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One not mentioned yet that I remember was a short lived 60s TV show called "The Ugliest Girl in Town." (Yes the title was politically incorrect, but it was the 60s after all.) It starred Peter Kastner doing drag a la the much later Tootsie. I remember as an early teen, and early CD, sneaking off to our second TV (in the kitchen no less) and being memorized by this guy openly wearing women's clothes. I wanted to be him. Peter's star was on the rise when he accepted the role of Tim/Timmie. When the show quickly closed Peter never again saw a starring role. Sad really. You can find a few early episodes on YouTube, if you are so inclined.
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Lana Mae, I so remember that cartoon in Playboy and think about it everytime that song is sang around Christmas Time
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For me it was probably Milton Berle and Flip Wilson. I remember mostly Flip Wilson as he went all the way with the dressing up including panties.
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I guess that Flip Wilson was the first that got my attention due to the fact that he went all the way besides just being so entertaining. As for seeing a real CD I go back to the 70s when my wife and I went to Finocchios in San Fran while exploring the west coast. I was mesmerized by that show for days.
For a local memory, I remember seeing a pretty well dolled up CD shopping in Frugal Fannies in MA while shopping for some cloths in the 80s. I don't remember the details but she really got my attention and I did my discreet best to follow her without drawing attention.
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Like many have said, my first exposure must have been Milton Berle, then Flip Wilson and of course Benny Hill. Other vivid memory are Jack Lemon and Tony Curtis in Some Like it Hot.
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Definitely Monty Python for me. Where I grew up PBS was a VHF channel (13), so I was raised by British television.
