51. Some Like It Hot (1959)
When the American Film Institute made their list of the 100 Funniest Movies of All-Time, this Billy Wilder gem topped the list and with good reason. The screenplay, by Wilder and I.A.L. Diamond, is one of the cleverest scripts that utilizes the sight gag of men-in-drag to hilarious effect without becoming tired. The always charming Jack Lemmon and the marvelous Tony Curtis play two bandmates who accidentally witness the St. Valentine's Day massacre. To hide from the mob that is now chasing them, they dress as women and join an all-girl band on tour down in Florida. The hilarity, in addition to coming from the male-in-female-clothing angle, also comes from the potential love story as Curtis' saxophone player falls for the lead singer of the band (played delightfully by the extremely sexy Marilyn Monroe). The antics are classic (especially Jack Lemmon's female alter-ego being wooed by a millionaire) and the performances are comedic legends. Wilder, who was just as good at directing dramas (like Sunset Boulevard and Double Indemnity) as he was at comedies (like this one and The Apartment), gives his cast the perfect words and the perfect direction. He proved himself over and over again as a master writer-director in Hollywood. This film belongs in anyone's catalogue and is a great movie for the halfway point on our list!
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