1. Vince McMahon
It's not everyday that you come across a businessman quite as willing to get his hands dirty as Vince McMahon clearly is. He's the owner and CEO of WWE, but he's also had quite a few in-ring encounters over the years. We've seen him take on the likes of Shawn Michaels and Hulk Hogan even his own son but perhaps his greatest in-ring victory came at the 1999 Royal Rumble. McMahon's nemesis Stone Cold Steve Austin had won the Rumble in 1997 and 1998, and the boss was determined not to allow the Texas Rattlesnake to three-peat. In the end, Austin was given the No. 1 spot in the match, and McMahon would follow at No. 2. This meant that the bitter enemies would start the bout, and soon Austin was stomping a mudhole on McMahon. McMahon eventually managed to escape under the bottom rope, but Austin was in hot pursuit. A rather bizarre sequence of events would follow, including a beatdown in the arena toilets for Austin and a brief spell on commentary for McMahon. As it turned out, they'd be the last two men in the Rumble but McMahon was able to take advantage of a distracted Austin and come out victorious. It was a major chapter in the Austin vs. McMahon rivalry, and the setup to the first of three excellent WrestleMania matches between Austin and The Rock but the idea of Vince McMahon winning the Royal Rumble remains as strange today as it was back in 1999.