Obsessed, as usual

I'm a little bit obsessed with the presence and portrayal of cross-dressing and transgender folks in the media and popular culture icons. What about literature, also? I feel like I have to read all the classics again; are transsexuals always prostitutes in literature? I'm pretty sure there is more to find. Is there any big-big classic piece slightly talking about cross-dressing? I can imagine this being a topic among the Victorians. The Romans, maybe? I'm not surprised, though, at the intensity of this interest. This is really who I am: all my research as a history student was on representation, otherness, that sort of stuff. Identity construction, yes, but more on the artistic representation of "others." A lot of image-based analysis. What happens is that I ended up reading my own context through the same lens. I over analyze the PR industry, music videos, commercials, advertisement on the public transportation...
Below, two videos: Fey (so 90s!) and Gloria Trevi. In Spanish, sorry, but I'm not so sure you really need to understand the lyrics, and most of Americans can deal with some Spanish anyways. I said I'm obsessed with this, so it is for sure I'll be posting about English-based stuff soon.


Oh, wait! I'm so cool that I found it with English subtitles ;)
A word about G.Trevi: she got involved in really, really messed up stuff, and then spent several years in jail. And then, this song came. It was weird, this song to be her "comeback." I think she saw a thing or two in jail.