When Zoolander premiered in 2001, it arrived as a silly diversion—a low-stakes comedy about male models and a fictitious assassination plot. However, in the two decades since its release, Ben Stiller’s directorial effort has proven to be a surprisingly enduring piece of satire. While on the surface it parodies the vanity and vapidity of the fashion industry, Zoolander succeeds as a lasting comedy because it functions on multiple levels: it is a sharp takedown of corporate capitalism, a surprisingly earnest coming-of-age story, and a masterclass in the specific genre of "stupid-smart" humor.