how many films did Alan Hale play Robin Hood’s strapping sidekick Little John? July 6, 2017 By Show answer Three – in the 1922 silent film Robin Hood, starring Douglas Fairbanks; in the 1938 film The Adventures of Robin Hood, with Errol Flynn in the title role; and in the 1950 film Rogues of Sherwood Forest, featuring John Derek as the son of Robin Hood. More Entertainment QuestionsMore Movies Questions