A big fat thank-you goes out to Toybox for pointing out something that I really should have known about earlier: OS-tan. Originating from 2chan.net aka Futabachan, this is one of those odd could-only-happen-on-the-internet things that would probably have gotten a lot of press if it had happened in 1999. Basically a bunch of Japanese folks made some charicatures of a variety of operating systems, represented by little cartoon girls. Windows 95 fights a lot with the Macintosh OS girls, Windows ME is unreliable and flakey, et cetera.
I have some catching up to do here, as there appears to be a rather large amount of material out there, including a number of yon-koma comic strips (samples are available on the Toybox page, as are a number of handy links). Looks hilarious. I look forward to putting one of the Windows CE drawings onto the desktop of my PDA.
*Edit on 2005-01-04: There is a rather extensive Wikipedia entry regarding OS-Tan now.
http://www.os-tan.com/
OS-Tan Image Archive. Thousands of colour and original black and white images of the OS-Tan girls.