Hollywood lost one of its true greats in 2008, when Sydney Pollack passed away from cancer. Though he was a filmmaker first—directing 20 films and producing more than 40 for the likes of George Clooney and Pollack's longtime business partner Anthony Minghella (who passed away at the age of 54 just two months before Pollack)—Pollack clearly understood the art of performance.

In addition to directing a dozen actors to Oscar nominations, Pollack made some powerful statements of his own in front of the camera, working with the likes of Stanley Kubrick (Eyes Wide Shut) and Woody Allen (Husbands and Wives). But his best role was in a film of his own: 1982's Oscar-winning Tootsie. Pollack's creative differences with Dustin Hoffman on the set led to Hoffman's suggestion that Pollack play the role of George Fields, an acting agent fed up with Hoffman's antics. The result is pure brilliance.