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The Royal Rumble match is all about survival, even more than Survivor Series. Every superstar who enters the match hopes to survive until the very end and book his/her spot in a World Title match at WrestleMania. Every year, a total of 60 superstars enter two mammoth matches, but only two earn the right to call themselves the winner of the Royal Rumble match.
Another aspect that matters in the Royal Rumble is the entry number of the performer. While the superstar who enters the match in the last few spots can be considered lucky, given that they have to stay in the match for a lesser amount of time, a late spot in the match doesn't always guarantee a win.
That is not to say that there haven't been superstars who won the Royal Rumble despite being among the final few participants to enter the match. On the flip side, there have been a handful of Superstars who entered the match early, lasted for a significant amount of time, and somehow emerged victorious.
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In fact, there have been exactly 10 such superstars, over the past 33 years, who won the Royal Rumble match with a performance lasting more than 30 minutes. As we enter the last few days before the 34th annual Royal Rumble, here are the 10 Royal Rumble winners with the longest stay in the Rumble match.
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#10 Drew McIntyre - 34:11 (Royal Rumble 2020)
Being the main event of the latest Royal Rumble PPV, I'm sure every wrestling fan remembers the Men's Royal Rumble match from 2020 pretty well. Brock Lesnar dominated the first half of the match with arguably the most brutal performance in history. Plus, Edge's return, followed by Drew McIntyre's victory, were the highlights of the second half.
Not only was McIntyre the winner of the match, but he also had the longest stint in the match. Between the elimination of Brock Lesnar and Roman Reigns, McIntyre stayed in the match 34 minutes and 11 seconds, which is currently the 10th longest stint in the Royal Rumble that resulted in a win.
In addition to Lesnar and Reigns, McIntyre also dispatched The Miz, Seth Rollins, King Corbin, and Ricochet from the match. His winning performance catapulted him to superstardom, leading to two WWE Title reigns in the past 10 months.
#9 Shawn Michaels - 38:41 (Royal Rumble 1995)
WWE's decision to reduce the time interval between participants to 60 seconds instead of 90 in the 1995 Royal Rumble match is often remembered in a polarized way by the fans.
However, one can't argue with the fact that the match was presented and brought up in the best possible way. Shawn Michaels and The British Bulldog, the number one and number two entrants in the match, were also the last two participants and this led to some great storytelling.
Michaels was the real highlight, though, eliminating eight superstars from the Royal Rumble match during his stint of 38 minutes and 41 seconds. The way he saved himself from elimination by only touching the floor with one foot set the precedent for several future saves.
Even though Davey Boy Smith spent an equal amount of time in the match, it was Michaels who emerged as the biggest superstar from the match as he became the first performer to start the Royal Rumble and win the match; A feat that has been repeated only three times in the subsequent 26 years.
#8 Seth Rollins - 43:00 (Royal Rumble 2019)
The Men's Royal Rumble match from 2019 was one of those editions where only a couple of performers had a legitimate chance of winning and, unsurprisingly, two of these men ended up being the last two Superstars in the match - Seth Rollins and Braun Strowman.
After his in-ring exploits from 2018, Rollins was the favorite the win the Men's Rumble match, and he accomplished the feat with his best performance in the 30-Man Match. Entering the match at #10, The Kingslayer stayed in the match for exactly 43 minutes before he eliminated Braun Strowman with a Curb Stomp on the ring apron to win the Royal Rumble.
Apart from Strowman, he also dispatched Elias and Bobby Lashley, two Superstars with whom he had feuded extensively over the last 6 months, and also took a beating at the hands of the latter. Despite all that, he put on a gutsy and strong performance to book a ticket to the Universal Title match at WrestleMania, which he won after defeating Brock Lesnar, in less than 3 minutes.
#7 Shinsuke Nakamura - 44:38 (Royal Rumble 2018)
The 2018 Men's Royal Rumble match can easily be considered the best Rumble match in recent memory. It had everything you need for a memorable Royal Rumble - A monumental return by Rey Mysterio, an Iron Man performance by Finn Balor, the comedy bits from Heath Slater, and a show-stopping, multi era face-off between six brilliant performers.
The best moment of the match, however, was Shinsuke Nakamura's victory, who finally broke the jinx of unpopular Royal Rumble winners, to give the fans a moment to cherish for years to come. His performance in the match was not short of spectacular as well, as he crawled through the field, after entering the match at #14, to book his ticket to WrestleMania 34.
His stay of 44 minutes and 38 seconds was the longest duration for a winner in the Rumble match in a decade. He eliminated three superstars during his marathon performance, but what makes his win even more special is the fact that he eliminated John Cena and Roman Reigns, two of the biggest stars in WWE history, in succession to win the match.
Even though the follow up to this Royal Rumble win was not even close to what the fans were expecting, Nakamura's victory in this highly contested Royal Rumble is still the peak of his WWE career.
#6 Stone Cold Steve Austin - 45:07 (Royal Rumble 1997)
Just like the 1996 King of the Ring and WrestleMania XIV, the 1997 Royal Rumble can actually be considered one of the landmark moments in the career of Stone Cold Steve Austin. It was in the Alamodome in San Antonio that the Rattlesnake had probably the most dominant performance of his career, even though it was not without some shenanigans.
On the verge of breaking out as a bonafide main event star, Austin broke plenty of records en route to his victory in the 1997 Royal Rumble match. Entering the bout at number five, Austin went on a rampage as he accounted for a total of 10 eliminations, joining highest number back then, during his stay of 45 minutes and 7 seconds inside the ring.
