5. Pootie Tang
When youre talking silly, they dont come much sillier than Pootie Tang. A Blaxploitation-James Bond parody thats shot with an eye towards live-action animation, Pootie Tangs sub-eighty minute running time is packed to the gills with bizarre and nonsensical characters and sequences. This includes: a main character who speaks entirely in gibberish (Sine Yo Pitty on the Runny Kine) that everyone understands regardless, Chris Rock getting beaten to death by a gorilla, and Wanda Sykes unceasingly dancing on street corners, a la Rosie Perez in the Do the Right Thing opening credits. But it might surprise you to learn that Pootie Tang was conceived, written and directed by none other than comedy mega-genius Louis CK. CK has come into his own as the perhaps the greatest stand-up comic currently, well, standing up, and as the auteur behind the brilliant FX sitcom Louie. While PT isnt up to those standards, it shows in rough form the same deconstructive approach to the world that his later triumphs would perfect. Pootie Tang, the film and character, is CKs exploration and dissection of the entire culture of cool. After all, what the hell is cool, anyway? Its an endlessly fluid term, constantly morphing at the behest of mass culture. How often do we look back at something that was once so popular, and gasp at the inanity of it. (Try watching a re-run of Saved by the Bell and see how long you can take the pastels before your eyes start to bleed. Go ahead, try.) What CK did is push the notion of cool so far, into a world so dissociated from our own, that it becomes straight-up gibberish. Pootie Tang, the character, is every Blaxploitation ideal cranked up past eleven. That point gets lost in the studio-mandated silliness, but its there all the same.