Pearlman's acting career commenced with a submission to a contest hosted by the website Funny or Die, subsequently earning him an audition opportunity for a role in The Virginity Hit. This "documentary style comedy" film chronicles the experiences and escapades of a group of friends as they strive to lose their virginity, boasting a unique approach where the directors provided Pearlman and his castmates with cameras to capture many of the scenes themselves, thus amplifying the realism of the movie.
Pearlman's television career commenced with his portrayal of Leslie Kaczander in the season 1 finale of Breaking In. In 2012, he took on the role of Jay in the American remake of The Inbetweeners. Furthermore, Pearlman lent his voice to Snotlout Jorgenson in Dragons: Riders of Berk, succeeding Jonah Hill in this position.
