When Office XP launched in about 2001 Microsoft had a comedy microsite all about Clippy being forced to retire (the angle being that XP was so easy to use he was no longer needed). It was entirely based around the idea that everyone was sick of clippy.

They had a couple of flash animations (the contemporary equivalent of a viral video), recorded here for posterity. Clippy was voiced by Gilbert Gottfried

Part 1: https://www.youtube.com/watch?v=tu_Pzuwy-JY

Part 2: https://www.youtube.com/watch?v=82KZG3Zy8xU

Part 3: https://www.youtube.com/watch?v=sAsV6_AawVw

Remains of microsite here: https://web.archive.org/web/20031009044305/http://www.micros...

There was also a downloadable blues-type song which was titled 'it looks like you're writing a letter', I can't find it anywhere now but it was pretty good

edit: found the song! its at 1:01:35 in this video: https://youtu.be/8bhjNvSSuLM?t=3690