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#4. Ric Flair – Royal Rumble 1993 and 2007
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Hundreds of superstars have entered the Royal Rumble. But hardly anyone has a career as vast as Ric Flair. NWA, WCW, WWE, and TNA have all witnessed the excellence of The Nature Boy.
He was the first entrant in the 1993 edition of the Rumble. He spent 18 minutes in the ring and eliminated Papa Shango. The 16-time world champion did the same in 2007 as well. However, he became the first superstar to get his hopes crushed.
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#3. Dolph Ziggler – 2010 and 2013
Dolph Ziggler is the only superstar to enter the Rumble at #1 and #30 multiple times. Despite employing every tactic, he's yet to win it. The Showoff started the match in 2010 but was eliminated by CM Punk.
Things were different three years later. He remained in the ring for 49 minutes and was the Iron Man of the match. Ziggler eliminated Jericho and The Godfather in his quest, which was ended by Sheamus.
