What is Microsoft Bob?

Microsoft Bob was a software product developed by Microsoft for Windows 3.1 and Windows 95. It was an ambitious project, aiming to give non-technical computer users a dynamic environment to do all sorts of things with their computer. It featured a number of suite programs, 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 computer writers and pundits. Virtually everyone who wrote about technology in any capacity at some point made fun of Microsoft Bob, and it became one of the early touchstones of Internet humor.

Microsoft Bob was basically an environment meant to replace the Program Manager. It replaced it with a cartoon environment, chock-full of tutorials and cute anecdotes, and surrounding a collection of programs used for everyday tasks.

The program started with the user approaching a front door, and being asked to identify themselves. This was done by clicking on a large door knocker. The user is then taken to the Family Room, full of various graphics, some of which trigger programs. Many of the objects, when clicked, would simply tell you, “Note: This is a decorative object. It does not start any programs or do anything special.” Microsoft Bob featured various guides, most notably Rover the dog, who would later be used in Microsoft XP as the companion for the Search feature.

Everything in Microsoft Bob featured lengthy stories and introductions, all a bit cutesy and many considered to be fairly condescending. Rover, for example, introduces himself by saying, “My name is Rover, I come from Redmond, WA, I like to eat table scraps, and, when I’m not here in the Home, I like to spend time in backyard. I’m just one of a scrumptious gang of Personal Guides here to help you find your way in the Home. Give us all a try if you want, or stick with me. The choice is yours!”

Bad grammar, numerous puns, and lengthy chunks of extraneous information filled Microsoft Bob, and made it virtually unusable for most users. Lengthy tutorials also accompanied the launching of many features, and these tutorials would spring up every time the user would launch 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 of the rooms had objects that could be moved around as 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 to still display crisply.

Ultimately, Microsoft Bob was too complex and convoluted for most novice users, and too condescending and cute for intermediate or advanced users. In spite of its age, it continues to be lampooned in the technology media, and its lasting legacy is undoubtedly one of scorn. It was named Worst Product of the Decade by CNET.com, and ranked 7th on the 25 Worst Products of All Time by PC World Magazine.

Microsoft recycled many of the characters and some of the concepts of Microsoft Bob for later Windows assistants. In addition to Rover, the assistants Dot and Will made their way to later Windows computers as assistants in the Microsoft Office Suite. Microsoft Bob himself is used as the likeness for a nerd smiley in Windows Live Messenger. Microsoft’s Greetings Workshop features a dog similar to Rover, named Rocky. And a number of Rover’s mannerisms have been replicated in the Office assistant Rex.