Alan Hale's aspirations to become an opera singer ultimately led him to pursue a career in filmmaking, as his initial venture did not yield the desired outcome. He swiftly gained popularity as a supporting actor, starring in numerous films for the renowned director Cecil B. DeMille and even directing a few projects for him. With the advent of sound in the film industry, Hale transitioned to playing lead roles in a few movies, only to eventually settle into a successful career as a character actor.
Hale became one of the most prolific character actors of his time, and he was a prominent member of the "Warner Brothers Stock Co.", a group of talented actors and actresses who appeared in numerous Warner Bros. films during the 1930s and 1940s. His most iconic role is arguably his portrayal of Little John in the 1938 film The Adventures of Robin Hood, a role he reprised in two other films: Robin Hood (1922) and Rogues of Sherwood Forest (1950). His long-standing friendship with Errol Flynn led to collaborations on several projects, including the aforementioned The Adventures of Robin Hood.