An operating system made by Microsoft in 1995. Instead of a "desktop," it used a "room," where all your programs were objects lying around the room. It also had little talking characters (including a dog named Rover) which tried to give helpful advice but were usually just annoying. If you've never heard of it before, do a search on it or something.
Have you ever used Microsoft Bob? That talking dog is so f*cking annoying!
Bob has to be one of the worst Operating Systems ever. Actually, I don't think it is an OS. But, it's so terrible, you just got to laugh at it. On top of that, Microsoft fails to recognize this as one of their own products!
1: Did Vista get crappier?
2: No, it's Microsoft Bob.