10. Some Like It Hot - Billy Wilder, 1959
Billy Wilder loved topping himself. Some Like It Hot topped his sex-romp The Seven Year Itch, which forever immortalized Marilyn Monroe’s sidewalk dress. It stars Tony Curtis and Jack Lemmon (Lemmon would go on to have a great report with Wilder, starring in the majority of his remaining films) with Monroe in the role the cemented her look and style for the rest of her life and legacy. The AFI called it the funniest American film of all time and it’s hard to argue with that.
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