#1: Shawn Michaels(1995)
Kicking off this monstrous Royal Rumble match is none other than the Heartbreak Kid Shawn Michaels. The ShowStopper won back-to-back Royal Rumbles in 1995 and 1996, but he’ll be entering at #1 in this match because of his performance in 1995.
HBK entered the bout at #1 and lasted over 38 minutes to become the first man to be the first and last man standing in the match’s history. His performance brought plenty of excitement near the finish as he classically dangled over the ropes while Davey Boy Smith celebrated prematurely. Michaels survived and ultimately eliminated Smith to become the winner, making him a great choice for the #1 spot.
Honorable Mention: Chris Benoit(2014)
#2: Rey Mysterio(2006)
1:02:12. That’s the record-breaking amount of time Rey Mysterio spent in the ring in the 2006 Royal Rumble match. The career underdog entered the bout at #2 and ultimately overcame the odds by eliminating Randy Orton and HHH to win the match in honor of his late friend Eddie Guerrero.
Honorable Mention: Vince McMahon(1999), Chris Jericho(2013)