Ever since his frequent appearances on screen as a character, there have been very few superstars who the crowd have invested in as much or reacted as much for than the evil Mr McMahon. Through nearly fifteen years, McMahon made himself the most hated man in all of pro wrestling.

He did this in order to get fans to cheer for the superstars who he feuded against. If he were feuding against any superstar, you knew that there were big plans for them. He was perhaps involved the heaviest during the Attitude Era, where he was instrumental in the rise of “Stone Cold” Steve Austin and The Rock, the two biggest stars of the generation and maybe even of all time.

Through the years, he’s given us several moments of unforgettable entertainment, whether it was making us laugh, cry or hate his guts. Among all of those memorable moments, here are the ones we think are the five best.

Next Page: Vince McMahon’s 5 Greatest Moments In WWE

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