Some Like It Hot (1959)

Trailer

Nobody's perfect.
So basically: During the 20's, two musicians, a bass named Jerry and a tenor sax named Joe, witness a shooting and have to get out of Chicago. One of their agencies is actually looking for a tenor and a bass, but female musicians. Desperate, the two dress in drag and hop on the train taking the all-female band to Florida.

Billy Wilder is definitely one of the most brilliant people in cinema. He has too many movies on the list to even count - in my head, anyway - and each one if pretty brilliant itself. But none come close to the awesomeness of Some Like It Hot. This movie is a crime drama, a comedy, and a romance, with a little bit of music mixed in. Oh! Did I mention the drag? Who wouldn't want to see Tony Curtis and Jack Lemmon - amazing actors, btdubs - in dresses? And Marilyn Monroe is totally hot. Best part? Tony Curtis' impression of Cary Grant! I was literally dying with laughter - you have to have seen Cary Grant movies to get the extend of the hilarity, tho.

This should be way higher on the list.

Ziggi seal of approval!