15 Most Boring Matches Of WWE's Attitude Era

13. "Stone Cold" Steve Austin vs. The McMahons - King Of The Ring 1999

The main event of the 1999 King of the Ring featured the highest stakes in WWE history as then-CEO of the company "Stone Cold" Steve Austin battled Vince and Shane McMahon in a Ladder match. The contest was undeniably hot, what with the most popular Superstar of all time battling the corporate villains that had helped fuel the renaissance of World Wrestling Entertainment late in the decade. But sometimes, the story behind a match is not always enough to ensure that it will survive a descent into the doldrums. That was the case with this notorious stinker, the headline bout of one of the company's worst pay-per-view offerings ever. It was essentially a cat-and-mouse game that saw Austin chasing and preventing the McMahons from climbing the ladder and retrieving the briefcase, all the while dishing out a sizable can of whoop ass to ensure fans would not grow tired of the formula. While living in that time and era, and being engaged in the story may have helped prevent total boredom, the match does not hold up, nor does the story, which descended into ridiculousness sometime around the moment Vince revealed himself as the Higher Power a few weeks earlier. The McMahons won back power of the company, essentially resetting the "rebel vs. authority figure" storyline that had dominated the previous year.