What’s Microsoft Bob?

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Microsoft Bob was a failed software product developed by Microsoft for non-technical computer users. It featured a cartoonish environment with cute tutorials and anecdotes, but was too complex and condescending. Its legacy is one of scorn, but some of its characters and concepts were recycled for later Windows assistants.

Microsoft Bob was a software product developed by Microsoft for Windows 3.1 and Windows 95. It was an ambitious project, which aimed to provide non-technical computer users with a dynamic environment to do all sorts of things with their computer. It featured a number of programs from the suite, such as a word processor and a personal finance package.

Microsoft Bob was ultimately a highly visible failure. It was also, because of its campy aesthetic and somewhat condescending concept, the perfect target for writers and computer geeks. Virtually everyone who wrote about technology in any capacity made fun of Microsoft Bob, and he became one of the first staples of Internet humor.

Microsoft Bob was basically an environment intended to replace the Program Manager. He replaced it with a cartoonish environment, crammed with cute tutorials and anecdotes, and surrounded by a collection of programs used for everyday tasks.

The program began with the user approaching a front door and being asked to identify themselves. This was done by clicking on a large clapper. The user is then taken to the Family Room, filled with various graphics, some of which activate programs. Many of the items, if clicked on, would simply tell you, “Note: This is a decorative item. It doesn’t launch any programs or do anything special.” Microsoft Bob featured various guides, most notably Rover the dog, which would later be used in Microsoft XP as a companion to the search function.

Everything about Microsoft Bob featured long stories and introductions, all a bit cute and many considered quite condescending. Rover, for example, introduces himself by saying: “My name is Rover, I’m from Redmond, WA, I like to eat leftovers from the table and, when I’m not here at home, I like to spend time in the garden. I am just one of a delightful band of Personal Guides here to help you find your way into the House. Try it all, if you want, or stay with me. The choice is yours!”

Bad grammar, numerous puns, and long blocks of extraneous information cluttered up Microsoft Bob and rendered it virtually unusable for most users. Lengthy tutorials also accompanied the launch of many features, and these tutorials came out every time the user started the program and could not be turned off.
Microsoft Bob’s environment was also somewhat customizable. The program was filled with sounds, many of which could be changed, and some rooms had objects that could be moved around however the user wished. Microsoft Bob was somewhat innovative in its use of vector graphics, allowing objects to be expanded or shrunk by the user to almost any size and still display sharply.
Ultimately, Microsoft Bob was too complex and convoluted for most novice users, and too condescending and cute for intermediate or advanced users. Despite her age, she continues to be teased in the tech media, and her lasting legacy is undoubtedly one of scorn. It was named Worst Product of the Decade by CNET.com and ranked 7th among PC World Magazine’s 7 Worst Products of All Time.
Microsoft recycled many of the characters and some of the concepts from Microsoft Bob for later Windows assistants. In addition to Rover, assistants Dot and Will made their way into later Windows computers as assistants in the Microsoft Office Suite. Microsoft Bob himself is used as a likeness for a nerdy smiley in Windows Live Messenger. Microsoft’s Greetings Workshop features a Rover-like dog named Rocky. And a number of Rover’s mannerisms have been replicated in Office assistant Rex.




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