according to computerworld readers, microsoft bob is the biggest tech flop of all time.

its pretty funny when it came out i thought it was exactly what my grandma needed to help her out with using her computer. it was supposed to have a fun and pratical user interface. it had a layout like your house where there was a desk with a calendar on it if you clicked the calendar your calendar program would open if you opened the drawer there was a calculator in which it would launch calc. the type writer opened your word processor and so forth.

according to wikipedia bill gates wife (Melinda French), before she was mrs. gates, lead the project but she left microsoft shortly afterwards.

Bob included various office suite programs such as a finance application, and a funny word processor. The user interface was designed to be helpful to novice computer users, but many saw its methods of assistance as too cute and involved. Each action, such as creating a new text document, featured the step-by-step tutorials no matter how many times the user had been through the process; some users considered this to be condescending. Users were assisted by cartoon characters whose appearance was usually vaguely related to the task.