Microsoft Clippy (1997-2001)
Microsoft shipped Clippy, an animated paperclip, in Office 97. It popped up to "help" users write letters and format documents and became one of the most mocked features in software history. Users widely described it as intrusive and useless.
Clippy was disabled by default in Office XP in 2001 and quietly retired from later versions.
Clippy became shorthand for AI assistants that get in the way, making Microsoft cautious about assistants ever since.
Copilot is Microsoft's third attempt (after Clippy and Cortana) to embed an assistant in its productivity suite. The underlying AI is real this time, but Clippy's lesson stands: users abandon assistants that add friction rather than value.
