Chatroulette is a webcam-based chat service that has the unique approach of pairing users with random strangers. It’s supposed to be like playing Russian roulette, only instead of dueling with a gun, you parry verbally via typed messages and/or webcam, and if you say or do something your partner doesn’t like, they leave the chat (“kill” the conversation).
It was created in 2009 by a 17-year-old kid who ran the site out of his bedroom in his parents’ home. Even without advertising, this site grew to an enormous size by word of mouth. After several years of trial and error, it has finally reached the point where it can effectively filter out inappropriate behavior.
Users have to register and agree to the terms of service and violators will be filtered by the site’s moderators. The majority of users are under 30, and there are more male than female users. It’s definitely R rated, at least.