I found myself yesterday perusing the UserFriendly.org website, which is essentially Dilbert aimed at the hardcore geek and IT crowd.
Started up in 1997 by JD 'Illiad' Frazier, it described the daily lives of workers of a small Canadian ISP mixed in with some oddball characters from the works of H.P. Lovecraft, along with the Dust Puppy, who was a collection of dust bunnies and other detritus come to life (with Hobbit-like feet!), and Erwin, a sentient artificial intelligence residing in an old SGI O2 workstation (although at times he also resided in an iMac, a iPod, and an ancient IBM PC).
The strips were published daily online, and IIRC were also published in some tech magazines in the late 1990's and early 2000's. Unfortunately, due to personal reasons, Illiad has stopped producing new strips since mid 2009, but the strips are still archived online at the site.
The casual observer who is not familiar with the ways of geeks, nerds, and IT workers in general may find the punchlines and the plots confusing, but it still offered a unique point of view of how IT and our Internet culture has evolved in the early days when the Internet and the World Wide Web was new and exciting and seemed limitless.
Also, if you can find it at Amazon, the book 'Ten Years of UserFriendly.org', a huge 1000-page tome of the first 10 years of the strip is worthy to add to your library.
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