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The Essentials: Leonardo DiCaprio’s 10 Best Performances

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” (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.

“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” (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.

“Titanic” (1997)
Most people need more than two films to remain forever “certified fresh” as one of cinema’s grandest romantic leads. In 1997, DiCaprio stood at the furthest end of the bow of a little ship screaming, “I’m the king of the world!!” Beyond the silver screen, that roughly translated to: “I’m not most people!!” After stepping out of the shoes of Shakespeare’s eternal star-crossed lover, he took quick reprieve from romance with a dark, supporting turn in “Marvin’s Room,” but when he finally agreed to be a part of James Cameron‘s ambitious epic romance —the most expensive film ever made up until that point— DiCaprio’s career would never be the same again. He portrays Jack Dawson, an impoverished Wisconsin rascal who wins a trip on the ill-fated voyage and, of course, falls in love with Rose DeWitt (Kate Winslet, in one of her essential performances). “Titanic’s” colossal success on every level drowns out all the components that worked together to make up the 2.1 billion dollar sum, but DiCaprio’s and Winslet’s onscreen chemistry combined doe-eyed star-making qualities with unfiltered talent for movie magic. After this film, the teen girl demographic experienced an unprecedented tectonic shift towards full-fledged Leo Mania. The combination of melodrama, romance, and tragedy in the screenplay sparkles through every pore of DiCaprio’s performance, carving the actor’s mainstream appeal in stone and giving him a one-way ticket to superstardom. Today, DiCaprio looks back at the mega event with lots of pride, and underlines how “the movie has really made me be in control of my career.”

“Catch Me If You Can” (2002)
Released a mere five days apart, Martin Scorsese‘s “Gangs of New York” and Steven Spielberg‘s “Catch Me If You Can” were both headlined by DiCaprio in what turned out to be another pivotal year in the actor’s career. It marked the first of five (and counting) films DiCaprio would make with Scorsese, but interestingly enough, it was his performance as real life conman Frank Abagnale Jr. in Spielberg’s film that turned more heads. It’s one of the director’s greatest films of the post-2000s period; combining the forces of comedy, family drama, adventure, and lots of chasing through Jeff Nicholson‘s deft screenplay with incredible economy. This balance of tone and swiftness of pace is reflected in DiCaprio’s central performance as a whip-smart teenager who rebels against his parents’ divorce by high-tailing it away through confidence scams; forging checks, impersonating pilots and doctors, and toying with Tom Hanks‘ FBI agent Carl Hanratty along the way. DiCaprio’s baby-faced features came in handy as the 27-year-old was seamlessly molded into a teenager, but even more crucial was his movie star charm working at maximum capacity for a role that actually required it. He turns suave into sensitive on a dime as Abagnale, making the forbidden fruits of a lavish lifestyle taste way sweeter than anything we’ve seen with the likes of James Bond. And working under the auspices of Spielberg was effective, because DiCaprio acts opposite Christopher Walken, Amy Adams, and Hanks with uncanny candor. This particular role also eerily anticipates his similar —albeit much more unhinged and darkly comic— turn as Jordan Belfort a decade later.

“The Aviator” (2004)
Before Jordan Belfort, though, DiCaprio would portray a drastically different but no less fascinating type of historical persona for Martin Scorsese. For their sophomore collaboration, Scorsese and DiCaprio brought the iconic life of Howard Hughes back onto the big screen and into public consciousness with “The Aviator.” For transporting us back into the Golden Age of Hollywood as if it was filmed in the 1930s, for that heart-stopping plane crash sequence that breathtakingly reminds us it’s a product of the 2000s, and for Cate Blanchett‘s scarily authentic Oscar-winning turn as Katherine Hepburn, the film is a fond memory. But revisiting it now leaves room for one particularly bitter aftertaste; it’s likely the origin point of DiCaprio’s now-infamously contentious relationship with the Academy. How on earth did he not win for this gargantuan performance? Looking back at the eventual Best Actor winner of the 77th Academy Awards, Jamie Foxx for “Ray,” doesn’t make the feeling any less caustic. DiCaprio’s portrayal of the eccentric-billionaire-turned-OCD-hermit was truly the first opportunity for the actor to completely shed his boyish persona and sink his teeth into a complex, multi-layered, larger-than-life biographical figure. He does so with infinite degrees of aplomb and astuteness. Ever the researcher, DiCaprio spent days in conversation with OCD experts and observance of those afflicted with the condition in order get inside the mental process of a germaphobe and hypochondriac. Watch the hand-rinsing scene, the “come in with the milk” and “the way of the future” scenes and tell me he doesn’t absolutely nail it; he powerfully tears your heart out portraying a man whose oversized ego didn’t exactly make him likable. Quite the opposite. 

