Some Like it Hot (1959)

If you’ve never seen Some Like it Hot, you should go do that. I’ll wait.

If you still haven’t seen it, Some Like it Hot is a classic cross-dressing comedy. Though it's not technically a gay movie, there's a male/male relationship, and lots of blurring of gender boundaries, with a lack of gay panic that would be refreshing today, let alone in 1959.

Two down on their luck jazz musicians witness the St. Valentine’s Day Massacre and go on the run, but can only find work in an all-girl’s orchestra, so they dress up as Daphne and Josephine and go to Miami. Joe/Josephine (Tony Curtis) sets about trying to seduce Marilyn Monroe, and Jerry/Dapne (Jack Lemmon) finds himself dating an elderly playboy millionaire. As the charade goes on, the Jack Lemmon becomes more absorbed in his Daphne persona, and the beta relationship progresses until gender becomes somewhat beside the point:

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!
Joe: WHAT?!
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?
Joe: Jerry, you can't be serious.
Jerry: Why not? He keeps marrying girls all the time.
Joe: But, you're not a girl! You're a guy, and, why would a guy wanna marry a guy?
Jerry: For security! Look, I know there's a problem, Joe.
Joe: I'll say there is.
Jerry: His mother - we need her approval, but I'm not worried because I don't smoke.
Joe: Jerry. There's another problem, like what are you gonna do on your honeymoon?
Jerry: We've been discussing that. He wants to go to the Riviera but I'm kinda leaning toward Niagra Falls.
Joe: My God.
Jerry: I don't expect it to last Joe. I'll tell him when the time's right.
Joe: Like when?
Jerry: Like right after the ceremony. Then we get a quick annulment, he makes a nice little settlement on me and I keep getting those alimony checks every month.
Joe: Jerry listen to me there are laws, conventions. It's just not been done.
Jerry: Joe this may be my last chance to marry a millionaire.
Joe: Oh, Jerry — Jerry, will you take my advice? Forget about the whole thing, will ya? Just keep telling yourself: you're a boy, you're a boy.
Jerry: I'm a boy.
Joe: That's the boy.
Jerry: I'm a boy. I'm a boy. I wish I were dead. I'm a boy. Boy, oh boy, am I a boy. Now, what am I gonna do about my engagement present?
Joe: What engagement present?
Jerry: Osgood gave me a bracelet.
Joe: [examining it] Hey, these are real diamonds!
Jerry: Of course they're real! What do you think? My fiance is a bum?

Director Billy Wilder couldn’t figure out how to end the film, so the actor improvised the final line as a placeholder until someone could write something better:



As if that's not enough, it was rated C for Condemned by the Catholic Decency League, and was banned in Kansas City. So you know they did something right.