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.
