Some Like it Hot (1959)

 This film just proves that love has no boundaries. 

Musicians Jerry (the brilliant Jack Lemmon) and Joe (Tony Curtis) are constantly down on their luck, some through their own making (Joe loves gambling before paying the bills) and some through crazy circumstance as it is Chicago during the prohibition. They escape the claws of death so many times as, despite all their stupidity, they are clever. 

Disgusted as women, they flee to Florida but Sugar Kane (Marilyn Monroe) is also in the band and complicates things for the two men immensely. Naturally, she's beautiful and talented and both Daphne (Lemmon) and Josephine (Curtis) fall in love with her but once they arrive in Florida, a wealthy divorced, older man, Osgood (Joe E. Brown) latches himself onto Daphne and eventually even Daphne falls under his spell and accepts his proposal without thinking of the complications it would bring. And Joe has yet another disguise of his own to get Sugar to finally fall in love with a man though this one isn't good for her just like all the others. There is tons of brilliant dialogue and sticky situations throughout, and an ending that cannot be forgotten, and the acting just happens to be top-notch also.

Now, while the film has not dated the best, as you have two straight men disguised as men, not because they are struggling with their sexuality but rather because they feel that it is a necessity for them, and this creates numerous awkward situations (as it was designed) but all that aside, this film only further cements why Billy Wilder was a true genius. Grade: A-

Side Notes:

-Jack Lemmon was only one in the cast who received an Oscar nomination for his multi-layered performance and he was clearly the best (why is his greatness largely forgotten today?), though Monroe was great also. She was a much better actress than given credit for, just great in the painfully awkward to watch Bus Stop. 

-The costumes and lightning are great. Nothing in this film was done by accident.

-Despite the prohibition being present, there is a lot of alcohol drunk in this film.