#5 Vince McMahon breaks kayfabe and kick starts the Attitude Era.
Most of the time, kayfabe breaking moments happen completely by accident. Someone gets a little worked up, like with Brian Pillman in our previous slide, or forgets their lines, like Sid Vicious. However, there was one major instance where kayfabe was shattered by none other than Vince McMahon himself--and it was entirely on purpose.
For years, WWE had been steadily losing ground, with fans abandoning the promotion for WCW, mostly because former WWE talent like Hulk Hogan and Macho Man Randy Savage were under contract there. Realizing they had to do something new and different, Vince decided to start catering to the males 18-34 year old demographic.
As part of the new initiative, he came on WWE television and delivered a promo basically stating that WWE was going to try new, more complicated storylines and characters. "We feel that wrestling fans are tired of having their intelligence insulted with 'good guy vs. bad guy."
Not only did Vince smash Kayfabe into oblivion, but he also unofficially started the Attitude Era.