“The Departed” (2006)
Here’s the Scorsese-DiCaprio crime film that makes “Gangs Of New York” look like a children’s stage-play, with exactly one adult performance (from Daniel Day-Lewis, not DiCaprio, in case that wasn’t clear). Thanks to one of the most successful U.S. adaptations of Hong Kong property (you’re still very much advised to watch “Infernal Affairs“), Scorsese finally brought home the Oscar that had eluded him for decades. “The Departed” is a brilliant showcase of everything that makes Scorsese’s pictures so compelling. Thelma Schoonmaker‘s masterful editing, the last truly monumental performance by Jack Nicholson, William Monahan‘s crackling screenplay; place your finger on virtually any aspect of “The Departed” and you’ll find validation for why it’s one of the best Best Picture winners of this century. DiCaprio’s gritty portrayal of Billy Costigan stands to this reason, namely because “gritty” isn’t something anyone who’s seen any DiCaprio film prior to 2006 would use to describe the actor’s style. As Costigan infiltrates Frank Costello’s (Nicholson) circle of crime deeper and deeper, DiCaprio bears his canines and dances with the devil for the first time in his career. “The Aviator” added an unprecedented air of maturity to DiCaprio’s arsenal, and “The Departed” continued in this vein. It’s even more impressive because he plays a boyish Good Samaritan turning into a volatile force of dark nature right before our eyes. Costigan’s nerve-shot and fragile state of mind resonate all the more precipitously thanks to DiCaprio’s no-holds-barred approach. Ironically enough, the Academy continued its facepalm appreciation of Leo’s towering talents by nominating his showier “Blood Diamond” performance over this one.

“Revolutionary Road” (2008)
Reunited with his “Titanic” co-star Kate Winslet, DiCaprio took suburban domestic turmoil to new levels with his turn as Frank Wheeler in this film. Though it’s Winslet’s passion project, it was DiCaprio’s megastar status that spearheaded the entire production once he committed to the role. With Sam Mendes at the helm and working with Justin Haythe‘s screen adaptation of Richard Yates‘ novel, “Revolutionary Road” is an emotional roller coaster of a film examining the corrosive relationship of a married couple in 1950s Connecticut: two individuals who are crying out for a better life are inextricably trapped and turned into products of their own environment. DiCaprio allows his boyishness to pour into the corporately ambitious Frank in order to personify an empty shell of a man, a cowardly cog of the societal machine who reaches multiple breaking points in his efforts to be the ideal husband, father, provider, neighbor and worker. “I found Frank immediately detestable,” DiCaprio explained to a screening audience, “but then there’s this element to him that you find so entirely sympathetic, because he’s trying to make a happy home.” DiCaprio’s fired-up performance somehow manages to make the line between detestable and sympathetic unbelievably thin in the case of Frank Wheeler. No doubt feeding off of his “Titanic” co-star, DiCaprio consciously removed all traces of romance and melodrama that marked his last on-screen appearance with Winslet to portray someone who is vehemently anti-romantic. The vitriol spewed all over “Revolutionary Road” between the two actors is so rancorous that you find yourself questioning how this man could be the same teen heartthrob from a mere decade ago.

