BookJumper: I know; it's fascinating, isn't it? I even remember a play where the heroine was played by a man pretending to be a woman disguised as a man. Recursive cross-dressing, in other words, and somewhat confusing. I can't seem to recall the name, though...
Kell: I had heard about Yentl the movie, but I had no idea it was based on a book! I read one of Amazon's reviews on it, and it seems as though neither of the two felt any attraction towards the other?
I've seen Victor/Victoria - and I loved it. Nora telling what's-his-name that King is "shacking up with another man" and his deadpan "run that by me again" makes me cackle everytime I see the scene.
Never did see Tootsie, though it did come up in my quest for genderbender literature and films - and with your recommendation, I don't think I have any other choice but to look it up!
Tipping the Velvet has also come to my notice before, but as the woman already knew that the heroine was a woman, it's much too far outside my search criteria to hunt down to buy :/
Raven: That book has been all but ubiquitous in my search; it's been popping up everywhere I look, tempting me into buying it. I haven't read too much by Pratchett, but I do enjoy his way of parodying the genre. I remember the heroine's name being from the sea chantey "The Handsome Cabin Boy", or some such.
Thank you for taking the time to make suggestions