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1. 'Some Like It Hot' (1959)
Marilyn Monroe giving one of her finest comic performances. Tony Curtis lacerating his own image as a lady's man. Jack Lemmon offering up a taboo-shattering portrayal of someone whose disguise becomes his real face. And stirring the pot, Billy Wilder at the absolute height of his powers. This movie would be sophisticated in its take on gender roles if it were released right now, so I can only imagine that it looked like a movie from outer space when it was released in the '50s. None of the gender-bending comedies in the decades since this one have ever hit the mark this precisely, and real-life on-set friction seems to have given this an extra spark that makes it feel special. And the last exchange of dialogue in the film? Hilarious, heartbreaking, progressive, and real, and the perfect capper to an all-time classic.