It would take a monumental effort to book a worse Royal Rumble winner than Roman Reigns or Batista but the 1999 edition of the show managed to pull it off. That's right, the WWF decided to let Vince McMahon win the Rumble. It the midst of the Attitude Era and the legendary Austin-McMahon feud, the Royal Rumble looked to be another chapter in their story. When Vince used his power to make Steve Austin #1 in the match, commissioner Shawn Michaels countered by making Vince McMahon #2. Austin should have wiped the floor with McMahon, the non-wrestler, and faced his wrath later especially since McMahon offered $100,000 to whoever eliminated Stone Cold. What happened instead was far, far worse than anyone could have imagined. Instead, Austin tossed McMahon through the middle ropes and chased him through the crowd and into an arena bathroom where McMahon's Corporation stable beat him down and sent him to the hospital. McMahon remained out of the Rumble the entire time as well, even doing commentary while the other competitors were wrestling. In any other year, two guys leaving for this length of time would result in their elimination but this is Vince Russo we are talking about. You see, Russo wants McMahon in the match until the very end but it's not believable for him to last the entire hour. So, instead of scraping that idea because it's freaking stupid, he rewrites the rules of the match to let it happen without McMahon wrestling. The Rumble then became a parade of jobbers until around #15 but really everyone was just waiting for the inevitable Austin return. Even Kane, who was not old and useless at the time, eliminated himself because mental hospital workers chased him out of the ring. Yes, that was a thing that actually happened. Finally, the camera cut to the back to see Austin returning to the arena after hijacking an ambulance and charging the ring. Austin cleared the ring and left a final four of himself, McMahon, Big Bossman, and D-Lo Brown. Seriously, the Bossman and D-Lo? Did anyone think they would have a chance? After Bossman and Brown's easy eliminations, Austin dragged McMahon from his commentary position back into the ring. At that moment, the Rock appeared and yelled at Austin from the ramp. Like an idiot, Austin started yelling back, allowing Vince to dump the distracted Stone Cold and win the absolute worst Rumble of all-time.
