3. The Assassination of Jesse James by the Coward Robert Ford - Jesse James
As Pitt became older, his roles have progressed from the young buck and into alpha male territory. Hes proved very capable too, whether playing professional furniture-flipper Billy Beane in Moneyball, the gleefully psychotic Aldo Raine in Inglourious Basterds or the always-eating Rusty Ryan in the Oceans series. Hes very comfortable in own his skin, and though these roles are all undoubtedly awesome, I would argue that hes not really stretching himself. But then theres The Assassination of Jesse James by the Coward Robert Ford. Apart from having a bewilderingly long title, it features a compelling subversion of the alpha male persona by Pitt. He plays the eponymous Jesse James, and is never anything less than skin-crawlingly watchable as the infamous outlaw. Though Casey Affleck waltzed off with most of the plaudits for this film, I truly believe that Pitts performance matches, if not surpasses it. Hes basically playing a tortured caricature of himself, if you trade out the acting for bank robbing. James is a character consistently in anguish, always keeping a dominating air even when all authority has been stripped from him by an ever-enclosing world. This unsettling performance proves to be the rudder guiding the film, with Pitt constantly keeping a bullying demeanour of forced joviality at odds with his increasingly parlous situation. He does a great job of it, portraying a man who behind every forced smile and over-friendly manner is becoming increasingly desperate- hes lived far too high for far too long and has started to doubt his own not-inconsiderable hype. The audience simultaneously feels both pity and disgust for him, and this is an incredibly hard trick to pull off. Effectively, Pitts entire role embodies the films musings on the cult of celebrity; that a man who was clearly capable of great deeds can quite easily succumb to egomania. He puts across this concept extremely well, wringing out most of the films drama before his own inevitable and tragic conclusion. To find the pathos in a monster meandering towards their own doom is very hard feat, and its a credit to Pitts considerable abilities that he manages it. Theres a reason he won the Volpi Cup for this one.