Number 3 Shawn Michaels
The Heartbreak Kid won the Royal Rumble in both 1995 and 1996, making him the second person after Hulk Hogan to not only win twice, but to win twice in back to back years.
In his first win, Shawn started the Rumble in the number 1 position compared to the British Bulldog who entered at number 2. This was an interesting era for the WWE and some of the choices made in this Rumble are questionable as Shawn was the heel, but the first person to go the distance from 1 to the end and win which in a anything goes rules match kinda just showed that he was better than anyone else.
Add to this that the ending actually saw the British Bulldog pose in victory with his music playing after apparently eliminating Michaels, only to be quickly eliminated by Shawn who it transpired had managed to land with only one foot going on the ground outside the ring, and therefore not genuinely out. This shock twist ending certainly upset a lot of fans of the baby face Bulldog, but much to the heel Michael’s credit, was not cheating in any way. Bulldog was screwed here, not by HBK, but by the sound guy for playing his music early when the match hadn’t actually ended.
This win for Michaels though still impressive also had the downside that the WWE had reduced the entrances in the match to every 1 minute meaning that Shawn won the match going from 1 to 30, but was in the ring less than Ric Flair who had previously won after starting at number 3.
Shawn’s first win would see him take on Big Daddy Cool at Mania only to lose, which does take away a little from this victory here.
The next year Shawn would again reign victorious in the Rumble, and this time as the baby face who would go on to face the also baby face Bret the Hitman Hart at Wrestlemania 12. This story actually played out much better from start to finish as the WWE were able to tell Shawn’s ‘boyhood dream’ to become champion and saw him beat the odds of winning the Rumble a second time, and though he wasn’t in the match as long, he did last an impressive 26 minutes and eliminate the most competitors with 8 eliminations overall. This gave him a strong build into the Iron Man match with Bret which famously went to overtime in the 60 minute classic where Shawn would leave victorious.
