Mushy

Which starred Nathan Lane as a drag queen just two years after he had voice Pumba in "The Lion King":

And we ESPECIALLY need to remember Victor Victoria from 1982 (during the REAGAN administration) which is SET IN THE 1930S and stars everyone's favorite curtain-sewing nanny as a struggling soprano who decides to pretend to be a boy doing drag (DOUBLE THE DRAG FOR YOUR MONEY). I mean look at this photo:

Count Victor Grazinski isn't putting up with your transphobia (or you being a dick to Robert Preston).

Some Like It Hot (1959), it got in trouble with censors and still went ahead, but it featured a lot of Gender and a character getting really into this whole “being a girl for real” thing, as well as the implication of a a gay engagement being on the table

but like? It has Marilyn Monroe in it and banger music and it’s a classic! I only know from my mother bringing it up and also a tiny bit of exposure to russian tv channels, but I think it was also popular in the Soviet Union? So she’d seen it as a child and loved it so much she watched it with me when I was also just a child.