Vanity Fair - February 23, 2016


Why Leonardo DiCaprio’s Oscar
History Has Everyone Saying “It’s Time”

by Scott Beggs


It’s not just that he’s never won; DiCaprio’s history of daring roles,
paired with Oscar snubs, makes his near-certain win supremely satisfying.


The Onion recently mocked awards season with the headline “Leonardo DiCaprio Hopes He Screamed and Cried Good Enough in The Revenant to Win Oscar.” It’s a classic Onion joke, taking a truth (in this case about acting) and reducing it to absurdity, but it found a perfect target with DiCaprio—an actor likely to be rewarded with a best-actor Oscar for another great performance, but one almost solely discussed in terms of how difficult it was to film.

Long before he climbed inside a horse carcass or tangled with a bear, the latter-day Brando was using his superstar status to reject the pretty-boy leading-man roles he could have done in his sleep. Instead, he’s picked fascinating and challenging roles that have seen him play everything from a blood-fisted slaver in Django Unchained to an amoral greed machine in The Wolf of Wall Street. Eating raw bison in the freezing cold for The Revenant wasn’t about proving how hard he’d work for an Oscar, but about pushing the limits of what we’d embrace in a movie star on-screen. It’s something he’s been doing since the Oscars first started paying attention to him—and even in looking back at his history of losses and snubs, it reveals the development of a bold career that’s paid off handsomely.

What’s Eating Gilbert Grape

DiCaprio’s first dance with Oscar came before he was old enough to legally drink. He earned a best-supporting-actor nomination for his turn as Johnny Depp’s mentally disabled younger brother in Lasse Hallström’s story of a family trapped in a tiny, hateful Midwest town. Up until that point, DiCaprio was only known as the rebellious son on the failed TV adaptation of Parenthood and as the Hail Mary addition to the slumping final season of Growing Pains, but playing the developmentally stunted Arnie in What’s Eating Gilbert Grape was the kind of role that demanded 100 percent dedication in order to avoid mawkish, insensitive parody. DiCaprio nailed it, scored the film’s only Oscar nomination, but lost to Tommy Lee Jones for The Fugitive.


After opening his career with prestige, DiCaprio chose to dive into slightly more populist fare more suited to his young age—playing a sidekick figure in The Quick and the Dead and a Hawaiian-shirted Romeo for a hypersaturated Baz Luhrmann Shakesperiment. He toyed with awards seasons in Marvin’s Room, playing opposite Meryl Streep and Diane Keaton, but if you believe in snubs, Titanic is the first genuine one for DiCaprio. He watched the romantic disaster epic get 14 Oscar nominations (including two acting nominations for Kate Winslet and Gloria Stuart) without him. For what it’s worth, Winslet and Stuart were left off the dais, too, while the best-picture winner picked up the lion’s share of technical and craftsmanship awards. Even if he’d been nominated for anchoring the film with his free-spirited character (and noble sacrifice at the end), he’d have assuredly lost to that year’s winner: Jack Nicholson for As Good as It Gets. His consolation prize? Being King of the World, of course.

The Man in the Iron Mask

Largely, sensibly forgotten today, The Man in the Iron Mask is the kind of movie where you can see everyone involved gunning for prestige without ever hitting the mark. It was a historical epic at a popular time for the genre; it was the directorial debut of Randall Wallace, the Oscar-nominated screenwriter of Braveheart; the cast was swimming with talent, and DiCaprio was front and center in a dual role as the despotic King Louis XIV and as the noble hero of the story. As a harsh reminder of Hollywood math, all of these big numbers added up to zero.

Catch Me if You Can and Gangs of New York

DiCaprio’s modern prestige era begins in earnest when he plays a young con artist who leads Tom Hanks on a merry, counterfeiting chase around the globe. As Frank Abagnale Jr., he was forced to run through a large range of situations and emotions while staying realistic as a frightened kid who needed stability more than flights of fancy. It’s a delightful Spielberg adventure, and while it scored a best-supporting-actor nomination for Christopher Walken, it was largely overshadowed by DiCaprio’s other movie that year, which opened five days earlier.

Gangs of New York was the first collaboration between DiCaprio and Scorsese, and, just like Titanic, DiCaprio watched its 10 nominations sail by with empty hands. At this point, it’s O.K. to wonder if there’s a conspiracy afoot—especially for Scorsese, who hadn’t won an Oscar at that point in his exemplary career and who lost that year to Roman Polanski for The Pianist. Gangs of New York has the distinction of having the third-highest amount of Oscar nominations without a single win, but it was also just the beginning of a barn-burning series of Scorsese/DiCaprio films.

The Aviator

Another entry on the list where everyone involved seemed primed for Oscar glory, DiCaprio plays the emotionally ridiculous Howard Hughes as he devolves from wealthy success to pee-collecting shut-in. Powerfully ambitious, The Aviator (and two other biopics, Ray and Finding Neverland) was somehow overshadowed by Clint Eastwood and Million Dollar Baby. The silver lining was that, after helping other movies to massive piles of nominations, DiCaprio finally got one of his own. It was his first since What’s Eating Gilbert Grape in 1993, but he lost to a phenomenal Jamie Foxx in Ray.

