"It looks like you're writing a letter. Would you like help?" No question drew more ire from Microsoft Office users than Clippy's snappy opener. The assumption-prone office assistant made its debut in Microsoft Office 97 as an acrobatic virtual paper clip ready to help complete any task. The only problem was that Clippy had trouble holding its tongue. As soon as the word Dear hit the page, it burst into letter-writing mode, ready to help structure a person's most private thoughts. Clippy no longer stars in a lead role for the word-processing program, mainly because of its obsession with bouncing on users' documents and the fact that, well, nobody seems to write letters anymore.

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