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Tom Hanks had a TV show about two guys who wear women's clothes so they can live in a female only residence.
Ran from 1980 to 1982 and it was never a big deal with the Christian Nationalists then.
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Mr. Television, Milton Berle did drag; as did such popular stars as Flip Wilson and Jonathan Winters.
Never seen the show, but isn't this an instance where cross-dressing is seen as a gag and not necessarily an acceptable and normal thing to do?
As a needlessly serious answer - conservatives don't mind exceptions. What scares the shit out of them is any systemic challenge to The Hieararchy.™ Guys in dresses as a punchline doesn't ask them to reconsider how men and women are treated differently. Like asking why there's a female-only residence in the first place.
Have you ever watched "Some Like It Hot?" Marilyn Monroe, Tony Curtis, and Jack Lemon
It came out in 1959 and asked all the questions you brought up. Sailed past the censors and was popular on TV for decades
My opinion is that because it was a 'silly movie' it got to say things a 'serious' film would be condemned