WWE Royal Rumble 2019: Ranking the 25 Most Memorable Moments in PPV History

Since 1988, the Royal Rumble has provided fans of WWE (and sports entertainment as a whole) moments and matches that have come to define the annual extravaganza and spark excitement for WrestleMania as the first official stop on the road to The Grandaddy of Them All.

From emotional championship victories to stunning fan backlash, incredible feats of perseverance and unforgettable violence, the event has housed some of the most memorable moments in WWE history.

In preparation for a 2019 event with all the makings of another newsworthy spectacle, relive these 25 moments that have become indelibly etched in the minds of wrestling fans across generations.

25. Philly Rejects Roman Reigns (2015)

If there is one thing wrestling fans hate, it is predictability.

WWE Creative found that out the hard way at Royal Rumble 2015 when the rabid Philadelphia crowd completely and mercilessly rejected Roman Reigns' victory in the event's namesake, greeting him with a chorus of boos even a surprise appearance from The Rock could not temper.

Despite a win that came when he eliminated The Authority's Big Show and Kane, Reigns was still unable to turn the boos into anything even remotely positive.

And thus began the love-hate relationship the WWE Universe has had with Reigns ever since, not to mention the red-hot (and potentially hostile) environment that accompanies the Rumble matcha and demand for fresh and unpredictable every year. 

24. The Three Faces of Foley (1998)

Never before had a Superstar appeared even twice in a single Royal Rumble, let alone three times before 1998.

Mick Foley, under the alter-egos of Cactus Jack, Mankind and Dude Love, entered the 30-man match on three different occasions. It was as Love that he experienced his greatest success, a member of the bout's final four competitors.

His performance that night, portraying three entirely different characters in the span of one match, was the most memorable of a contest that also saw The Rock break out with a 51:32 stint and three eliminations.

It also added to the match's "anything can happen" reputation.

23. Beth Phoenix Eliminates Great Khali (2010)

Eleven years after Chyna made history as the first woman to enter the Royal Rumble match, Beth Phoenix looked to etch her own name in the history books as she hit the ring at the 2010 event.

Entering the titular match at No. 6 and subsequently wowed the audience by eliminating The Great Khali. Planting a kiss on him, she pulled Khali over the top rope and to the arena floor. From there, she teed off on the loudmouthed leader of the Straight Edge Society, CM Punk, before eating a Go To Sleep and being eliminated.

The performance, though brief, added to Phoenix's credentials and was heavily featured in her Hall of Fame induction video.

22. I Quit (1999)

There are few matches more uncomfortable to watch than the I Quit match for the WWE Championship between Mankind and The Rock from the noteworthy 1999 Royal Rumble.

A violent, physical battle for the top prize in the sport saw Rock pummel Mankind, testing the masked champion's ability to absorb punishment. When Mankind did not utter the words that would set him free from the assault of his challenger, Rock cuffed his hands behind his back and unleashed a sickening 12 unprotected chair shots to the head.

The reaction of Mick Foley's family, as well as the backstage fallout captured in the 1999 film Beyond The Mat, only served to etch the nauseating beating in the minds of fans and establish its place among the most unforgettable moments in event history.

21. Making the Game (2000)

Credit: WWE.com

It seems almost unfathomable that there was a time when Triple H was not an established main event entity.

Leading into the 2000 Royal Rumble, he was very much an unproven commodity. Sure, he was in the midst of a lengthy main event push that saw him marry Stephanie McMahon on-screen and emerge as the company's top heel but his spot was hardly firmly established.

That changed at the first pay-per-view of the new millennium as The Game defended his WWE Championship against Cactus Jack in a brutal, violent Street Fight that tested his ability to take a beating and dish one out. Sporting the proverbial crimson mask, Triple H withstood a barbwire-assisted attack and delivered a vile, ruthless Pedigree to his challenger, onto a pile of thumbtacks, to retain his title.

