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The one that I'm surprised didn't get mentioned there was Chris Jericho's transformation from "Y2J" to "The Best in the World At What He Does" Jericho. That was a huge gamble, as Jericho sacrificed so many things about his character in order to evolve, and I feel that it was the year that "made" him, if it were.
That being said, obviously greater transformations were the ones that led to the most cash being made. Hulk Hogan turning heel and going "Hollywood," The Ringmaster going Stone Cold, Hunter Hearst Helmsey abbreviating and Rocky Maivia talking in the third person all come to mind.
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