I grew up in the 70s and 80s. Several of the shows from that era are now available to stream online. I'm watching the old Night Court, which I thought was hilarious in the 80s. But even then, they had an episode where Dan Fielding's best friend from college "became a woman." And there were a lot of cross-dressers on the show. Obviously they were poking fun a some of it, but the one where the dude had the surgery was quite surprising to see.
Hell, the "chick" in the Power Station (with Robert Palmer as lead singer) music video Some Like it Hot was a dude.
Right. “dude Looks Like a Lady,” The Rolling Stones “Some Girls” album etc, it was always a fringe.