Here is my experience with ChatRoulette:
Some people seem to be creeped out by it and some of my friends think it's something to do when you're bored with a group of people. I came across it last spring and was a little addicted to it for awhile. It can be very entertaining- one time, two of my friends convinced a bunch of teenage girls they were the band MGMT and living up to their rockstar image, sort of promoted a drug culture until the girls mother walked in and then they signed off haha. I have met a bunch of people from different countries and have even formed some friendships. I now have a friend from Chile (we're Facebook friends so it's official) and have skyped with some people. My Chilean friend helps me with my Spanish so that's pretty cool. Even though ChatRoulette can be a bit sketchy, I think it's kinda awesome.