Gold moved to Chicago after college where he performed as Michael in Jean Cocteau's Indescretions, Oak Park Festivals Much Ado About Nothing and Patrick Marber's Dealer's Choice. In May 1998, he landed the part of Ste in Jonathan Harvey's coming of age play Beautiful Thing at The Famous Door Theater in Chicago. Its success there brought the whole cast to the Cherry Lane Theatre in NY, where it opened to rave reviews in February 1999.