Scott publishes his first self-written humorous content to the site, a series of top ten lists lampooning the Star Trek shows he enjoys. The idea is inspired by another site, but Scott tries to top it by imitating Letterman's humor and internal jokes like a reference to Klingon coffee in each list. To this date, his lists can still be found on other sites that stole them. Scott finds he likes creating his own humorous content much more than stealing everyone else's and begins a years-long campaign to create silly pages that mostly entertain himself.
One of Scott's favorite activities with friends is hosting murder mystery parties, based on either boxed sets bought at the store or self-written. They allow people who would never touch a role-playing game to enjoy one without realizing it, and they provide for even more silly photos of his friends for his site. Matthew Preston, Jason Fedorow, Kelly Lee, and other friends appear in his sets from 1997, and two years later Denise Sawicki and Lori Lancaster show up in a later edition.
After a budding RPG campaign with Matthew Preston falls apart due to Matthew moving away, Scott decides to take it online, and invites Jason Fedorow, Erik Nelson, and other friends to play. This fantasy-themed text game, written in daily installments by Scott with nightly email input from the players as to what their characters will do next, becomes The Island at the End of the World and eventually spans almost five years and five thousand pages of text, easily dwarfing all other content that would ever grace Scott's site. It keeps Scott interested in the web for years and its successors still survive today.
Always interested in showcasing his friends on his site, Scott takes advantage of the "web ring" trend for linking sites together. He creates one for his circle of high school buddies, who call themselves the Rat Pack, including Lori Velàzquez and Andy Hubbartt. Friends of those friends are also allowed to put their sites in the ring, including Jason Fedorow and Erik Nelson. It doesn't help any of them gain traffic, but it the photo of Jason wearing a tin foil helmet becomes an iconic image for their sites.
Always one to jump on a bandwagon and mock it from within, Scott writes a humorous mission statement for his site, defining its core principles. Among the site's less-absurd goals: "To use paintbrush programs to alter photographs of people so that they won't like me any more," "To make the people who designed HTML code wish they'd never been born," and "To give my friends ideas to steal, and to steal my friends' ideas." Mission accomplished.
When Scott isn't typing HTML in a dark room like a hermit, he enjoys going with friends to the local park and soaking each other silly with squirt guns. To celebrate their shared birthday in high school, Scott and Jason Fedorow inaugurated "BloodHunt," a semi-annual party in the forest preserve with Super Soakers and as many friends as they could talk into attending. Photos from the 1997 and 1998 sessions make it to the site and provide fodder for doctored photos for years to come.
The site's first true interactive section open to the public, since the Island game was separate and only open to Scott's friends, is a silly page in which Scott poses as gypsy fortune-teller Madame Udfar (anagram for "fraud") and answers advice queries submitted by friends, mostly Jason Fedorow and Lori Velàzquez. It isn't published on a regular schedule, but it is the first time Scott invites anyone reading to submit content, which would later become a pillar of the site. Another recurring content feature at this time is CuongWatch, in which Scott posts breathless updates on the health of Jason's friend Cuong, including such alarming injuries as mild sunburn and "aches."
When he designs the third version of his site, Scott creates a lower frame across the bottom just to promote his friends' sites with banner ads of his own design. it's another low-tech, high-silly way to link to them and keep his friends involved in his site. Such folks as Matthew Preston, Lori Velàzquez, Jason Fedorow, Erik Nelson, Andy Hubbartt, and Kelly Lee get the treatment. Andy Hubbartt is unhappy with his high-school nickname appearing on his image and asks Scott to cross it out, becoming the first time Scott has to remove personal information at a friend's request.
Scott continues creating self-contained humor pieces for his site, mocking such interests as ER and his Nintendo 64 as well as his experiences on the job at Taco Bell. Among the most absurd pieces from this era is Stupid Kids Gallery, a series of scans from his childhood psychology textbook with silly captions, still one of the conceptually oddest pieces to show up over the years. Scott soon gives up on his Education major (switching to English) before he can create any sequels.
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