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I. Early Days

1999 was a bad time to be in the website business. The dot-com bust was hurtling toward the internet with the speed and certitude of the Chicxulub asteroid. Five trillion dollars were about to evaporate, caught in a constellation of collapsing venture capital-backed stars like Pets.com—Amazon if Amazon only sold cat food—and Broadcast.com, which was just radio on the internet. It was, therefore, a good time to be a cynic. "The internet makes you stupid" has been the motto of SomethingAwful.com since Richard Kyanka, 40, registered the domain in 1999.

At first, Something Awful was what we would think of as a blog, though that term wouldn't enter common parlance for a while, yet. It was a goulash of parodies of Silicon Valley groupthink and internet dumpster diving. What set Kyanka's site apart was its cynicism—about everything, but particularly about the role the internet would play in a changing society. He was, from the start, a prophet of doom.

Kyanka's dark, esoteric humor proved popular among a certain set—typically young, typically male, often though not always left-leaning. Experienced travelers in the internet's darker corners. It was the best of its day: independent, original, and fiercely creative. It was also the worst: insular, exclusionary and, at times, vicious.

This is the story of Something Awful, as told by the people who made it what it was.