#1: Mr. McMahon

We know what you're thinking: that the Montreal Screwjob is what turned lovable commentator Vince McMahon into the evil CEO Mr. McMahon. And whilst the Screwjob certainly helped, the character of an evil boss ruling over everyone had already been done before, in WCW.
Years before McMahon stepped away from the commentary desk, Eric Bischoff was riding high as the evil boss of the Georgia-based promotion, whom fans loved to hate. And much like McMahon would, Easy-E would often play favourites and wasn't opposed to getting in the ring himself, when the time was right.
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The only thing Bischoff lacked, was a definable nemesis, something McMahon would quickly gather in the form of Stone Cold Steve Austin. Whilst fans can debate about who played the evil boss better, it's cold hard fact that Bischoff did it first.