#1.) 1992
Winner: Ric Flair
There’s simply no Rumble match greater than 1992. Apart from the fact that it was the most star-studded Rumble in history, the drama and build and execution were all done to absolute perfection. Ric Flair was the Iron Man of the match, becoming the first competitor to ever last an hour in the Rumble.
He entered at #3, and being the dirtiest player in the game, found all sorts of tactics to win the match. Eventually, he outlasted many of the all-time greats and ended up winning the Rumble. The crowd was hot and it was Bobby Heenan‘s finest hour as a commentator. His frantic screaming and paranoia throughout the match and eventual scream of joy was an absolute marvel to watch even all these decades later.