One of the last single-joke humor pages that Scott creates is also one of his strangest: An Essay Exploring the Theme of Man vs. Insanity in Stanley Kubrick's The Shining, which consists of numerous paragraphs, lists, and links saying only, "All work and no play makes Scott a dull boy." Scott has just seen the movie for the first time and is tempted to create a genuine tribute page to it, but the one-joke approach seems best. It signals the end of the one-off humorous pages that for years have been a staple of the site.
One of the more complicated games on the site returns with Web Page Survivor 2: Outback Steakhouse, a parody of the second season of the popular reality show. This time, the Kooshball and Ogrecode (later Borrow Money) tribes compete in actual challenges invented by Scott, such as naming as many flavors of ice cream as they can and divvying up tasks in an imaginary household. When the contest comes down to five women in the end, Anna Gregoline's strategy to oust the popular Lori Lancaster backfires against her, and finally Lori defeats Kelly Lee to win a gift certificate for Outback Steakhouse.
After a round of the goo game in which Scott chooses celebrities representative of each of the players, he begins a special round (XIV) in which the goos are specifically requested by the players. The round opens with Yul Brynner, requested by Kelly Lee so the round could have a "king" goo (Brynner starred as the King of Siam in The King and I), and thus Brynner becomes the first player-requested goo in the history of the game. The round is a success among players and Dan Donovan suggests making goo requests a regular part of the game from then on.
The third edition of Web Page Survivor, called Stranded in the Suburbs, keeps the challenge-based gameplay of the second game but adds a new twist: The sixteen players have fictional counterparts in computer game The Sims and are stranded in swimwear on a grassy lot in the virtual neighborhood, forced to fend for themselves with minimal in-game supplies. Scott has trouble keeping up with the simulation and stops posting screenshots to the site, but the actual WPS game proceeds uninhibited. A scandal erupts near the end when Anna Gregoline, who has brought her friend Kris Weberg into the game to fill out the cast, conspires with him first to vote out their ally Kelly Lee and then to engineer the vote so that Scott will be forced to have a three-way finish with them and fellow friend D. R. Scott is furious at his game being abused, especially when Kelly suggests that he deserves it for taking it so seriously, and his outraged rant on Tragic Comedy nearly kills the game. In the end, perceived innocent D. R. outlasts his controversial opponents to win the game; Anna and Kris tie for second place.
It begins as simply as Scott aping another web fad: Calling it Tragic Comedy, he installs weblog software called Greymatter on his site and promises to keep an online journal of his daily experiences, mostly tales about personally exterminating the field mice infesting the house he rents with Kelly Lee. He opens up authorship to anyone who requests it, and soon not just Kelly but friends Anna Gregoline, Derek Sutcliffe, and Kelly's friend Jackie Mason (then using her maiden name) join the mix. The comments following each entry become so popular that the journal quickly evolves into more of a forum than a group weblog, even though Greymatter continues serving the site for exactly one year.
Five years and 510 posts after it began, Scott cancels his beloved RPG Blood on the World's Hands, an emotionally devastating decision for him. The game has been on hiatus for several months and Scott finds it increasingly difficult to get back into writing a new post every few days, and by this time most of the key players have departed anyway. With a massive good-bye letter that explains his reasons and what details would have made up the rest of the game's story, Scott ends the game thanking those who helped it grow into such a voluminous success. Two years later, he transfers his still-lingering yearnings for his old fantasy RPG into a new text-based game set in the Victorian era.
Living with Kelly Lee and having numerous gaming friends in close vicinity leads Scott to run an in-person RPG again for the first time in years. He chooses The Matrix as his theme and sets the action in a crew similar to Morpheus's team from the movie. Within a few months, in becomes clear that a web presence is needed to keep track of the rules and characters, and Scott creates a simple, stylish minisite for the game on his site. Among the players in the year-long game are Jackie Mason, trying an RPG for the first time, and Bill Valentin, who also runs a Victorian-era D&D game that piques Scott's interest.
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