To me, Clippy represents designers' obsession with a cloyingly sweet First-Time User Experience that makes the product unusable if you actually retain the user.

To me, Clippy represents designers' obsession with a cloyingly sweet First-Time User Experience that makes the product unusable if you actually retain the user. I think he lives on in "let's make the settings menu a text conversation with a chat bot!," unskippable cut scenes in games, and other overly cute ideas.