The original Zoolander was received positively by critics and fans alike. Its 2016 sequel, Zoolander No. 2, was reviewed poorly, as Stiller hilariously alluded to during his surprise onstage appearance. The actor and filmmaker has spoken openly about being surprised by the negative reaction to the sequel over the years.

"Zoolander" marked Stiller's third directorial effort, following 1994's "Reality Bites" and 1996's "The Cable Guy," starring Jim Carrey and Matthew Broderick. The actor starred in the film alongside several comedy all-stars, like Owen Wilson and Will Ferrell. The movie also features Christine Taylor, Stiller's real-life wife.