It's 1929 in Chicago. Penniless friends and musicians Joe (Tony Curtis), a risk-taking saxophonist, and Jerry (Jack Lemmon), a more cautious double bass player, narrowly escape a police raid on an illicit nightclub run by mobster "Spats" Colombo (George Raft). Still reeling, Joe and Jerry are next unwilling witnesses to a St. Valentine's Day-type massacre perpetuated by Spats on informant "Toothpick" Charlie (George E. Stone) and his men. Desperate to leave town to avoid Spats' wrath, Joe and Jerry dress up as women, adopt the personas of Josephine (Joe) and Daphne (Jerry), and join an all-girls music band heading to Miami.
Jerry: [in high heels] How do they walk in these things, huh? How do they keep their balance?
Joe: It must be the way the weight is distributed. Now, come on.
Jerry: It's so drafty. They must be catching cold all the time, huh?
Joe: Will you quit stalling? We're gonna miss the train.
Jerry: I feel naked. I feel like everybody's staring at me!
Joe: With those legs, are you crazy? Now, come on.
[They see Sugar Kane]
Jerry: Look at that! Look how she moves. That's just like Jell-O on springs. She must have some sort of built-in motors. I tell you, it's a whole different sex!
Joe: What are you afraid of? Nobody's asking you to have a baby.
Jerry: Dirty old man...I just got pinched in the elevator.
Joe: Now you know how the other half lives.
Jerry: Look at that. I'm not even pretty.
Joe: They don't care. Just so long as you're wearing a skirt. It's like waving a red flag in front of a bull.
Jerry: Really. Well I'm sick of being the flag. I want to be a bull again.
Osgood: You must be quite a girl.
Daphne: Wanna bet?
With the 1950s about to turn into the 1960s, Wilder and Diamond push the boundaries of sexual innuendo well past typical expectations for the era. With the plot device of an all-girls band providing the excuse for plenty of barely-dressed women to parade past Joe and Jerry in drag, Wilder deploys Marilyn Monroe as his weapon of mass distraction. Although apparently a horror on the set due to pill addiction, Monroe has never looked or acted better as the explosively innocent woman unaware of her impact on men. As an added bonus she also performs three songs at her breathiest best. For most of the second half of the film Wilder dresses her in daring possibly see-through dresses (impossible to tell in black and white) with just enough coverage to get past the censors.
Junior: I'll say. I had two ponies drowned under me.
And with Joe-as-Junior pretending to have lost interest in women and daring Sugar to cure him on Osgood's yacht, she needs no further invitation to unleash all her expertise to get a rise out of the millionaire of her dreams. Meanwhile, back on shore Jerry-as-Daphne and Osgood dance up a storm all the way until dawn to the tango tune of La Cumparsita, and in the morning Jerry is quite convinced that he will be marrying Osgood.
Jerry: Have I got things to tell you!
Joe: What happened?
Jerry: I'm engaged.
Joe: Congratulations. Who's the lucky girl?
Jerry: I am!
Jerry: Osgood proposed to me! We're planning a June wedding.
Joe: What are you talking about? You can't marry Osgood.
Jerry: Why, you think he's too old for me?
Some Like It Hot has fun at the expense of both genders and all ages. The film ends with a classic exasperated admission that while love can be hot and messy, no relationship and no one sex is perfect, which is exactly why there is so much fun to be had.
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