What are some songs about transvestites?

Sweet Transvestite – RHCP. :)

Well, the classic Monty Ptython tune I’m a Lumberjack with the brilliant Eric Idle.

kevin barnes of of montreal‘s stage persona (or whatever) is a she-male, if that’s what you’re looking for. haha
i’m thinking you could find some interesting ones by of montreal. the one that comes to mind is wicked wisdom.
“I’m just a black she-male. And I don’t know what you people are all about”

do you teach a class? it sounds like one i’d love to be in haha

Ew at the term “she-male.” Not usually one that people choose to self-identify with!

Anyway. I love wikipedia lists. This isn’t specifically cross-dressing-related, but there’s some stuff included:
http://en.wikipedia.org/wiki/Category:LGBT-related_songs

I think Antony and the Johnsons have a few related tunes, possibly Baby Dee too.

Yeah…she-male is more about porn and less about people.

speaking of drag queens, what about Frankenstein Drag Queens from Planet 13 :)

Lola, kinks, (maybe) and Take a wallk on the wild side..by velvet underground guy.