I think designing the Microsoft Agents (clippy, merlin, bonsi buddy...) has been the most challenging endeavor in that it's really hard to make something friendly and helpful without being incredibly obnoxious. I see why Clippy got so much hate after all these years.
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Just make him condescending and rude ๐
I have an idea! Remove Clippy, and instead make a weird shape that looks like perfectly bent wax paper with a gradient on it, and put it in EVERY app, not just the office ones! Give it a robot mind, too, so that it'll know how to stop you from accessing sites that aren't "Microsoft Internet Explorer"