It was clear early on that there was something special aboutLeonardo DiCaprio. He was nominated for his first Academy Award at the age of 20 forWhat’s Eating Gilbert Grape, and while the fresh-faced actor had already earned “teen heartthrob” status that would only grow when he reached the next level of fame, he was always keen on taking challenging roles rather than going for the flashy male lead. Indeed, films likeThe Basketball DiariesandThis Boy’s Lifearen’t exactly the kind of projects you take when you’re merely seeking superstardom, which is why signing on to star inJames Cameron’s epic romance about the doomed Titanic was a fitting choice for the actor and, ironically, the one that launched him into the “movie star” realm.
DiCaprio’s craft would only blossom further when he madeGangs of New YorkandCatch Me If You Canback-to-back in the early 2000s, working with two of history’s greatest filmmakers and beginning an actor/director collaboration withMartin Scorsesethat would result in the best performances of his career.
And yet, while we can all agree that DiCaprio is one of our finest performers, that little golden statue continues to elude him. With five nominations under his belt, DiCaprio is no stranger to the Oscar ceremony, but each time there seems to be some deciding hook, some other, more alluring narrative that inevitably leads to a DiCaprio loss.
WithThe Revenant, it looks like DiCaprio willfinallybe nabbing that elusive Oscar, and so now feels like as good a time as any to look back on five previous times the long overdue actor was deserving of a statue of his own.
Catch Me If You Can
Steven Spielberg’s breezy con man romp was famously held up whenMartin Scorsese’sGangs of New Yorkshoot stretched on and on, but it’s all the more impressive that DiCaprio was able to switch gears so quickly. Here he convincingly plays Frank Abagnale as a high school teenager, tracing the character’s arc over just a couple of short years and all the while keeping the innocence of youth bubbling just under the surface. It’s an effortless performance that’s in keeping with the film’s light tone, but DiCaprio positively nails the movie’s emotional beats, making Frank’s escapades all the more impactful.
Standout Scene:Frank’s second Christmas Eve call toTom Hanks’ Carl, where he asks him to stop chasing him after having finally found a family withAmy Adams’ Brenda.
Oscar Competition:DiCaprio wasn’t nominated forCatch MeorGangsin 2002, when the Academy instead gave the Best Actor trophy toAdrien BrodyforThe Pianist.
The Aviator
While DiCaprio is solid inGangs of New York, his second collaboration with Scorsese is where he truly soared. A tour de force performance if there ever was one, DiCaprio completely and wholly inhabits the persona of Howard Hughes, imbuing the character with enough empathy to provide a path of understanding for the audience when Hughes’ eccentricities become overwhelming. The sheer challenge in front of DiCaprio, not only in playing Howard Hughes but also in covering such a vast amount of his life, would be enough to dissuade many actors. But DiCaprio seizes the opportunity with gusto and turns in one of his finest performances.
Standout Scene:“The Way of the Future”, obviously.
Oscar Competition:Scoring his first nomination sinceWhat’s Eating Gilbert Grape?, DiCaprio was up against former co-starJohnny Depp(Finding Neverland),Clint Eastwood(Million Dollar Baby),Don Cheadle(Hotel Rwanda), and the year’s winnerJamie Foxx(Ray).
The Departed
Ah yes, the year DiCaprio was nominated for the wrong movie. While Scorsese says he merely madeThe Departedas a commercial play and had no idea it’d finally give him his first Best Director Oscar, DiCaprio’s performance as an undercover agent for the NYPD is deceptively simple.Jack Nicholsonhas the flashy role, but DiCaprio has to toe the line between essentially playing two different people, all the while keeping the character emotionally grounded amidst all the double crossing and whatnot. He does a terrific job of doing so, playing the character just this side of sane all the way up to his shocking exit.
Standout Scene:The interrogation between DiCaprio’s character and Nicholson. You can see the wheels turning inside the character’s head as he considers whether he’s made a giant mistake, and the terror on DiCaprio’s face is very, very real.
Oscar Competition:Well DiCapriowasnominated for Best Actor in 2006, but it was for the forgettableBlood Diamond, notThe Departed. Other nominees includedRyan Gosling(Half Nelson),Peter O’Toole(Venus),Will Smith(The Pursuit of Happyness), and winnerForest Whitaker(The Last King of Scotland).
Django Unchained
DiCaprio andQuentin Tarantinohad been looking to work together for some time, and while it almost happened onInglourious Basterds, Tarantino had a character evenmoredespicable up his sleeve for the performer. DiCaprio’s turn as plantation owner Calvin J. Candie is absolutely revolting, and I mean that as a compliment. This is the one character even Tarantino himself admits that he downright disliked, and DiCaprio brings Candie to life with a mix of delight, aggression, and Southern Charm. It’s quite possibly DiCaprio’s most terrifying performance, as Candie turns from comedic to barbaric on a dime with DiCaprio selling the switch perfectly. You believe this man is capable of both unadulterated glee and despicable horrors, and yet you can’t stop watching him. It’s utterly captivating, and yet oh so frustrating given the fact that DiCaprio wasn’t even nominated.
Standout Scene:The extended dinner sequence, in which DiCaprio literally sliced his hand open when smashing down a glass, but kept going with the scene anyway. That’s the take that ended up in the film.
Oscar Competition:Submitted as a Supporting Performance, DiCaprio was passed over in favor ofChristoph Waltzfrom the film, who eventually took home the prize. Those who also nabbed nominations wereAlan Arkin(Argo),Robert De Niro(Silver Linings Playbook),Philip Seymour Hoffman(The Master), andTommy Lee Jones(Lincoln).
The Wolf of Wall Street
A 3-hour, R-rated dark comedy epic from director Martin Scorsese. Cinephiles were in the bag forThe Wolf of Wall Streetlong before they laid eyes on it, and boy did the finished film deliver. DiCaprio’s powerhouse performance as Wall Street skeeze Jordan Belfort is hypnotic, hilarious, and disturbing—many times all at once. This is DiCaprio at the top of his game, working with Martin Scorsese at the top of his game, delivering a film unlike anything we’ve seen before. If there’s one performance of DiCaprio’s that’s most deserving of the Oscar, this one is it.
Standout Scene:It’s hard to choose, but Belfort’s tet-a-tet withKyle Chandler’s FBI agent on the yacht is pretty spectacular.
Oscar Competition:DiCaprio’s best performance to date also happened to occur against his stiffest competition yet.Chiwetel Ejiofor(12 Years a Slave),Bruce Dern(Nebraska),Christian Bale(American Hustle), and winnerMatthew McConaughey(Dallas Buyers Club) filled out the category as DiCaprio was at least deservedly recognized with a Best Actor nomination.
[Note: This feature was initially published at an earlier date, but in an effort to highlight Collider’s continuing original content, has been bumped to the front page.]
