By his twenties, Simpson had grown into a hulking figure and considered a boxing career. He has been referred to in some sources as the 1935 "New York City Heavyweight Boxing Champion," but the only official records of his ring work are for two fights in Los Angeles in 1939, both of which he lost. Simpson, nicknamed "Mickey," arrived in Los Angeles in the late 1930s. Some unconfirmed stories have him working as a chauffeur for Claudette Colbert. In 1939, he reportedly played a tiny bit part in his first film, Stagecoach. The Director, John Ford, would loom large in Simpson's career.