The Story of Clippy; The Much Maligned Microsoft Office Mascot
Microsoft seems to have some kind of fascination with automated assistants:

Most folks think that Microsoft Office’s Clippy, Microsoft Bob, and Windows XP’s Search Assistant dog were perverse jokes — but a dozen years’ worth of patent filings shows that Microsoft took the concept of animated software ‘helpers’ really, really seriously, even long after everyone else realized it was a bad idea. And the drawings those patents contain are weirdly fascinating.
Technologizer has assembled an online slide show detailing decades of patents from Microsoft showing various assistant concepts.

15 pages??
Well, Slides actually!