At 1999's St. Valentine's Day Massacre pay-per-view, Stone Cold took on Vince in the show's main event, a Steel Cage Match no less. Now, nobody went in expecting this to be a great wrestling bout and many even thought it was rampantly egotistical of McMahon to shove himself in the main event of his own promotion's show, something they'd be right about. That said, McMahon threw down the gauntlet to his doubters mid-way through the match by taking an extremely impressive bump off the top of the cage. Austin rams his head into the cage, sending McMahon flying backwards through a table. It showed just how ballsy McMahon was (the grapefruits!), and that he wasn't asking his employees to do anything he wouldn't himself. Plus, it looked genuinely scary on TV, like Vince may've been legitimately injured, all the more so because the backwards bump didn't give him much opportunity to check his landing. You've gotta give him some credit for this one, and it's a classic WWE moment.
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