Every Heel WWE Royal Rumble Winner Ranked From Worst To Best
4. Mr. McMahon (1999)
A tremendous joke extended to the exact point of expiration without ever crossing the line completely, Vince McMahon's Royal Rumble mere participation from the #2 spot was deemed terrifying enough for the boss, let alone the sh*tkicking he was due to take from Steve Austin as well.
The ill-gotten victory was so inspired, too. Interference from new WWE Champion The Rock set things in motion for the dream WrestleMania XV main event at the exact moment it was technically pitched that the Chairman was going to headline it himself.
It also satisfied another Attitude Era staple - the ends justifying the means on and off screen. McMahon got his reward for his suffering, and WWE crafted a memorable finish from one of the worst Royal Rumble matches in company history. Nobody recalls the moments wrestlers were left alone in the ring, the inelegant transparent divide between the nobodies in the first half of the match and the select stars towards the end. It's all about the conclusion, and what an epic ending it was.