Some Like it Hot (1959)

One of the best comedies ever? I don't know, you decide. It was directed by Billy Wilder, of course, and it does feature two cross dressing men (Jack Lemmon and Tony Curtis) and a very sexy (redundant?) Marilyn Monroe. Lemmon & Curtis are two musicians who witness the St. Valentine's Day massacre, and have to change their appearance to stay alive. They join a troupe of performers (including Monroe) leaving on a train for Florida (really the Hotel del Coronado, near San Diego), but still have trouble avoiding the mob. Great supporting cast includes George Raft, Pat O'Brien, and Joe E. Brown (don't miss the end!) among others. Oscar nominations for Lemmon and Capra, for his direction and Screenplay Writing. Added to the National Film Registry in 1989. #1 on AFI’s 100 Funniest Movies list. #14 on AFI’s 100 Greatest Movies list. Brown's response to Lemmon's "Well, nobody's perfect." is #48 on AFI's 100 Greatest Movie Quotes list.

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