16. Some Like It Hot
directed by Billy Wilder
“I say, you know what’s really funny?” One distinguished English gentleman says to his companion. “A man dressed in women’s clothing.” “Yes, quite,” his friend replies. “Ripping good laugh.” The proliferation of crossdressing-as-comedy is either a product, or the necessary cause, of its utter banality, yet Billy Wilder’s 1959 comedy has remained one of the funniest films ever made for nearly sixty years. It helps to have a plot silly enough to support it – Tony Curtis and Jack Lemmon are jazz musicians who need cash and a way out of town fast after witnessing the St. Valentine’s Day massacre, only to find their ticket in an all-female band about to board a train for Miami. That Marilyn Monroe is a member of said band has a way of making their fate more desirable, though wooing her becomes a bit more complex, what with all the stockings running about. And so further identities must be created, mistaken, and reappropriated, a flurry of screwball complexity that could only end with such a note-perfect shrug of the shoulders as Wilder ultimately offers.