Something Awful is the brainchild of Richard "Lowtax" Kyanka, who remains in control of the site, despite the proliferation of writers and administrators who have assisted him over the years. The earliest comedic features of the website appeared originally on Kyanka's personal site ARCCentral, but were popularized on Planetquake including Cranky Steve's Haunted Whorehouse, which at that time presented comical negative reviews of user-made Quake II maps, and other reviews, notably of a Doom comic book, and some movies.

After he was forced to resign from Planet Quake for publishing a derogatory Cranky Steve update about a fellow employee[4], Lowtax moved his personal features to a new site, entitled Something Awful, in late 1999. During this early period, Lowtax created some of SA's most famous and long-lasting characters and catchphrases, such as Jeff K., the Space Robots ICQ prank, and the Awful Link of the Day feature.