The Essentials: Leonardo DiCaprio’s 10 Best Performances

“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.