As the Internet has grown in size and popularity, the Internet medium has changed from an educational and technical content to a social and entertainment content. The Lycos search service estimates that the number of WWW pages has grown from 5 million to 6.89 million pages during the months of April to June of 1995, and will reach 10 million pages by 1996. A large number of these pages are devoted to personal pages, whereas only a few years ago personal pages were nonexistent. Similarly, the EFnet Internet Relay Chat (IRC) servers have grown from supporting several hundred concurrent users in 1991 to over 20,000 concurrent users in 1996. Both the WWW and IRC are becoming active vehicles of socialization and entertainment. This paper focuses on the technical and social aspects of a set of games designed by the authors that run on IRC, and how AI techniques can augmenthese games. In particular, we examine the game Risky Business, an online trivia game hosted by a computer program or "bot," short for robot. In addition to providing entertainment, the computer game show host also supports a unique setting that real-life game show hosts never encounter: the opportunity to interact in real-time with thousands of players, 24 hours a day, and become a cornerstone of their social interaction in cyberspace.