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Zoolander (2001)

In 2001, we were blessed with the comical duo of Ben Stiller and Owen Wilson, who have appeared in 13 films together over the past 20 years: Startsky & Hutch (2004), the Meet the Parents trilogy, two Zoolander films, and The Royal Tenenbaums by Wes Anderson. In this utterly hilarious film, viewers follow the adventures of male model Derek Zoolander, played by Stiller, who becomes brainwashed by one of the most ill-intentioned figures in the fashion world. Featuring cameos from David Bowie, Milla Jovovich, Tom Ford, Natalie Portman, and Lenny Kravitz, this film might have the most fashionable cast ever.