#2 Brian Pillman

Brian Pillman rose to fame as the face of WCW’s Light Heavyweight division in the 1990s. As age and injuries caught up to him, however, he needed to reinvent his image to stay relevant when he could no longer fly around the ring. The result was the Loose Cannon gimmick—playing crazy and constantly working not only fans but his colleagues as to whether he was playing a character or he had actually lost his mind in real life.
The character reached new heights when Pillman conspired with Eric Bischoff to get his release from WCW, and take the Loose Cannon on the road and build upon his legend across ECW and WWE. Theories and accounts vary as to whether the end game was always for Pillman to come back to WCW a bigger star and make more money, or if Pillman were playing Bischoff.
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Regardless, he was a character who consistently walked the line of making fans wonder whether he was playing a character or being his crazy self, including attacking Bobby Heenan on air, calling Kevin Sullivan “booker man” in a match, or later shooting the “Pillman Has a Gun” angle with Steve Austin on Raw.
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