 His maternal grandmother had been an actress, starring with the famous actor Edwin Booth (brother of actor-assassin John Wilkes Booth).Sherman began his career as a child actor appearing in many touring companies.As an adult he appeared on Broadway in plays such as "Judith of Bethulia" (1904) with Nance O'Neil and in David Belasco's 1905 smash hit "The Girl of the Golden West" with Blanche Bates where he was a young Pony Express rider.