If you think Vista was Microsoft’s worst product ever, you’ve never seen Microsoft Bob. Bob was Microsoft’s attempt to make computers easier to use in the 90s. Here’s a look back.


Microsoft gets a lot of abuse about Windows Vista. You’d think that Vista was the worst thing Microsoft ever created. In fact, Microsoft Bob was a much worse train wreck.

Microsoft released Bob in March 1995. It ran on both Windows 3.1 and Windows 95. Bob was an attempt by Microsoft to make Windows easier to use. The idea was that rather than confusing icons, folders, and random desktop icons, users would have a more “intuitive” desktop layout that resembled  a room in their house. Rather than cold icons, users could create custom things like chairs and computers that would refer to programs they used. Objects could be moved freely around the rooms so users could feel more at home.

To help make navigating the computer easier, Bob included “Personal Guides” who were known as Friends Of Bob. Think Clippy for your entire operating system. In reality, Personal Guides were the forerunners of Clippy and his ilk and performed the exact same function. Clippy was introduced with Office 97, but some Bob Personal Guides survived intact in other incarnations for a while. The main Personal Guide, Rover, lived on as a Search Assistant in Windows XP. The Dot survived through to Office 2003 as an Office Assistant.

Even though Microsoft Bob features lived on for a while, fortunately Bob itself died a quick and merciful death. Even though Vista might not have turned out the way many of us might have hoped, think how bad it could have been if Bob had survived as the main operating system interface!

Check out the Microsoft Bob Dinosaur Sighting Photo Gallery. You can take a look at Microsoft Bob and see exactly what it was like.