Dillon auditioned for a role and made his debut in the film. Another of Dillon’s early roles was in the Jean Shepherd PBS special The Great American Fourth of July and Other Disasters. The only available copies of this film are stored at UCLA, where a legal dispute makes it unavailable to the public. in the early 1980s, Dillon also had prominent roles in three adaptations of S. E. Hinton novels: Tex (1982), The Outsiders (1983) and Rumble Fish (1983). All three films were shot in Tulsa, Oklahoma, Hinton’s hometown. Dillon had a 3-year relationship with actress Cameron Diaz in the late ’90s. He faced a maximum of one year in jail, and a fine of $1,000.