Clippy's popups were useless, but his chat interface actually worked fine (within the domian of MS office questions) things like "how do I add page numbers" or "count the paragraphs in my document")

The pre-clippy natural language help in MS word worked fine too. Chatbot interfaces that work fine are nothing new, it's just very few programs are complex and open-ended enough for them to be a reasonable UI -- but a full-featured word processor probably is