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Stiller is the son of the comedians and actors Jerry Stiller and Anne Meara. He began his career writing mockumentaries and was offered a variety sketch series, The Ben Stiller Show, which he produced and hosted for its 13-episode run. The series ran on MTV in 1990 and  Fox in 1992 and 1993, earning him a Primetime Emmy Award for Outstanding Writing for a Variety Program. Stiller was a member of a group of comedic actors colloquially known as the Frat Pack.

Transitioning to acting in films, Stiller made his directorial debut with Reality Bites (1994) and went on to direct and star in films such as The Cable Guy (1996) and The Secret Life of Walter Mitty (2013). He also starred in a string of successful studio comedies, including Along Came Polly (2004), Dodgeball: A True Underdog Story (2004), Starsky & Hutch (2004), and Tower Heist (2011). His performances in independent films include Flirting with Disaster (1996), The Royal Tenenbaums (2001), and the Noah Baumbach films Greenberg (2010), While We're Young (2014), and The Meyerowitz Stories (2017).

Since the mid-2010s, Stiller has primarily worked as a television director and showrunner. In 2018, he directed the Showtime limited series Escape at Dannemora, earning a Directors Guild of America Award and two Primetime Emmy Award nominations for Outstanding Limited Series and Outstanding Directing for a Limited Series. In 2022, he was a director and executive producer on the Apple TV+ series Severance, earning two Primetime Emmy Award nominations for Outstanding Drama Series and Outstanding Directing in a Drama Series.