17. Derek Zoolander, Zoolander (2001)
Played by: Ben Stiller
Zoolander is adored by many, and we can see why: Male models deserve to be mocked. But Ben Stiller’s performance as the titular idiotic pretty boy is so extra that it begins to wear thin at the film's halfway point. He’s a spiky-haired quote machine, which is good for a few laughs, but that actually proved to be a bad thing when, in the years following the movie’s release, nearly everyone with the ability to speak did an obnoxious Zoolander impersonation, presumably to annoy us. No doubt the character was written to be irritating, so in that respect we have to give props to the portrayal. But even Stiller, who must have had Derek Zoolander quotes yelled at him a zillion times, would probably concede that he was too successful at it.