Born in Connecticut and raised in Atlantic Highlands, New Jersey, Anderson attended Henry Hudson Regional High School, with his friend, aspiring writer Kevin Smith; they graduated in 1988.
While Anderson was working at AT&T, Smith was working on his debut movie Clerks. As a joke, Anderson auditioned for the role of "Jay,"[citation needed] and based on this audition, Smith later offered Anderson a lead role as video store employee Randal Graves, a foul-mouthed apathetic slacker, who patronized, angered, and mocked his customers while avoiding any real work opportunities.
For his role in Clerks, Anderson was nominated for an Independent Spirit Award for Best Debut Performance.

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