25. Zoolander (2001)
Image Source: BBC
Zoolander the movie is an awful lot like its titular male model: Stupid to a fault, but also endearing and charming despite itself. Ben Stiller, who both directs and stars, understands the exact amount of effort needed to exert a story about models brainwashed as assassins for a shadowy cabal of clothing manufacturers. From A to Z, this spoof of a film. It picks apart our cultural fixation with fashion, thinness, celebrity, money, lust, sex, and power. It also benefits from a worthy villain in Will Ferrell’s high-strung Mugatu. His manic exasperation is fueled by being so aware of the absurdity of the world he inhabits. Zoolander could have been a forgettable comedy. Instead, it became a pop-culture staple.