Leonardo DiCaprio had that hard thing to do. You know, that thing where you’re the most famous young actor in the world, but want to be taken seriously. That thing where just one wrong role could ruin your career. Thankfully, DiCaprio has consistently made excellent character choices, bringing to life one fearless and commanding man after another. While he’s currently killing it in The Wolf of Wall Street, I thought it’d be fun to look back at some of the best work he’s done yet.
5. The Basketball Diaries (1995)
as Jim Carroll
DiCaprio’s performance as real life poet and helpless drug addicted Jim Carroll is so many things. One of the finest child performances I’ve ever seen, certainly. One of the most gut wrenching depictions of drug addiction ever captured, truly. And, of course, one of the actor’s most fearless roles to date. I’ll always respect the hell out of DiCaprio for bucking convention and playing such a raw character so early in his career.
4. The Wolf of Wall Street (2013)
as Jordan Belfort
It’s still early. Ask me in a year and DiCaprio’s relentlessly manic portrayal of real life stock broker Jordan Belfort could very well be ranked higher on this list. There isn’t a single moment in Martin Scorsese’s epic that DiCaprio isn’t fully on. A character this unapologetic about his gross excess should in no way be as appealing as DiCaprio allows him to be. But such is DiCaprio’s unique charm. I can’t say I ever really liked Jordan, but goddamn if I wasn’t sitting on the edge of my seat, eager to see what the hell he’d get into next.
3. Django Unchained (2012)
as Calvin Candie
I’m fascinated by reinvention. By an accomplished and well-known actor delivering a performance of sheer revelation. That was Calvin Candie, the charming and sadistic plantation owner who stole every one of his frames in Django Unchained. Who can forget Leonardo DiCaprio sitting at the head of a dinner table, sawing into the skull of a slave? The white entitlement, the abrupt rage, the overall conviction – as written, Calvin Candie is Quentin Tarantino at his most devilish. As played, it is DiCaprio at his most intrepid.
2. The Departed (2006)
as Billy Costigan
DiCaprio’s physical transformation as undercover cop Billy Costigan never gets mentioned enough. When we first meet him, he looks and acts like a little boy: thin, pale, and eager to prove himself. By the film’s end, he’s surpassed manhood and developed into a whithering shell of a man. Consumed by pills, lies, and constant torment, there is no limit to Billy’s anguish, no depth to his rage. I suppose what I appreciate most about this performance is that I really do like Billy, despite the fact that I disagree with many of his decisions. I always hope he’ll manage to wiggle his way out of the shitstorm he’s in, but, sadly, there’s no stopping that elevator’s descent into hell.
1. Revolutionary Road (2008)
as Frank Wheeler
From the moment I first saw Sam Mendes’ Revolutionary Road, I knew it contained the finest Leonardo DiCaprio performance I had ever seen. And I’m not sure I can fully explain why. It’s difficult to articulate how well DiCaprio understood Frank Wheeler. When I watch this film, I never see Leonardo DiCaprio, the movie star. I see Frank Wheeler, the tortured spirit. The neglectful father, the vengeful husband, the confused man. Kate Winslet is, of course, largely responsible for the strength of DiCaprio’s performance. The two played off one another so convincingly that to view their performances as separate entities simply doesn’t seem appropriate. I’ll be stunned if another DiCaprio performance ever tops this one for me. But I’ll always be looking. Admiring the fearlessness, hoping for a revelation.
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