In 2000, Stiller starred in three more films, including one of his most recognizable roles, a male nurse named Gaylord "Greg" Focker in Meet the Parents, opposite Robert De Niro. The film was well received by critics, grossed over $330 million worldwide, and spawned two sequels. Also in 2000, MTV again invited Stiller to make another short film, and he developed Mission: Improbable, a spoof of Tom Cruise's role in Mission: Impossible II and other films.
Stiller dated several actresses during his early television and film career, including Jeanne Tripplehorn, Calista Flockhart, and Amanda Peet. In May 2000, Stiller married actress Christine Taylor at an oceanfront ceremony in Kauai, Hawaii. They met while filming a never-broadcast television pilot for the Fox Broadcasting network called Heat Vision and Jack. The couple appeared onscreen together in Zoolander, DodgeBall: A True Underdog Story, Tropic Thunder, Zoolander 2, Curb Your Enthusiasm, and Arrested Development. The couple have two children. In May 2017, Stiller and Taylor announced their separation in a joint statement, after 17 years of marriage.