I tried to rewatch John Tucker Must Die as something to have on in the background the other night, and wooow did that not hold up. I only made it to where they give him estrogen (which is insane and terrible) and he starts acting like a stereotypical “girl on her period” before I bailed. So many of the movies targeted at teenagers and young adults in that era are so bad. They went all in on punching down, and the amount of rape and sexual assault is wild in retrospect.
There are so many examples of anti trans sentiment in older comedy. Just about all of them hinging on the “you can always tell” myth and/or highlighting how obviously wrong and confused the poor trans people must be. For someone whose only exposure to trans people was that for a long time, I can’t begin to say how damaging and limiting that was.