Zoolander

Directed and co-written by Ben Stiller, who stars as dimwitted male model Derek Zoolander, the film reached theaters on September 28, 2001 — about two and a half weeks after the September 11 attacks, a brutal moment to release a comedy about the fashion industry. Owen Wilson played rival model Hansel, Will Ferrell the absurd villain Mugatu, and Christine Taylor the reporter Matilda; David Bowie appeared as himself to judge a climactic walk-off. The character predated the film, born in short films Stiller made with writer Drake Sather for the VH1 Fashion Awards in 1996 and 1997.

The release stumbled. Reviews were mixed — Roger Ebert gave it one star, blaming the post-9/11 timing in part, a judgment he later privately apologized to Stiller for — and the film grossed a modest $60.8 million worldwide on a $28 million budget. Then the 2000s did their work: through relentless cable reruns and DVD nights, Derek's signature looks "Blue Steel" and "Magnum" became schoolyard and dorm-room shorthand, and half the script passed into everyday quotation.

By the end of the decade Zoolander was undisputed cult canon — enough that a sequel finally arrived in February 2016, to reviews that mostly proved the original's lightning couldn't be re-bottled.