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Zeeboe missed the point of Muhammad Hassan completely. That character was too deep for wrestling. He probably would have been considered less offensive if he were an actual terrorist.
Triple H and JBL have been mentioned, but I'm not sure if I disliked their characters or just because they fucking bored the shit out of me during that period. Eddie Guerrero did such a great job as a heel in his program with Rey Mysterio just before his death that I marveled, but at the same time I just couldn't stand the guy. He wasn't a "cool heel," he was a detestable broken piece of crap heel. Whereas Chris Jericho was always a little fun to root for when he went "darker" and dropped the Y2J shtick in 2008.
I find Zeb Colter absolutely hilarious and I love him, but the stuff he does as a heel is fucking ballsy shit.
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