Professional wrestling has depended on bad guys since the first costumed strongman made his way into the squared circle. They're as essential to the WWE as spandex. The most dastardly and longstanding villain in WWE history, however, prefers a business suit over tights.

Though his accomplishments inside the ring have been impressive (McMahon is a former WWF and ECW champion and he won the 1999 Royal Rumble), the persona McMahon created for himself was designed for him to do his damage outside the ring. After years of selling role-model wrestlers like Hulk Hogan and "Hacksaw" Jim Duggan to adoring WWF fans, McMahon saw that the audience wanted a grittier, more cynical tone in storylines, as he watched the WWF fall behind the WCW in the pro-wrestling ratings race. McMahon decided political machinations would be just as big a part of the WWF storyline as actual matches, and that he would be the central heel in new plots.

With the 1997 "Montreal Screwjob," McMahon ushered in a new era in the history of WWF in which the announcer Vince McMahon would morph into the character "Mr. McMahon," and be as much a part of the show as he was a part of the business. McMahon remains a sinister part of the WWE storyline to this day.