Though Perry was still in high school, it rapidly became apparent that his education would take a backseat to acting. While in a restaurant, he was spotted by director William Richert, who offered the 16-year-old a small role opposite River Phoenix in A Night in the Life of Jimmy Reardon (1988). Though Perry wanted to become a successful professional actor, his father was pressuring him to attend U.C.L.A. As a compromise, Perry agreed that if he could not find an acting job in the first year after high school graduation, he would attend college. Not long after that, he was hired by Fox television to star in the series Boys Will Be Boys. The series bombed, but Perry was then starred opposite Valerie Bertinelli in a new series, Sydney. While this show too was short-lived, it started Perry on a professional guest-star career that would land him roles on such series as Beverly Hills 90210, Growing Pains, and his father's show 240 Roberts. He made his sophomore film appearance in She's Out of Control (1989) opposite Ami Dolenz and Tony Danza. In the early '90s, Perry and his colleague, Andrew Hill, penned the pilot to a situation comedy about a bunch of friends in their twenties who like hanging out. They called their show Maxwell House and sold it to Universal. They pitched the idea to NBC, but the network had a similar vehicle in the works. Instead of taking Perry and Hill's show, they offered to co-star Perry in their program, Friends. The first episode aired in 1994 and became a Top Ten hit. In features, Perry had his first major success with the romantic comedy Fools Rush In (1997).