In Shakespeare's time, female roles were played by boy actors. In opera up until the 19th century, female roles were taken by castrati when female singers weren't available or allowed (depending on jurisdiction). In both cases, the actors involved were seen sometimes as novelties, sometimes as necessary given the limitations of the art, and sometimes as talented performers in their own right.
Flash forward to the twentieth century, and female impersonation is the domain of the gay bar, a facility often illegal outright or de facto. I realize that I'm zooming between countries and centuries, but at some point there seems to be a switch flipped. Did the radical idea that women should be allowed in the arts push away liminal figures that were secretly only ever tolerated out of necessity? Did a greater emphasis on what we now call homosexual behavior stigmatize these figures? Am I talking out of my ass?
I know that Japanese theater has its own relationship with crossdressing, and that's all I know about Japanese theater's own relationship with crossdressing, so I'm limiting the question's purview to the West.
female roles were taken by castrati when female singers weren't available or allowed (depending on jurisdiction)
I was a little wiffy on if I was going to answer this, as it’s tangential to my zone, and this is a very wiffy history and I can’t tell you “It was March 1947 precisely when drag became drag,” but I have to answer now since you get mad propz for knowing your castrato history. :)
Okay so I’ve done a little reading on drag, and I can certainly point you in the right direction here. The main notion is that we have three things going on here unpacking the idea of drag. One, we have the historical practice of cross-dressing in high art that has a homosocial requirement for some reason, from Peking Opera to Italian Opera; two, we have the historical practice of cross-dressing in “low” theater or in the theater of the common folk; and three; we have cross-dressing for sexual or identity reasons, maybe private or maybe public, but outside of theatre. These different ideas coexisted more or less all at the same time in different societies, but the third type, more than anything, what society has really railed against. Consider we still make a pretty big space for “acceptable” cross-dressing for low and high art purposes, but struggle with the third kind. Versions of this goes on in many high schools in the US with no fuss about threats to the fragile development of teen boys’ masculinity, the only protests are that it is insulting to women. For higher art, this cross dressing is officially “culturally significant” per the US Government. We can even take Maxwell Klinger from M*A*S*H as the ultimate symbol of this divide: the character is engaging in cross dressing as a tool to (falsely) indicate he is homosexual, but no one takes his cross dressing as sincere, so he is accepted as straight. Yet, I think sneaking in on the 20 year rule since he’s pretty old now, Eddie Izzard used to get a lot of attention for his casual non-sexual and not-a-joke cross dressing. Basically theatrical cross dressing is the least sexually threatening because it’s “not real.”
So, long way around, what I’m saying is that the deviant/acceptable divide is not that firm, now or then! There wasn’t like, a dude in a dress at every pub in Elizabethan England and then blammo, suddenly the Western world lost its chill and started hating it. The times of theatrical crossdressing being in wide use still saw strict social attitudes and even laws against cross dressing. Consider a short century after Shakespearian cross dressing England saw the reign of the notorious Society for the Reformation of Manners, which did a lot of nasty things but famously actively persecuted men who have sex with men, and the easiest way to get charged with sodomy in 18th century England while not actively engaged in a sexual act was to be discovered in a molly house with a dress on. Meanwhile back in Italy at the same time, a young Neapolitan castrato wearing a dress on a Roman stage would have had a compatriot back home wearing a dress for a very personal reason, but the castrato would be be the more expressly sexual object, and the one getting sexually harassed from the church officials in the audience, unlike a femminiello. Also if the opera got revived in Naples, his female role would have been played by a woman, and if a good castrato couldn’t be hired for a provincial theater she could have easily pulled on some pants and taken a male role the next month. Nothing is simple with gender history…
Back to the gay bars though. Drag as we know it now (a performative gay act, humorous or titillating to your choice, but airing Mondays 8/9pm central, only on Logo) is pretty modern, and not thought to be a descendant of the theatrical work of Billy Shakes or the castrati, but instead either from the world of burlesque in the 19th century, or perhaps from the wider feminine heritage of some MSM/homosexuality/whatever avoids presentism/you know what I mean. It depends on who you read, and I can make an argument for either it being not connected to homosexuality until very recently (as the idea of gay identity is modern yada, but also because many theatrical uses were very impersonal for the actor) OR I can make you an argument that drag is the modern face of the very old tradition of some MSMs liking to express the feminine. I don’t really have a dog in the fight here, and it’s kinda a personal thing how you see the history of it I think, and how you do your own drag. In the immortal words of Lt. Col. Henry Blake on transvestism, I don’t like to pry into a man’s religion.
The history on this is kinda scattered in different places, but I will link you to this 2013 Master’s thesis, which I think has a good basic overview of the arguments, and I find it an interesting perspective because it’s a Dutch guy writing on American drag culture, and I really love reading non-American commentary on American life, it is my favorite. He argues the lowest point of acceptability for cross dressing was during the “Lavender Scare” through Stonewall, which I’d agree with, so it saw a sharp swing into being a very deviant and underground act say from 1945-1980. Before it certainly had more acceptance, when kept in its “correct” context of the theater.
I would be happy to expand on the idea of castrato bodies on stage, in and out of dresses, being both srs high art and “deviant” at the same time, but my lunchbox is calling for me with its siren song, so let me know and I’ll come back to it!