 Hill then made a brief appearance in Judd Apatow's directorial debut "The 40-Year-Old Virgin", which eventually led to his appearing in the role of a virgin video game tester in the comedy "Grandma's Boy" (2006) and featuring in the comedies "Accepted" and "Click", playing Adam Sandler's character's son in the latter film.Hill was featured in a larger supporting role in the Apatow-directed "Knocked Up" (2007).On television, Hill played the "RA Guy" on the first season of the Oxygen Network sitcom "Campus Ladies".