Microsoft Bob: An operating system overlay that lives in infamy.

Microsoft Bob was Microsoft’s ill-fated attempt to make computers easier to use. Debuting in 1995, Bob quickly became the most hated-program in Microsoft history.

It failed miserably.

You would be hard pressed to find many references to it on the Web, especially on Microsoft’s own site. Strangely enough, it had a lot of the annoying pop-up functionality that was integrated into Microsoft Office with Clippy, and Vista with its constant requests for verification of actions.

Some people never learn.

To see some screen shots of Bob go to the gallery at Tech Republic