Clippy

Clippy, formally Clippit, is the paperclip with eyebrows who interrupted a decade of Word documents to ask if you were writing a letter. Designed by Kevan Atteberry and shipped with Office 97, he was switched off by default within a few years and fully retired in 2007, at which point the mourning began. The internet ironically missed him into permanent resurrection: he is now an emoji, a meme, and a nostalgia icon. The most famous failed assistant in software history, more loved in death than he ever was at work.