As a teen, he popped up on both the big and small screen before landing on the moderately successful Married... with Children rip-off sitcom Unhappily Ever After. During his tenure, Connolly directed a number of episodes and went on to helm the Sundance-screened short Whatever We Do. But it was the Hollywood-insider dramedy Entourage that turned him into a bold-face name. Playing an up-and-coming movie star's manager and lifelong friend, Connolly flexed his dramatic and comic muscles and showcased his sex appeal, which also helped him land hotel heiress and celebutante Nicky Hilton off screen.