4. SOME LIKE IT HOT (1959)

Why is cross-dressing so funny? Why is it so amusing to see men in dresses speaking in over-the-top falsettos, wearing fake boobies? Who cares. It's funny. And if it's done well, you have Some Like It Hot.

Often called the best comedy ever (and the highest ranking comedy on the American Film Institute's "100 Greates Movies" list), Some Like It Hot is a story about two poor musicians (Jack Lemmon and Tony Curtis) in the 1920s who accidentally witness the St. Valentine's Day Massacre. Chased by gangsters trying to get rid of the witnesses, Lemmon and Curtis dress up as women and join an all-girl band on its way to Florida. The lead singer of the band is Sugar Kane (Marilyn Monroe), and Curtis immediately falls for her. What ensue are lies, deceptions, more lies, and more deceptions, with Lemmon and Curtis vamping it up as women for virtually the entire movie.

What makes the movie good is not really its plot, but its exceptional dialog and one-liners. Every other sentence is a joke, and they keep building on each other. When Lemmon (as alter-ego Daphne) gets engaged to a lecherous old millionaire, Curtis can't understand it. He says "What are you going to do on your honeymoon?!" Lemmon thinks, and replies: "I'm leaning toward Niagra Falls…"

It's also famous for making Marilyn Monroe a star. Curtis once commented that she was such a pain to work with, that kissing her was like kissing Hitler. But watching the film, you can completely see why she became an icon. She's an amazing presence.

For 1959, this film was hugely subversive. There are so many gay subtexts to this film, that it's almost amazing to wonder how audiences back then didn't see it. But it just makes the film all the funnier now. And we have to say, it has the best last line of any comedy.

Notes:

  • Nominated for 6 Academy Awards (including Best Actor for Lemmon and Screenplay)

  • Won 1 Academy Award: Best Costume Design

  • It was shot in black and white because Lemmon and Curtis' make-up had a greenish hue

  • Placed #14 on the American Film Institute's "100 Greatest Movies" List