When Microsoft retired Clippy (homeip.net)
Clippy was the unofficial nickname of the office assistant, a feature present in Microsoft Office 97 and Microsoft Office 2000. His proper name was Clippit, but nobody I knew called him that. Clippit, or Clippy, was inspired by Microsoft Bob, a misguided attempt to make Microsoft Office friendlier, more helpful, and easier to use. But most frequently, it was more annoying than any of those other things.