After high school Outerbridge enrolled at the University of Victoria to study acting. Afterwards he toured Canada for four years with the theatre group Way Off Broadway. In 1997 and 2002 he was nominated in the Canadian Genie Awards as the best actor in the films Kissed and Marine Life, respectively. He was also nominated in the Gemini Awards for his achievements. Outerbridge won a 2013 Canadian Screen Award for Best Performance by an Actor in a Featured Supporting Role in a Dramatic Program or Series for his role in John A.: Birth of a Country.