Triple H
When Triple H first won the Royal Rumble it was after he would come back from an injury that kept him out of action to miss the entire WCW and ECW invasion angle. And although he was injured as a heel, the fan reaction to his return where he announced he was entering the Rumble was so huge a win in the Rumble was guaranteed. He would then go on to win the main event of WrestleMania X8, defeating Chris Jericho to become undisputed WWE Champion.
Triple H’s second Rumble win was the second time that the World Title was contested in the actual match itself. In 2016 Roman Reigns was the World Champion and would enter the Rumble and put the belt on the line. After starting the match Roman would go the distance only to be eliminated by Triple who would then take out Dean Ambrose last to capture the Championship.
Hulk Hogan
Back in the era when the WWE hadn’t figured out that the prize for winning the Royal Rumble could be a WWE title shot at WrestleMania, they simply had their biggest stars in the large scale match. In 1990 Hulk Hogan was still the biggest star in wrestling and would win match to further prove his dominance.
The next year in 1991, Hogan would win again, and would go on to face the WWE Champion Sgt Slaughter in the main event of WrestleMania, although this was just coincidence and not because of the Rumble victory.
In this era Hulkamania was truly unstoppable and it seemed like he would win it every year at this rate. Alas for Hogan, his reign of Rumble wins would stop at 2 as his 3rd place effort at the 1992 Rumble would be his last before leaving the WWE for WCW.
Shawn Michaels
After Hulk Hogan, Shawn Michaels was the second man to win the Royal Rumble twice. His first victory came when he was a heel in 1995, where he was also the first man to enter the Royal Rumble at number 1 and go the full distance to win the match.
His victory wasn’t without a couple of elements of controversy as this Rumble saw the wrestlers enter every 1 minute which was the shortest interval between entrants to date. Also, the number 2 entrant, The British Bulldog had seemingly won after throwing HBK over the top rope and even had his music played, but then Shawn got back in the ring and eliminated Bulldog to get the victory. After this confusing moment happened a camera angle showed that Michaels had gone out the ring but only one of his feet had touched the ground which meant he could re-enter. Of course, the fact that they played Bulldog’s music to announce him the winner meant this stank as this aided Michaels victory as Bulldog had let his guard down.
Michaels would win the Rumble again the very next year in 1996 and this time HBK was a baby face and would go on to fulfil his boyhood dream to become WWE Champion at WrestleMania 12. Last eliminating Diesel, HBK had a huge victory which also saw him eliminate eight opponents which equalled his efforts from the year before despite coming in much later in the match at number 18.
Ric Flair
What can be said about Flair’s Rumble victory other than the match was something of a masterpiece. This being the fifth Rumble to air on screen, the WWE had finally really got the hang of the event. With the WWE Championship vacated after controversy between Hulk Hogan and The Undertaker in late 91, the match had huge stakes for the first time with the WWE Championship up for grabs. Ric Flair would enter the match at number 3 and go on to win the whole thing and the title. Despite being a heel, how could any fan not respect the level of stamina to go what was at that time an unheard of distance in the Rumble match.
Stone Cold Steve Austin
In a record that may never be equalled or broken, Stone Cold Steve Austin would win the Royal Rumble a staggering three times.
The first time came in 1997 under controversial circumstances. With a brawl on the outside distracting the referees, Stone Cold was eliminated by Bret Hart, but able to dive in without his elimination being noted by the refs. Austin would then eliminate Bret Hart and be announced the winner. This was a huge step to the building of Steve Austin as the superstar he became after his famous Austin 3:16 promo at the 96 King of the Ring and followed up at the 97 WrestleMania in his famous double turn match with Bret. Sure, Austin wouldn’t get the traditional WWE Championship match at Mania following his first Rumble win, but what he did get was arguably bigger for the Rattlesnake.
His second win came the next year and with the WWE moving firmly into the Attitude era, Austin was the man to lead the revolution and would have one of the most iconic WrestleMania main events ever against HBK with Mike Tyson as special ring enforcer.
His third Rumble win wouldn’t come the next year in 99 where he would come second to Vince McMahon himself, but would come in the year 2001 after missing the 2000 event due to injury.
Every Rumble Austin won was a huge victory and massive for the WWE and WWE fans. The fan’s love for Austin and wanting him to take it to the man and beat up the boss was a huge driving factor for the Attitude era. That his final Rumble win would take him on to his iconic second WrestleMania main event with The Rock when The Rock had hit the peak of his WWE run made it all the better.
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