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#4 Ric Flair - 1992
The 1992 Royal Rumble match was the first match to have an actual prize at stake. The prize? The WWF World Heavyweight Championship. It was a star-studded Royal Rumble with names such as Roddy Piper, Shawn Michaels, The Undertaker, Hulk Hogan, and Macho Man Randy Savage just to name a few. In fact, no fewer than 15 participants would go on to be inducted into the WWE hall of fame.
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Who would go on to win this historic match? None other than the Nature Boy Ric Flair of course. Flair had recently joined the WWE (then WWF). Which was surprising at the time as someone who spent almost his whole career with NWA/WCW. Ric cemented his legend when he lasted over an hour in the match.
The Nature Boy had to survive practically the entire match as he entered as the third contestant, which he did to become the WWF World Heavyweight champion for the first time in his already illustrious career.
