Seeing Clippy on my screen is pretty funny. You could take this many steps further though and implement the Clippy animations. I always hated the one where it would raise it's eyebrows at me with this really smug look. Also, nice touch on the passive aggressive Clippy pop-up messages.
The ability to change pop-up time would be a nice addition as well. Nice job, a fun little app that's brimming with possibilities.