The Departed and Blood Diamond

Unfortunately for DiCaprio, his third collaboration with Scorsese would see a return to the old pattern of propelling a movie to Oscar success without tasting any of his own. The Departed got five nominations and won best picture, but DiCaprio wasn’t included; instead he received a best actor nomination for Blood Diamond, one of five for that film, for his role as a Rhodesian gunrunner who grows a conscience in the latter days of Sierra Leone’s civil war. Blood Diamond was appreciated for its intensity and real-world gravitas, but it was one of the weaker contenders at the Oscars that year. In a year dominated by biopic nominees, DiCaprio ultimately lost to Forest Whitaker in his searing turn as Idi Amin in The Last King of Scotland.

J. Edgar

After the minor Oscar success of Revolutionary Road—which saw DiCaprio and Kate Winslet re-united, but with no nominations for either of them—and big-think genre work like Shutter Island and Inception, DiCaprio returned to Oscar’s wheelhouse by teaming with Clint Eastwood and Oscar-winning screenwriter Dustin Lance Black for J. Edgar. Playing Hoover, the real-life bad guy protagonist in a sweeping story of the titular F.B.I. chief’s miniature descent into paranoia, DiCaprio committed himself fiercely—but the tepid drama was shut out of the Oscar conversation completely.

Django Unchained

Here’s where it gets interesting. The following year, DiCaprio appeared as an insane slave owner with a million-dollar smile for Quentin Tarantino’s revenge “southern,” a surprising casting choice given all the cruelties and N-bombs the provocative auteur would likely toss DiCaprio’s way. The conversation was fueled further by Will Smith’s rejection of the title role, ostensibly to keep his bankable nice-guy image intact. Was DiCaprio’s first role as a villain a sign that he was even more anxious to win the Big One? Hardly; he seemed to have stopped worrying about it, choosing instead to go for broke in increasingly more ambitious roles and let the chips fall where they may. He was working with a re-emergent filmmaker hot off of Inglourious Basterds, which scored an Oscar for its villain, but Calvin Candie is a far more viscerally abhorrent figure than Christoph Waltz’s charismatic Nazi. The tale of DiCaprio cutting his hand open and proceeding to rub it on Kerry Washington’s face is the stuff of method-acting legend, but it was also destined to be overlooked come nominating time—Oscars love villains sometimes, but even charismatic bad guys can go too far.

The Great Gatsby and The Wolf of Wall Street

Once again tackling two massive roles in a single year, DiCaprio returned to Luhrmann’s world of literature-bending design and melodrama and Scorsese’s realm of bombastic hedonism and profanity. One movie saw him throwing Easter-candy-colored shirts off a posh dressing room balcony while the other saw him crawling like a glitching, six-foot baby robot to his Lamborghini. You already know which one earned him a nomination. (“The Lemmons!”) One was a classically dramatic turn with a creative twist, while the other was an insane roller coaster with real-world implications designed by Scorsese—and neither were remotely like the stereotypical “Oscar bait” as we know it. This was DiCaprio simply swinging for the fences, with the kind of dedication he showed way back when with Gilbert Grape. The better, bolder performance—as DiCaprio may very well have expected—proved too much for the Academy to handle. He lost to Matthew McConaughey for Dallas Buyers Club.

The Revenant

Which leads us to this latest Oscar season and the latest and best chance for DiCaprio to go home with a naked statuette. His turn as a frontiersman left for dead and beat up by a grizzly bear is another all-in performance for an actor who seems to collect once-in-a-lifetime experiences even more than he does trophies. The Revenant is also a technical marvel from an Oscar-winning director that dominates the field with 12 nominations. While many other categories are toss-ups for Oscar prognosticators, DiCaprio’s win for best actor—after 22 years of stellar work and so many near-misses—is the only thing anyone can agree on. The only downside is that the marketing push for The Revenant’s award season has focused more on how difficult the movie was to make (it was cold! He fought a bear! He slept in animal carcasses! He ate a gross part of a bison!) instead of the damned perfection DiCaprio displays in battling the wilderness and the crueler angels of man’s nature.

As with his mouth-foaming spasms in The Wolf of Wall Street, breaking open a vein in Django and the whole-hearted embodiment of his first Oscar-nominated role in Gilbert Grape, DiCaprio had to dive deep into another person’s life and only come up for air once Alejandro González Iñárritu called it a wrap. DiCaprio put himself through hell, yes, and we’ve heard all about it, but it’s the performance he brought back through the flames that demands recognition. It’s a shame that the conversation has been so dominated by the belief in DiCaprio’s desire to chase an Oscar because it’s more the case that Oscar is just now catching up with him.