Until the time Bret Hart, who entered the match at #21, made his way to the ring, Austin was throwing superstars out of the ring as if they were pebbles. Luck was also on the Texan's side as a distraction for the referees meant he re-entered the match even after getting eliminated, and eliminated three more superstars after that.
Had that not been the case, Austin would have only had two Royal Rumble wins to his name, and his legendary winning performance would not have been a part of this list.
#5 Randy Orton - 48:30 (Royal Rumble 2009)
Randy Orton's victory in the 2009 Men's Royal Rumble match kick-started what, along with his current run, can easily be called the best heel run of his career. With Cody Rhodes and Ted DiBiase teaming with him as Legacy, Orton used his Royal Rumble victory to not only start a feud with the McMahon family, but also became the top heel in the organization.
Entering the match at number eight, immediately after Triple H, the Legend Killer used the Royal Rumble match to further intensify his rivalry with the McMahons. Along with his stablemates and Triple H, Orton made it to the final four of the match, dispatching Big Show and Kane in the process.
Despite facing a late resurgence by The Game, who eliminated Rhodes and DiBiase, Orton threw him over the top rope to win his first Royal Rumble match. His stay of 48 minutes and 30 seconds is still the longest time he has spent in a Rumble match, and will forever be remembered as one of the finest heel victories in the history of Royal Rumble.
#4 Mr. McMahon - 56:38 (Royal Rumble 1999)
Vince McMahon's victory in the 1999 Royal Rumble Match, let alone his appearance in the match, is something that fans have not cherished a lot over the subsequent years.
After all, it was the peak of WWE's most famous period. There were plenty of more talented superstars in the match who could have benefitted a lot from the win, and McMahon didn't actually wrestle in the Main Event of WrestleMania 15. However, one can not take away the fact that The Boss had one of the longest stays in the match, not only by a winner, but by any performer in the Royal Rumble history.
Entering at number two, McMahon spent 56 minutes and 38 seconds in the Royal Rumble match, the same as the number one entrant Steve Austin, who was the last and only person eliminated by The Boss in the match. He spent most of the match outside the ring, mostly at the announcer's table, and was inside the ring only when he was getting beaten by Austin.
McMahon's victory made him the first superstar to win the Royal Rumble match with a solitary elimination to his name, a feat that was repeated by Randy Orton in 2017, and he had the second-longest stay in winning performances at that time.
#3 Ric Flair - 1:00:02 (Royal Rumble 1992)
We now enter the category of winners who actually defined the Iron Man performance in the Royal Rumble match, by staying in the match for more than one hour. Who better than Ric Flair to be the first superstar on this list?
By 1992, Flair was arguably the biggest superstar on the planet, on par with Hulk Hogan, and he only solidified his stance with a performance that is still considered the gutsiest one in the history of the Royal Rumble.
Breaking all the longevity records set by the participants in the first four Rumble matches, Flair entered the match at number three and stayed between the ropes for an unprecedented one hour and two seconds.
This was eight minutes more than the previous record set by Rick Martel in 1991, twenty-six minutes more than Roddy Piper, the participant with the second-longest stay in that match, and a whopping 38 minutes more than any previous winner.
With five eliminations to his name, including the likes of Randy Savage, Hulk Hogan, and Sid Justice, The Nature Boy's Royal Rumble and WWF Championship victory kick-started a period that he refers to as the favorite time of his legendary career.
Even though his record of most time spent was broken the very next year by Bob Backlund, it took 12 more years for someone to win the Royal Rumble match by staying in the match longer than Flair did in 1992.
#2 Chris Benoit - 1:01:35 (Royal Rumble 2004)
Only two superstars have won the Royal Rumble match from the number one spot, including WWE Hall of Famer Shawn Michaels.
WWE officials have tried their best to remove Chris Benoit's performance, and the Royal Rumble match, from 2004 from the history books and the minds of the fans by having the commentary team use the above words every year during the Rumble season. But it is just impossible not to talk about this monumental moment while talking about some of the greatest individual performances in the event's history.
Benoit was the third superstar to win the Royal Rumble match after being one of the two superstars to start the match, and was the second one to draw number one and win.
The Rabid Wolverine went from bell to bell, for 1 hour, 1 minute, and 35 seconds, tackling the challenge from the likes of Randy Orton, Chris Jericho, Kurt Angle, and The Big Show to book his ticket to the main event of WrestleMania XX.
He eliminated six Superstars from the match, including Big Show, whose elimination as shown in the above image is often considered one of the most innovative eliminations in the match's history.
#1 Rey Mysterio - 1:02:12 (Royal Rumble 2006)
Underdogs overcoming the odds to win the Royal Rumble match - This is a storyline that we have seen several times. The likes of Ric Flair, Chris Benoit, Shinsuke Nakamura, and Seth Rollins come to mind when we try to remember the Superstars who emerged victorious, despite being considered the underdogs.
However, there hasn't been a better underdog story in the Royal Rumble match than Rey Mysertio's arc to the Rumble win in 2006.
The fact that Mysterio's victory came in the aftermath of Eddie Guerrero's untimely death does raise the question of whether Mysterio was always scheduled to win the match or not. But, irrespective of the answer to that question, one can boldly say that Mysterio gave probably the best performance of his life that day.
Entering the 2006 Royal Rumble match at number two spot, Mysterio fought and crawled through his opponents for 1 hour, 2 minutes, and 12 seconds, eliminating five superstars, before he last eliminated Randy Orton to seal his ticket to a World Title match at WrestleMania 22.
Not only is his performance the longest individual stay in a winning performance, but it is also the longest stay by any performer in the Rumble match if we don't consider the Greatest Royal Rumble match among the conventional Rumble matches.
