The Masquerader
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The Masquerader is a 1914 film written, directed, and starring Charlie Chaplin. Its running time is only 16 minutes. It is the tenth film directed and the second written by Chaplin.
Spoiler warning: Plot and/or ending details follow.
Charlie is an actor, who messes up several scenes and is kicked out. He returns convincingly dressed as a lady and charms the director. However, Charlie never makes it into the film. The plot involving a guy dressing up as a woman is quite popular in old silent movies.
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