Cummings started his acting career in his late teens on Broadway with the legendary Lillian Russell. He entered into movies in 1909 and quickly became a popular leading man. Few of the films he made as an actor are easily available, except for Buster Keaton's first feature film, The Saphead (1920), in which Cummings plays a crooked stockbroker. Around that time, he started to direct action movies and occasional comedies.