Here's a fun game. Play it with your friends! Here's how it goes. Listen to this:
And try to guess the gender of the singer.
As it turns out, the singer is male, singing in falsetto. If you knew this, either your ears are much, much better than mine, or you've heard the song before! It's "This town ain't big enough for the both of us" by Sparks:
I don't know whether Sparks was (were?) trying to transgress gender boundaries here or not - I've never heard anything to that effect, but then again, look at that album cover! I suppose this could be a gender-ploitation sort of thing, but they seem to be playing fairly honestly. Here's the way I see the song:
A person (of indeterminate gender) wants to ask somebody out on a date. They're too afraid, so they don't - so they console themselves by repeating (to whom I'm not sure - other people? their fear? a stray dog?) the extremely stereotypically masculine staple of the Western, "This town ain't big enough for the both of us!", all the while 'appearing' (via singing) to be feminine. And it's all very non-ironic.
Come to think of it, male singers using falsetto is quite a usual thing in popular music (Queen, anybody?). Using falsetto in conversation is considered quite unacceptable, of course, but somehow singing makes it okay in the eyes of the patriarchy. Curiously enough, the comments page on youtube (always a hotbed of homo/queer-phobia and sexism) contains only one sexist remark, and only a few polite "that guy sounds like a girl" comments.
I suppose that this acceptance of falsetto singing ultimately stems from women not being allowed to sing in the Catholic Church years ago. That was extremely sexist (and weird), of course. But today, it's simply a pleasant exception to the patriarchal, feminine-equals-bad attitude.