Nobody can deny that Triple H hasn't always played by the rules, and throughout his career, The Cerebral Assassin has found ways to continuously torture one man -- Mr. McMahon. One night in November 1999, however, The Game took his disdain for the Chairman down a shocking different aisle when he disrupted the nuptials between Stephanie McMahon & Test in WWE.com's No. 9 Greatest Moment in Raw History.

As the Billion Dollar Princess and the groom-to-be prepared to exchange their vows, Triple H played the part of wedding crasher. An incensed McMahon family could only stand in awe and watch as The Game produced video footage of a drive-thru wedding ceremony in Las Vegas. When all was said and done, Triple H had done the unthinkable and married the apparently drugged daughter of the Chairman, spoiling the biggest wedding in WWE history.

Adding to the shock of Triple H's despicable actions, weeks later at Armageddon, The Game went one-on-one with the Chairman in a Street Fight, with Stephanie seemingly supporting her father at ringside. "Daddy's little girl" turned her back on her father and showed the world that her marriage to The Game was truly a match made in hell -- for the Chairman. The Game and Stephanie ushered in the McMahon-Helmsley Era, but its seeds were planted on Raw.