to remember just how superficial it is to measure Leonardo DiCaprio’s roles against how many times he didn’t win, or should’ve won, the big prize.

As much it might be fun to joke about DiCaprio’s tumultuous relationship with the Academy of Motion Picture Arts & Sciences, what can get sidelined is the man’s powerhouse acting. It’s a fascinating exercise to trace his rise to fame from remarkably talented child actor and mega-popular teen heartthrob to the fully formed, infamously dedicated actor we know today. He’s got a filmography that started out in the early ’90s but boasts less than 40 feature films, which is as indicative of his off-the-set commitments in areas of climate change as it is of his influence in Hollywood. He’s one of the few actors with the privilege of handpicking his roles, and once something gears into production, his word holds near-equal weight to the director’s. So It’s a good that he’s legitimately one of the greatest actors working today (phew!).

READ MORE: The Essentials: 16 Great Robert De Niro Performances

In order to celebrate an invaluable player in this game we love so much while most of us still breathlessly await “The Revenant,” I’ve run down the actor’s 10 essential performances. There’s a kind of double-edged duty to this article; on one hand, it lists 10 reasons why Leonardo DiCaprio should’ve already been an Oscar winner, while on the other it serves as a reminder that whether or not an actor has won an Oscar is often a skewed barometer for measuring excellence in the film industry.

So, without further ado, let’s dive in!THIS BOY'S LIFE, Leonardo Di Caprio, Robert De Niro, 1993, in Boy Scout uniforms
“This Boy’s Life” (1993)
“Doing ‘Boy’s Life’ is such a step up in my career. Such a difference, I mean, it’s real acting as opposed to just being cute or whatever. You know what I mean, right?” answered the 19-year-old DiCaprio to film critic, Mark Greczmiel. The transition from “being cute or whatever” to “real acting” is in a league of its own when it comes to certain performers, and the year 1993 found DiCaprio as the likely leader of this league via two adaptations. The first was Tobias Wolff‘s memoir “This Boy’s Life,” starring Ellen Barkin as single mother Caroline and DiCaprio as her son Toby. The pair moves to Seattle in search of a peaceful domestic life and are presented with an idyllic facade as such in the form of Dwight Hansen (Robert De Niro). But Dwight’s house rules leave both Caroline and Toby psychologically harassed and physically abused, until the day Toby decides enough is enough. It’s harrowing, made all the more emotionally wrought and mentally draining by the two pivotal forces of good and evil as personified in the DiCaprio and De Niro characters. If you’re a 19-year-old kid whose most famous credit before doing this movie is “Growing Pains,” and you’re pulling your own weight against Robert friggin’ De Niro? The future shines bright, indeed. Breathing life into a fully three-dimensional character and already showcasing an embarrassing amount of range, DiCaprio’s Toby Wolff is slightly overshadowed by the next entry, but let’s not get it twisted as to which of the two was the genuine breakthrough.Wbat's Eating Gilbert Grape Leonardo DiCaprio
“What’s Eating Gilbert Grape” (1993)
“This Boy’s Life” came out in April of 1993, but as far as transitioning from adorable bubble-gum ad kid to the super serious actor possessing white-hot intensity, DiCaprio’s performance in “What’s Eating Gilbert Grape” is pivotal. It made something abundantly clear to the world from there on out: this kid can do drama. Adapted by Peter Hedges from his own novel, the film follows the travails of the dysfunctional Grape family in Iowa; brothers Gilbert (Johnny Depp) and Arnie (DiCaprio), their two sisters Amy (Laura Harrington) and Ellen (Mary Kate Schellhardt), and their morbidly obese mother Bonnie (Darlene Cates). Gilbert’s relationship with his younger brother Arnie, who is mentally handicapped since birth and thus in need of extra protection and care, is the stirring epicenter of the film —which, let’s be honest, is something of a forgettable piece of Oscar bait. The film’s lasting legacy has become DiCaprio’s revelatory turn as Arnie Grape; fiercely delicate and tough to stomach purely based on utterly convincing realism, it’s the earliest DiCaprio performance where we see the actor’s innate knack for controlled spontaneity; it’s a bewitching trait ingrained into his acting style that keeps audiences constantly fixated on his presence on screen, eagerly anticipating what he’ll do next and how he’ll do it. It was his first of many Oscar nominations, though that’s emphatically besides the point of the magnificent performance itself.Romeo + Juliet Leonardo DiCaprio
“Romeo + Juliet” (1996)
For those of us who grew up in the ’90s, the mania over Leo —the prodigiously handsome romantic lead who can act and then some— was palpable. Trust in his acting talents was cinched even tighter with 1995’s dark drug-addiction story “The Basketball Diaries,” but it was in Baz Luhrmann‘s modernized adaptation of William Shakespeare‘s timeless tragic romance that DiCaprio became the bane of every boyfriend’s existence. Shame on both you and your high school teacher if you need a narrative refresher for “Romeo + Juliet,” as it’s literally the most famous boy-meets-girl story ever told. But… OK, here goes: When Romeo (DiCaprio) meets Juliet (Claire Danes), their connection is life-altering, but since they come from rival families, they aren’t allowed to be together. That’s the nutshell for what is one of the Bard’s most popular and most quotable tragedies, and what Luhrmann does with the post-modernization (Verona becomes Verona Beach, swords are guns, the Montague’s and the Capulet’s are rival mafia families…) injects a contemporary zest that works pretty damn effectively. DiCaprio won the Silver Bear at that year’s Berlinale for his efforts as Romeo, and when you re-watch how his tragic hero gets incised with passion, drunk on love, and tempered by violence, its clear this is role he was born to play. It was the perfect opportunity for DiCaprio to flex his range and hone in his flair for the dramatic through tragedy, romance, and wails of exasperation at a fate so cruel.