Simpson reportedly prospected for gold in Alaska in his youth. By 1909 he had gone into the theatre. He appeared in at least two plays on Broadway between 1909 and 1912. He made his motion picture debut in Cecil B. DeMille's 1914 original movieversion of "The Virginian". He only had a minor role in that movie. By 1923, when the movie was remade, Simpson had progressed to playing the lead villain. 