After working in Chicago for several years and studying theater arts at Northwestern University, Conrad pursued an acting career. One of his first paying roles was a week-long job posing outside a Chicago theater where the film "Giant" (1956) was screened; Conrad bore a resemblance to the film's lead, actor James Dean, so his mother used her entertainment industry contacts to help him get the part intended as a publicity stunt to boost attendance at the theater. Conrad also studied singing; his vocal coach was Dick Marx, the father of singer Richard Marx.