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#4 Heel Jim Ross
Arguably the greatest commentator to ever don a headset, Good ol' J.R. Jim Ross was the voice of the WWE for years, providing classic commentary to some of the biggest matches of all time. Despite having such a way with words that even the most cynical fans got hooked, the decision was made in 1996 to turn the beloved figure heel.
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After Scott Hall and Kevin Nash left the company for WCW, Ross began managing fake imitations of the characters of Razor Ramon and Kevin Nash (the latter of which was played by Kane). Insulting the fans intelligence along the way, the story didn't make any sense, as all it did was remind fans that the stars they wanted to see were now available for viewing on the competition's broadcast.
After months as the manager of the pair, Ross would simply return to his babyface play-by-play role as a commentator without any explanation, and though he would turn heel years later as the manager of 'Dr. Death' Steve Williams, this second turn didn't make any more sense for one of the most beloved men in wrestling.
