Launch date: March, 1995

Fatal flaw(s): Lack of adoption

Microsoft's BOB may be one of the most popular tech fails of all time. Designed to be an easier-to-use desktop for new computer users, it wound up being more confusing than Microsoft's Windows interface. After a lack of interest, Microsoft cut the cord. But not before taking some of the characters used in the "living room" setting, like Clippy the paper clip, and throwing them into other software titles.