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.
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.