Monsieur Verdoux (1947) (b/w, Criterion Collection)

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Charlie Chaplin plays shockingly against type in his most controversial film, a brilliant and bleak black comedy about money, marriage, and murder. Chaplin is a twentieth-century Bluebeard, an enigmatic family man who goes to extreme lengths to support his wife and child, attempting to bump off a series of wealthy widows (including one played by the indefatigable Martha Raye , in a hilarious performance). This deeply philosophical and wildly entertaining film is a work of true sophistication, both for the moral questions it dares to ask and the way it deconstructs its megastar`s loveable on-screen persona.