3. Hapless help
flickr/Shayne Kaye
No company has mastered the art of befuddling its users while treating them like idiots quite the way Microsoft has. From the "Are you sure (Y/N)?" confirmation messages in early versions of MS-DOS to the User Account Controls in Vista, Microsoft products managed to be both confusing and condescending at the same time. But nothing embodied this attitude more than Clippy, the anthropomorphic paper clip "Office Assistant" that debuted with Office 1997. Clippy quickly became a target for parody -- even Microsoft made fun of it -- as well as a symbol of everything that was wrong with the company's approach to software. By the time Office 2007 appeared, Clippy had gotten clipped.
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