Some Like It Hot (1959)

This film was denied approval under the production code then applying to motion pictures, due to its themes of cross-dressing and homosexuality.  When it became a massive commercial and critical success, it significantly contributed to the abandonment of the code and a freeing up of the kind of content that films could include.  And for that, I salute it.

Alas, although it's still a highly regarded comedy in most circles, I didn't much care for it.  I mean sure, the cast is good - Monroe, Tony Curtis and Jack Lemmon all know their stuff, after all.  But the script ... eh.  First of all we have the fact that our romantic lead (Curtis) is a character who we are supposed to find charmingly roguish, but is frankly the kind of man who thinks nothing of lying to and stealing from the women in his life.  Admittedly, he does eventually realise he's a no-good jerk ... but that of course just means that he gets the girl at the end of the film.  You know, the one he's been lying to all film.

Lemmon gets the comedy relief character, and he is good at the role.  But alas the "humour" is mostly based around the idea that it's funny that he spends most of the film pretending to be be a woman and being romantically pursued by an older man.  And yeah, I get that the film is nearly sixty years old and it was pretty brave to depict the concept at all, but it's still a case of "Homosexuality is so weird!".

Why is Lemmon's character dressed as a woman?  To hide out from gangsters.  You see, he and Curtis's character witnessed a mob murder.  Needing to get out of town and lay low, they dress up as women so they can join up with an all-female band that is heading to Florida.  Said band of course includes Monroe's character.  Shenanigans ensue.

I can see why this, the last film in this box set, was a success at the time of its release, but I can't really recommend it, personally.  Instead, I'd say if you wanted to sample Monroe's career, you'd be best served by seeing Love Nest (as an example of her pre-fame roles), Gentlemen Prefer Blondes (for Monroe the leading lady) and Niagara (for a real change of pace from her normal "dizzy blonde" routine).