For the first time, the audience recognized that Triple H had been tested by one of the biggest badasses and most dangerous competitors in the industry and lived to fight the next day. He not only achieved legitimacy, he earned the hardcore New York City crowd's respect.

From that night on, his place as an elite performer in WWE was undeniable.

20. Iraqi Turncoat and WWE Champion (1991)

If there was any question as to whether or not WWE was actually moving forward with the tasteless Sgt. Slaughter heel turn, the 1991 Royal Rumble answered with an emphatic "yes!"

The Iraqi turncoat who denounced his American citizenship and pledged his allegiance to Sadaam Hussein capitalized on interference from "Macho King" Randy Savage and captured the WWE Championship in shocking fashion.

At the height of Operation Desert Storm, Slaughter had proven that sometimes, the bad guys do succeed.

Worst of all, the moment proved there was no depth of tastelessness the company would not stoop for the purpose of storyline.

Of course, All-American Hulk Hogan swooped in to save the day and provide one more WrestleMania in which The Hulkster posed to close out the show so all was right with the world.

Or incredibly stale and devoid of original storytelling. 

19. An Ultimate Confrontation (1990)

As 1990 arrived, WWE champion Hulk Hogan and intercontinental champion THe Ultimate Warrior were undeniably the two most popular stars in Vince McMahon's company. Destined to clash for sports-entertainment supremacy, they came face-to-face for the first time in the Royal Rumble match and left fans eager for more.

The wrestling world came to a standstill as Hogan and Warrior engaged in a staredown, moments after fending off the likes of Shawn Michaels and Rick Martel, that set the stage for their WrestleMania VI match. A brief physical exchange culminated in a double clothesline spot and moments later, Hogan would inadvertently eliminate Warrior.

The exchange whetted the appetite of a fan base excited for the babyface vs. babyface match and more importantly, demonstrated the magic of unexpected face-offs in the annual extravaganza that continues to this day.

18. Hot Rod Strikes Gold for First Time in WWE (1992)

For eight years, "Rowdy" Roddy Piper was one of the most captivating Superstars in all of WWE. Finding success as a hated villain or beloved babyface, he was a rare crossover star whose work in film had earned him a fan base beyond the squared circle.

As the 1992 Royal Rumble arrived, though, he had unfinished business in WWE.

For all he had accomplished in the rings of McMahonland, he had never captured championship gold.

That changed at the historic event when he trapped the loudmouthed Mountie in a sleeper and rendered him unconscious. The crowd erupted as Hot Rod stood victoriously, his first (and only) WWE Intercontinental Championship fastened around his waist.

On a night when another alumnus of Jim Crockett Promotions would steal headlines for his emotional win, it is Piper's that remains one of the most feel-good moments in Royal Rumble history.

17. Santino Marella Sets a Dubious Mark (2009)

There are just some records no self-respecting Superstar wants to break.

In 2009, Santino Marella broke one of those records when he became the fastest elimination in Royal Rumble history at a pathetic one second. The comedy of the moment, coupled with Marella's reaction, helped make it one of the more memorable moments of an otherwise forgettable match.

Other Superstars to face the indignity of that record over the years? The Warlord, Bushwhacker Luker and Mo from Men on a Mission.

Quite the, um, all-star lineup.

16. A Rated R Return (2010)

In 2009, just as he had formed a tag team with Chris Jericho that was slated to become a significant part of WWE's creative plan, Edge suffered a torn Achilles tendon that would sideline him for nearly a year.

Or so Jericho thought when he started badmouthing his former partner for what he perceived to be his weakness.

The 2010 Royal Rumble match saw the unexpected return of The Rated R Superstar, who rushed the ring and immediately took out months of frustration on Y2J. After haphazardly tossing Jericho to the floor, Edge withstood the challenge of longtime rival John Cena to score his only Royal Rumble victory and earn his way to one of the many main events of WrestleMania 26.

