#1 'Stone Cold' Steve Austin (WWE Royal Rumble 1997, 1999, and 2002)
Stone Cold Steve Austin has been the Iron Man in the Royal Rumble thrice, the same number of times he's won the 30-man match. He only won one of the matches where he was the Iron Man, though. Austin's second and third victories came from numbers 24 and 27, respectively. His first, however, came from number 5.
Austin lasted over 45 minutes in the 1997 Royal Rumble Match and eliminated a whopping 10 Superstars en route to a controversial victory. The Rattlesnake was tossed out of the match by Bret Hart but slid back in while the ringside officials weren't looking, proceeding to win it.
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Another controversial Rumble match came two years later, as Austin began proceedings with Vince McMahon. They first the first two to enter, and the final two left. As a result, both Austin and McMahon were the Royal Rumble Iron Men in 1999, even if the Chairman of WWE picked up the victory, thanks to The Rock.
Stone Cold Steve Austin put in his third Iron Man performance at the Royal Rumble in 2002. Entering at number 19, his time spent wasn't particularly long. Such was the structure of the match that. Austin lasted 27 minutes and did eliminate seven men, lasting until the final four.
With such eventful spells at the Royal Rumble - with or without the victory - Stone Cold Steve Austin is the most successful Superstar in this illustrious match's history for more reasons than one. And that's the bottom line!