Some Like It Hot - Billy Wilder, 1959

 

It’s my guess that back in 1959 America, cross-dressing was so personally threatening, the need to laugh it off could get an audience to sit through 120 minutes of giddy horse play. Nowadays, not so much. It was nearly impossible to watch, despite the very watchable faces of Jack Lemmon and Marilyn Monroe. 

 For males,  the threat is that if they didn’t dress like men, they would no longer qualify as such - and as the story advances, it becomes ever more clear that not only does the Jack Lemmon character look better as a woman, but eventually he’d rather be one so he could marry a millionaire and be taken care of. As his boyfriend makes clear in the final scene: “ nobody’s perfect” - i.e. his cisgender is no problem.   And given his growing submissiveness to his roommate, it should be no problem for him either. His only reason for dating the old money bags was to accommodate his roommate’s attempt to tryst with Sugar (Marilyn Monroe) on the rich man’s yacht.  

 By contrast, the masculinity of that roommate is never doubted. If it wears a skirt, he’ll take it for what it’s worth - and what is worth more than a passionate (if pathetic), Marilyn Monroe: desperattion for love and money and anything that helps her escape her cheap, disreputable life. Can’t see how any of this is humorous. And it only hints at what a comedy like ”Transparent” will make explicit 60 years later.

It might have worked much better as a 20 minute short,

like Laurel and Hardy made thirty years earlier.