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Oh man. So many and so much. Most of the "comedy" from the 80s, 90s, early 2000s is unwatchable. Older movies are sometimes straight up disgusting. I think it's a sign for how we grow as a society to be more aware of the sexism, racism and other forms of disrespect that has been sold as comedy or just as "normal". I consume much more consciously and through a more meta lense. For reference: I'm turning 40 this year
I like to watch those old shows because they are reminders that we really have made significant progress in my lifetime.
Primary source materials, really. A great window into the past.
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.