I personally have not tried ChatRoulette, but have heard a lot about it. (Some good, some bad)
The good usually involves people thinking of creative ways to entertain whomever is on the other end. Some people write songs about the people on the other side.
Some people draw.
Ben Folds has used it in a concert.
Pretty sweet stuff. Amazing the creativity that is out there. Still unsure if I want to dive into the world of ChatRoulette.
Although I hear it has gotten a lot better lately... more worthwhile content, and less..."junk"