On arriving in California, Pitt studied under coach Roy London for six years. He first appeared in the sitcom Head Of The Class, for a while dating the show's star Robin Givens. He also guest starred in two episodes of Growing Pains. Pitt appeared as Chris in the long-running soap Another World. While auditioning for the show Our House, he was asked to read for another part, and found himself playing Shalane McCall's boyfriend Charles in Dallas. He also had a number of roles in prime time series such as thirtysomething, 21 Jump Street, and Freddy's Nightmares. Pitt appeared uncredited in both Less Than Zero and Charlie Sheen's No Man's Land before appearing in Cutting Class, about a maniac stalking cheerleaders. He began dating co-star Jill Schoelen.
In 1988, Pitt had his first starring role, in Dark Side Of The Sun, where he played a young American taken by his family to the Adriatic to find a remedy for a skin condition. The movie was shot in Yugoslavia in the summer of '88 with Brad being paid $1,523 a week for seven weeks. However, with editing nearly complete, war broke out and much of the film was lost. The film was released years later. Pitt won a part in the TV movie Too Young to Die?, about an abused teenager given the death penalty for murder. Pitt played the part of a drug addict, Silly Canton, who took advantage of runaway Juliette Lewis, who Pitt began dating in real life. "It was quite romantic", he later observed dryly "shooting her full of drugs and stuff". The pair would be together for three years.