The year 1995 was a heady time for Microsoft. Windows was such a dominant platform that the company had earned the moniker “The Beast From Redmond.” It was being used on platforms everywhere. Microsoft Word was in the process of dismantling its old rival, WordPerfect, by being offered for free with Windows. Explorer was released this year, and was on its way to dethroning Netscape (especially when it was available on Windows for free some time later). Bill Gates was declared the Anti-Christ… a rep that somehow resurfaced in the year 2020.

There was another frontier Microsoft needed to conquer: average people who had no idea what all these tiny icons on the screen were supposed to do. Or how to manage a directory tree. How do you computer? The average American home didn’t have a PC in 1995, and projections that 50% of homes would have a computer by 1997 seemed speculative.

Enter: Microsoft Bob.

The marketing manager for Microsoft Bob was none other than Melinda Gates. It’s development was based on research from Stanford University. Said those researchers:

We said that people are good at having social relations — talking with each other and interpreting cues such as facial expressions. They are also good at dealing with a natural environment such as the movement of objects and people in rooms, so if an interface can interact with the user to take advantage of these human talents, then you might not need a manual.

The entire graphic user interface has now been arrange into a house, with clickable areas to get stuff done. Meanwhile, a proto-Clippy is working full force. It was like some mad Flash interface… about a decade before every internet prognosticator was telling us that Flash interfaces were the way of the future.

From Wikipedia:

Microsoft Bob presented screens showing a “house”, with “rooms” that the user could go to containing familiar objects corresponding to computer applications—for instance, a desk with pen and paper, a checkbook, and other items.

It lasted about a year and became a punching bag for Microsoft long before Bing and Zune. Here’s the number one problem: it kinda turns your computer into a giant “Where’s Waldo?”

The Wiki on the reception is among the snarkiest:

Bob received the 7th place in PC World magazine’s list of the 25 worst tech products of all time,^[13] number one worst product of the decade by CNET.com,^[14] and a spot in a list of the 50 worst inventions published by Time magazine, who called Bob “overly cutesy” and an “operating system designed around Clippy“.^[15]Microsoft’s Steve Ballmer mentioned Bob as an example of a situation in which “we decided that we have not succeeded and let’s stop [now]”.^[16]