You know, I think I've actually gone the reverse of most people -- I'm just now starting to play characters older than myself.
When I first started playing, I was just barely 18... It made more sense to start a character between the 16-18 region, cause it was fresh in my memory, something I'd know how to play, and historically in keeping with the "adventuring" ages of medieval folk. On the other hand, roleplaying a character who was 19 or 20 seemed just a bit like wearing platform shoes -- adding this arbitrary bit of maturity to the character. It seemed weird, especially when I was new to the game, and looking at every little detail and wondering "could this be a faux pas?"
After the first character or two, I just started playing characters who were my own age... It seemed the most natural. Lately, though, I've noticed my characters have been getting a little bit older, as I've gotten a lot more interested in giving my characters a past, and age just makes more room for that.
Of course, I still vary all over the map. Sturm in Living ENWorld is barely out of high school, so to speak... As a dwarf, it's hard to perform a direct conversion, but that's where his attitude and history are. Other characters are a bit older, especially when I play a game that starts at higher levels (I almost always use that as an opportunity to play the "grizzled veteran", heh.) In general, when I start a character these days, it's in the middle-20s to early-30s range -- maybe it has something to do with a graduate school mentality, where life doesn't begin until you have a Master's degree (in other words, until you run out of ways to postpone it.) Dunno.
Good thread though. One of those things I'd've never thought to look at.