Stiller was born in New York City. Stiller's father is Jewish and his mother, who is of Irish Catholic background, converted to Judaism after marrying his father.[3][4] His parents frequently took him on the sets of their appearances, including an appearance on The Mike Douglas Show when he was six.[5] He admitted in an interview that he considered his childhood unusual: "In some ways, it was a show-business upbringing—a lot of traveling, a lot of late nights—not what you'd call traditional."[6] His older sister, actress Amy Stiller, appeared in his movie Dodgeball in a short scene as a waitress at a restaurant.[7] He displayed an early interest in film making and made Super 8 movies with his sister and friends.[5] At 10 years old, he made his acting debut as a guest on his mother's television series Kate McShane. In the late 1970s he performed with NYC's First All Children's Theater in several roles, including the title role in Clever Jack and the Magic Beanstalk. After being inspired by the television show Second City Television while in high school, Stiller realized that he wanted to get involved with sketch comedy.[8]
After he graduated from the Calhoun School in New York in 1983, he enrolled as a film student at the University of California, Los Angeles and joined Beta Theta Pi fraternity.[9] After nine months, Stiller left school to move back to New York City. He made his way through acting classes, auditioning, and trying to find an agent.[10]
He landed a role in the Broadway revival of John Guare's The House of Blue Leaves, alongside John Mahoney, a play which later garnered four Tonys.[10] During its run, Stiller produced a satirical mockumentary whose principal was fellow actor Mahoney. His comedic work was so well received by the cast and crew of the play that he followed up with a 10 minute short called "The Hustler of Money", a parody of the Martin Scorsese film The Color of Money. The film featured him in a send-up of Tom Cruise's character and Mahoney in the Paul Newman role — only this time as a bowling hustler instead of a pool shark. The short got the attention of Saturday Night Live, which aired it in 1987, and two years later offered him a spot as a writer.[10] In the meantime, he also had a bit part in Steven Spielberg's Empire of the Sun.
In 1989, Stiller wrote and appeared on a season of Saturday Night Live as a featured performer. However, since the show did not want him to make any more short films for the show, he left after five shows.[10] He then put together Elvis Stories, a short film about a fictitious tabloid focused on recent sightings of Elvis Presley. The film starred fellow friends and co-stars John Cusack, Jeremy Piven, Mike Myers, Andy Dick, and Jeff Kahn. The film was considered a success, and led him to develop another film entitled Back to Brooklyn for MTV, a music video cable television network.