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Will Kirby, Big Brother
"Dr. Will" is unquestionably the greatest Big Brother player ever. His gameplay has the distinction of being straightforward and deceptive at the same time. Even though he was almost always Public Enemy No. 1, he somehow found a way to trick people into letting him stay — all the way to the finale. He's so slick, the exact same formula almost helped him win again during the All-Stars season. Alas, he fell on his sword and let Mike "Boogie" Malin, the other member of his Chilltown alliance, take the victory.