#1.) Ric Flair – 1992
Time spent in the match: 1:00:02
It only makes sense that the greatest of all time was also the greatest Iron Man of all time in the greatest Royal Rumble of all time. 1992’s edition of the Rumble was star-studded from start to finish and the drama, the intensity, the storytelling and a frantic Bobby Heenan screaming in anxiety throughout the match truly made it one to remember.
Flair was the dirtiest player in the game and he applied his dirty tactics and weasel-like behavior to cleverly avoid elimination throughout the match. It was absolute genius and it worked, as he won the Rumble and lifted the WWE Championship (the 1992 Rumble was for the WWE Championship).
Heenan screaming with joy afterward was absolutely hilarious and there are very few things that went wrong.