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Rollin' and Trollin' is a video of downtown CWCville (really downtown Charlottesville) uploaded on 17 July 2009 in which Chris attempts Kaufmanesque humor. Notable is a video message to real life trolls, including several CWCki editors. The key component of this message is that, in a shocking turn of events, Chris was engaging in the most elaborate trolling scheme in history, and has duped us all masterfully. (If only that were true.)

To sell the deception, Chris changed his look to have a normal hairstyle, a goatee, sunglasses instead of large, square pedo glasses, plain blue T-shirt and jeans, navy blue sleeveless unbuttoned shirt over his t-shirt, dog-collar bracelets, his forearms appear to be covered in thick tattoos, complements the tattoo sleeve from the fuck quest, no Amnyfest Ring, and a chain with some dog tags, instead of his trademark Sonichu medallion. Of course, the disguise unintentionally gave away the truth: the lack of the ring and medallion suggested that Chris was not entirely TRUE and HONEST when he made this video, something that he indeed confirmed later.

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