Yeah, a lot of comedy from back in the day wasn't about emasculating men but mocking the idea of men in dresses. The late Barry Humphries best known for playing Dame Edna plain out said "Gender Affirming Care" was self-mutilation his native city of Melbourne took his name off a comedy award over saying that truth.
I do agree with Chappelle there has been an emasculation of men in Hollywood, but it wasn't men in dresses IMO it was stiff like the evolution of the sitcom dad. Look at the shows that started in the 80's like Family Ties, Wonder Years, Roseanne, Different Strokes, Cosby Show, Growing Pains, Alf, Doogie Howser, My Two Dads, Punky Brewster, Gimme A Break, etc the dad's where all competent men as were the moms then look at any sitcom that started in the mid 90's onward the dads are always dimwits married to smarter women. It's rare to find a smart dad in sitcoms anymore I think the Middle and Young Sheldon are the only two I can think of in recent years.
Edit: Red was smart too but that was probably because the showrunners knew not to fuck with Clarence Boddicker.