“Django Unchained” (2012)
The prospect of DiCaprio intoning Quentin Tarantino‘s dialogue was made all the more exciting once it was revealed that the actor would appear as a bonafide villain for the first time in his illustrious career. Scorsese’s current muse, the once-upon-a-time baby-faced youth and romantic lead was cast as a detestable plantation owner Calvin Candie, arguably Tarantino’s most vile and unsympathetic villain to date. “Django Unchained” has all the flair of Tarantino’s post-modern stylizations, including Christoph Waltz in the role of the gentlemanly bounty hunter Dr. King Schultz, buckets of blood and vengeful violence, and a soundtrack to die for, but it is most refreshing in its inspired casting choice of DiCaprio. A Southern faux-beau and racist down to the bone, Candie is introduced halfway through the film during the Mandingo fight, one of Tarantino’s hardest-to-watch scenes, and from the second the camera whip-zooms into DiCaprio’s devilish smirk, you’re struck with the realization that this is going to be new territory for him. Candie is a classic love-to-hate villain, his polished facade hiding a simpleminded and morally repugnant weakling, and watching DiCaprio be loquacious, reprehensible and morbidly comic is a level of entertainment we’ve never seen from the actor before, only to be toppled by our next entry in terms of watchable theatrics. In his highlight scene, DiCaprio famously cut his hand on a glass, but was so zoned into character that he just kept going, smearing his own blood all over a slightly grossed-out Kerry Washington. It’s the most famous but by no means only example of the actor’s storied devotion to his craft.

“Wolf Of Wall Street” (2013)
Scorsese’s three-hour examination of Jordan Belfort’s hedonistic lifestyle as a corrupt Wall Street stockbroker was met with a surplus of controversy. The director and DiCaprio, who co-produced “The Wolf of Wall Street” and had been trying to make it since 2007, were met with criticism for glorifying the advantages of Belfort’s millionaire perks and paying too little attention to countless individuals he swindled. The film no doubt treads a fine line between glorification and true representation, but no matter which side of the argument anyone takes, there were a few no-duh points everyone agreed on. Terence Winter’s adaptation of Belfort’s memoir is a sizzling, drug-fueled engine of quotable dialogue and unforgettable scenarios, Jonah Hill and Margot Robbie turned in sensational, revelatory performances as Belfort’s best friend Donnie Azoff and wife Naomi, and DiCaprio tapped into a hitherto unknown source to peel yet another remarkable layer of his craft. The evolution of Belfort as an aspiring Wall Street broker who only jerks off three or four times a week to the Quaalude-popping greed-riddled monster who beats his own wife becomes a master class acting lesson in DiCaprio’s hands. It’s one of the actor’s most physical performances to date (before “The Revenant,” that is), one in which we’re introduced to a whole new array of facial expressions and amped ways of registering intensity. Animalistic, decadent and with pitch-dark comic overtones, DiCaprio’s Jordan Belfort has various shades of Frank Abagnale, Frank Wheeler, Billy Costigan and even Calvin Candie, but is very much a distinct character. For all the controversial debates it spurred, the most blatantly obvious point “The Wolf of Wall Street” made is that in Leonardo DiCaprio, we have one of the greatest actors working today.

There’s very little separating greatness from excellence in DiCaprio’s exemplary oeuvre, which is to say that many of his other roles were considered for this list. He teamed up with another top-class director in Christopher Nolan for “Inception,” but as great as he is in it, he’s no greater than the rest of the rock solid ensemble. In 2008, before they could get ‘Wolf’ off the ground, DiCaprio and Scorsese teamed up for the psychological mind-bender “Shutter Island,” another stellar turn that just fell slightly short of being considered essential. Early turns in “The Basketball Diaries” and “The Beach” got an early start on shredding the actor’s innocent veneer, but neither felt quite right alongside the 10 above. Ditto his Oscar-nominated turn as Danny Archer in “Blood Diamond.” Even when certain films failed to meet critical expectation —as was the case with “J. Edgar,” “The Great Gatsby” and “The Man In The Iron Mask“— DiCaprio’s performances could be singled out as one of the few great things to come out of them.

Everyone’s got a favorite DiCaprio performance —my personal favorite is probably Frank Wheeler, FYI— so now it’s time to hand off the reins to you, dear Playlist readers. Favorite performance? What’s his best in a Scorsese movie? Got objections to my Top 10? You know where to go.

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