Although born in London, Cowan was brought up in Colchester, Essex. He is the son of a consultant physician and a charity worker, and has a younger brother and sister.Cowan boarded at Uppingham School in Rutland. He later obtained a first class degree
After securing a place to study English Literature at Trinity College Oxford, Oliver became actively involved in the university’s dramatic society. Upon graduating he was awarded a scholarship to train at the London Academy of Music and Dramatic Art (LA