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Charlie Chaplin's talented brother Sydney enjoyed moderate box-office success as star of a series of Warner Bros. features in the late 1920s. Sydney's Fortune Hunter was based on a play by Winchell Smith, which had starred John Barrymore on Broadway and which had previously been filmed in 1914 with William Elliot in the lead. Chaplin plays Nat Duncan, an impoverished socialite who hopes to land a rich spouse. His partner in "crime" is his pal Handsome Harry West (Duke Martin), who intends to share the monetary rewards of Nat's marriage. The plan is scotched when Nat falls for just-getting-by soda shop owner Josie Lockwood (Helene Costello). The film's best bit finds the lovestruck Nat subbing for Josie at the soda fountain; when a customer asks for a cigar, the absent-minded hero begins peeling the stogie like a banana. The Fortune Hunter was directed by Charles Reisner, who cut his cinematic teeth as an actor/assistant with Charlie Chaplin's First National unit in the late teens.