WWE Royal Rumble: Ranking Every Winner After Lynch, Rollins Wins

Credit: WWE.com

35. Mr. McMahon

As much as we love to look back on the Attitude Era through rose-colored glasses, it was, in reality, a bit of a mixed bag. For proof, look no further than the 1999 Royal Rumble.

Going into the show, the dastardly Mr. McMahon had placed a bounty on Stone Cold Steve Austin’s head. Whoever eliminated the “Rattlesnake” from the Royal Rumble match would receive $100,000. With Austin entering at Number 1, it seemed certain that McMahon would prevail.

The plot thickened, however, when the Chairman failed in his attempt to win the Number 30 spot via the Corporate Rumble on Raw. This meant the McMahon would enter at Number 2, spending the early phases of the match alone with Austin.

With the story being told, an Austin victory for the third consecutive year seemed like the only logical choice. (Un)Luckily, Vince Russo has never been a believer in logic. McMahon won the match, last eliminating Austin, who was distracted by The Rock.

He would not compete at WrestleMania, however, instead losing his right to challenge in a memorable cage match with Austin at St. Valentine’s Day Massacre. As memorable as McMahon’s Royal Rumble victory was, it ultimately served no purpose other than swerving the audience. Instead, it was merely a different means of setting up the obvious Rock vs. Austin main event.