15. Texas-Born Greats Battle for the Win in San Antonio (2007)

The 2007 Royal Rumble match featured several top stars but it was the final two that captivated fans in San Antonio and created a magical finish to one of WWE's most storied bouts.

Feeding off the support of his hometown fans, Shawn Michaels battled his fellow statesman The Undertaker, giving fans a taste of their epic rivalry for the first time in a decade. Creating drama through several near-eliminations and other teases, the two iconic performers took the fans on an emotional rollercoaster ride.

In the end, Undertaker dumped Michaels to the floor, proving the roaring approval of a hometown fan base was not enough to curb The Deadman's quest for championship gold.

Two years before their epic encounter on the grand stage of WrestleMania, Undertaker and Michaels gave fans a taste of the drama-filled war of attrition that was to come.

14. Chris Benoit Goes the Distance (2004)

The events surrounding Chris Benoit's death have erased him from WWE cannon but it would be of great disservice to the history of the Royal Rumble not to discuss the performer's superb performance in the 2004 titular match.

Forced into the No. 1 spot by then-SmackDown general manager Paul Heyman, Benoit was faced with the uphill battle of outlasting 29 other stars in order to earn the championship opportunity he had worked his entire adult life for.

In one of the most amazing performances in Rumble history, Benoit went the distance, eliminating the massive Big Show to win the Rumble match after an hour.

He would go on to win the World Heavyweight Championship from Triple H in a Triple Threat match, also involving Shawn Michaels, at WrestleMania XX. 

13. A Big, Red Nightmare for Drew Carey (2001)

In 2001, comedian Drew Carey was riding high following the success of his sitcom The Drew Carey Show and was looking to promote his upcoming improv all-stars pay-per-view. Recognizing Vince McMahon's domination of the pay-per-view industry, Carey sought advice from the billionaire owner of WWE.

Unfortunately, he did so after hitting on the boss' mistress, Trish Stratus.

McMahon encouraged Carey to steal some headlines by entering the Royal Rumble. He did and immediately regretted it after coming face-to-face with Kane.

Luckily Raven hit the ring and saved Carey from the clutches of The Big Red Machine or Carey's claim to the celebrity wing of the WWE Hall of Fame may have been a much more painful one.

12. Two Winners (1994)

Imagine being Vince McMahon in January 1994.

Fresh off a "not guilty" verdict in a steroid distribution trial, he was faced with a major issue at the top of the WWE card: payoff the months-long push of Lex Luger as the company's new All-American hero or alter booking plans to feature the fans' chosen good guy, Bret Hart.

Unable to make a timely decision, he booked the most unique finish in Rumble history: a dual winner.

After a brief exchange of right hands, Hart and Luger tumbled to the arena floor, landing at the same time and creating questions as to who really won the match. The answer? They both did.

Both Hart and Luger would go on to receive championship opportunities at WrestleMania X, the former finally defeating Yokozuna to earn his lengthy title reign and establish himself the face of WWE's new generation of stars.

11. Royal Rumble Iron Man (2006)

The untimely passing of Eddie Guerrero on November 13, 2005 shook WWE to its core and forced it to alter creative plans through WrestleMania. Having lost one of its most talented and beloved competitors, the company sought to pay tribute to him by pushing one of his best friends, Rey Mysterio.

The masked luchador would begin his unlikely journey to the World Heavyweight Championship at the Royal Rumble, where he entered the match at No. 2 and outlasted the other 29 Superstars to win and earn a title opportunity at WrestleMania 22.

In the process, The Master of the 619 set the longevity record, which would stand 12 years before Daniel Bryan broke it at 2018's Greatest Battle Royal.

The emotion surrounding the win elevated the moment exponentially and attributed to its spot on this countdown.

10. Mr. McMahon Wins! (1999)

"No chance in hell!"

Those are the odds megalomaniacal owner of WWE Vince McMahon gave his on-screen rival "Stone Cold" Steve Austin ahead of the 1999 Royal Rumble. How could the highest-ranking suit in wrestling's greatest empire feel so confident, a non-wrestler in a match with The Texas Rattlesnake? He knew more than the fans did.

