When songs are written in first person, they are always sung someone of the same gender as the "speaking" character. I only noticed this a few years ago when I heard a counter-example by a relatively obscure synthpop band (G.L.M. by Thou Shalt Not). At the time, it seemed like a clever, experimental thing to do, but I forgot about it fairly quickly.
Recently, my interest and pursuits in Irish Traditional Music (which have been overwhelmingly directed toward instrumental dance music) have brought me into contact with the Irish ballad community...which, in striking contrast to every musical community I've encountered thus far, seems to attach no significance to whether the gender of the song's singer matches that of its character. When I was searching for different versions of The Maid of Culmore, a romantic lament told from a male perspective*, I found it performed by a slew of both male and female performers, the most popular at present being a version by Cara Dillon. This gender ambivalence appears to be the rule rather than the exception.
In addition to making me aware that a spectrum exists of how tightly coupled singers and characters are, this really highlights how ingrained we are, as a culture, at one end of that spectrum. Katy Perry's career, I daresay, exists because when she sang that she "kissed a girl and liked it", people interpreted it as a song about lesbian experimentation. If it weren't assumed that the singer and character were the same person, this lyric wouldn't be nearly as evocative. Imagine if this song had been released by a male singer...it would be a very odd understatement of sexuality, wouldn't it? Unless, of course, the male singer was openly gay...but if, like me, you see how that would completely change the context, that only further demonstrates how closely you associate the identities of singers with characters.
This all suggests a number of questions, to which I have no answers. Why is singer-character gender matching the current standard? Why is it different in the Irish ballad community? What's the standard in other folk song communities? Has the standard changed over time, and if so when, how and why? Is the current expectation empowering or restrictive?
*I've only done cursory research into this, but based on the history of gay rights and related attitudes in Ireland, I think it's a safe bet that all traditional ballads involve straight characters.