#2. CM Punk – Royal Rumble 2011 and 2014
The 2011 Royal Rumble was bigger than usual. 40 men entered the event, and CM Punk was the first. He survived 35 minutes and eliminated seven superstars. Accompanied by Nexus, Punk looked pretty strong to win the Rumble until getting eliminated by John Cena.
The Best in the World entered the event three years later at the same spot. This was the last time he was seen in WWE. He started the match against his former protege Seth Rollins. His hopes were slain when an already eliminated Kane showed up to remove Punk from the equation.
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#1. The Miz – 2012 and 2015
The Miz is the most recent superstar to enter the Rumble at #1 twice. Luck favored him as he survived for 45 minutes in 2012. However, his tactics didn't protect him from The Big Show.
He repeated the entry spot three years later. However, he failed to replicate his earlier performance and was eliminated by Bubba Ray Dudley within four minutes.