I just found out about it tonight, but it reminds me of all the problems and all the benefits of Craigslist (and really connecting with other people for example). Unlike the broadcast, asynchronous mediums of YouTube, etc. , this site seems directly made so we can connect with a a real person and be entertained (in the broadest sense). The anonymity allows people to do things that they wouldn't normally do when connected to their identity (allows cool performance art too).

You'll notice that a lot of folks like to visit chartroulette together with friends because it's like going out. Being able to tell somebody... "crazy night, we saw... and...."

The internet is supposed to be our window into another world right? I guess this is the first real start of that. And... maybe, just maybe, we'll be entertained by someone like us (or shocked by a fat guy in a bra).