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Hill then made a brief appearance in Judd Apatow's directorial debut The 40-Year-Old Virgin, which eventually led to him appearing in the role of a virgin video game tester in the comedy Grandma's Boy (2006) and starring in a larger supporting role in the Apatow-directed Knocked Up (2007).
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On television, Hill played the "RA Guy" on the first season of the Oxygen Network sitcom Campus Ladies.
He guest-starred in an episode of Clark and Michael.