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Raised on Manhattan’s Upper West Side, Stiller is the son of comedians Jerry Stiller and Anne Meara. After leaving the University of California at Los Angeles in 1984 (he had been there only nine months), he made his acting debut in a Broadway revival of The House of Blue Leaves in 1985. Two years later, Stiller made his big-screen debut in Fresh Horses, starring alongside aging Brat Pack members Molly Ringwald and Andrew McCarthy. The fact that the film was a disaster didn't phase Stiller, whose next gig, in 1989, was as a writer for the sketch comedy show Saturday Night Live (SNL). He described the backstage atmosphere there as "very negative" and, disillusioned, left for Los Angeles after just five weeks as an SNL writer.
In Los Angeles, Stiller began work on The Ben Stiller Show, a half-hour sketch comedy that aired on MTV before being picked up by Fox for a brief run. Like the Saturday Night Live of the 1970s and 1980s, The Ben Stiller Show became fertile breeding grounds for young, hip comics. Bob Odenkirk, Andy Dick and Janeane Garofalo were among those who wrote or acted for The Ben Stiller Show. Despite the critics' fondness for the show Fox canceled it after just twelve episodes. Stiller and his cowriters did win an Emmy for outstanding writing in a variety or music program in 1993, after the show had already been canceled.
Stiller's next project was directing and acting in Reality Bites, a film about twentysomethings and their relationships and issues. Also starring Winona Ryder, Ethan Hawke, and Garofalo, and often seen as a glorification of Generation X and the values commonly associated with it, Reality Bites was unpopular with critics but became a minor cult classic. Stiller was to follow that project by directing A Simple Plan, but six weeks into production he had a falling out with Savoy Pictures over budget issues and abandoned the picture.
Stiller returned to acting on the big screen with the David O. Russell (Spanking the Monkey, Three Kings) comedy Flirting with Disaster, in which Stiller plays a young father searching for his birth parents. A very successful film on a relatively small scale, Flirting with Disaster was a hit with critics and financially successful. Stiller's next project was to direct the offbeat comedy Cable Guy, which starred Jim Carrey and Matthew Broderick. He followed Cable Guy with a starring role opposite Cameron Diaz and Matt Dillon in the extremely successful gross-out comedy There's Something about Mary (1998). The following year, Stiller cowrote the mock self-help book, Feel This Book: An Essential Guide to Self-Empowerment, Spiritual Supremacy, and Sexual Satisfaction, with Garofalo.
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