Outerbridge, together with two older sisters and two older brothers, grew up in Toronto, Ontario. While his father practiced law, his mother studied piano at the Royal Conservatory of Music. He comes from a family of artists, as his uncle (though not by blood) was opera singer Jon Vickers, and his cousin Billy is a regular at Stratford. In Outerbridge's own words, with his father being a trial lawyer, there were a lot of theatrics on his paternal side as well.Outerbridge began his acting career after high school, when he enrolled at the University of Victoria to study acting. After graduating in 1988 with a Bachelor of Fine Arts, he co-founded the theatre group Way Off Broadway and toured Canada with them for four years. In the early 90's, he started out in television, and his early credits include shows such as 21 Jump Street or The Commish. First feature films include Paris, France and Cool Runnings.His talent was recognized early on, when roles in Marine Life or Chasing Cain earned