It's a tie between Jack Thaddeus and the Asperpedia Four. Jack made Chris sing Ok2bgay like a constipated Muppet, which I found to be one of Chris's more hilarious moments, and further pushed Chris's buttons with the homosexual CWCipedia ads. The Asperpedia Four took the CWCipedia shenanigans even further by posting disgusting pictures of Sonichu characters and other nasties on that site, REALLY pissing Chris off.