Austin endured an early-match beatdown from the evil Corporation, returned to the match and fell victim to a distraction from WWE champion The Rock. The opportunistic McMahon eliminated Austin to win the match, then celebrated as if he had accomplished the feat on his own.

The post-match antics remain as memorable as the lackluster Rumble itself.

9. Ronda Rousey Debuts (2018)

The first women's Royal Rumble match, won by Asuka, headlined the 2018 event but it was the debuting Ronda Rousey that stole headlines.

Nicknamed Rowdy in tribute to late friend Roddy Piper, Rousey hit the ring and came face-to-face with The Empress of Tomorrow, Raw women's champion Alexa Bliss and SmackDown champion Charlotte Flair before partaking in the obligatory WrestleMania sign-pointing that has become a tired cliche of the event.

What was not tired was the spark Rousey's debut gave the women's division and provided it throughout the remainder of the year nor was the mainstream media coverage it attracted.

8. Ninth Wonder of the World, First Woman of the Royal Rumble (1999)

Long before WWE patted itself on the back for its use of female talent in prominent roles, and before the word "history" became an overused buzz term, Chyna etched her name in the history books as the first woman to enter a Royal Rumble match.

Arriving at No. 30, she made quick work of romantic rival Mark Henry before succumbing to a clothesline from "Stone Cold" Steve Austin.

Her stint may not have been a long one but the impact continues to be felt to this day.

On that night in January 1999, The Ninth Wonder of the World cemented her legacy in Rumble history, a legacy that is more than deserving of Hall of Fame recognition.

7. The Resurrection of the Deadman (1994)

Fans have witnessed some really...um, surreal...booking when it comes to The Undertaker but the 1994 Royal Rumble tops the list.

Moments after it took 10 heels to stuff The Deadman in a casket and preserve Yokozuna's WWE Championship reign, Undertaker appeared on the video screen, recited a promo that would make a 12th-grade goth girl ecstatic and proceeded to levitate to the heavens above.

The look of disbelief on the faces of the villains summed up the feelings of the audience, who would go approximately eight months before they would see The Phenom in a WWE ring again.

And a quarter-century-and-counting before they would forget the mind-numbingness of it all.

6. A Phenomenal Debut (2016)

For years, AJ Styles was considered by many to be the best wrestler in the world. His work in Total Nonstop Action Wrestling, Ring of Honor and New Japan Pro-Wrestling earned him that reputation and created many "what ifs" in relation to potential dream matches with WWE Superstars.

Those "what ifs" became reality in 2016 when he signed with the sports-entertainment empire and debuted at No. 3, coming face-to-face with the company's anointed "guy," Roman Reigns.

The crowd response, the magnitude of the moment and the showdown with the machine's chosen one helped make the moment an unforgettable one that both announced Styles' arrival and set him on course for a magical run that has seen him capture the WWE Championship twice.

5. Maven Stuns the World, Eliminates Undertaker (2002)

WWE wasted little time justifying its reality show Tough Enough by pushing Maven, its season one winner, way sooner than it should have.

The 2002 edition of the Rumble match saw Maven enter at No. 11 and stun the wrestling world by eliminating prematch favorite The Undertaker.

The look on his face told the story and reflected the shock and awe that overtook the WWE Universe.

Of course, his celebration would be short-lived as he caught a wicked ass-kicking courtesy of The Phenom but still, Maven created an unforgettable moment and legacy for himself that will stand the test of time.

Even if his career did not. 

4. Stone Cold's Three Royal Rumble Wins (1997, 1998, 2001)

Ok, so this might be cheating a bit but "Stone Cold" Steve Austin's three Royal Rumble wins really should be recognized as one historic and significant moment over a span of four years.

From 1997 through his final Rumble win in 2001, no Superstar was more popular, marketable or beloved among wrestling fans than Austin. The Texas Rattlesnake guided the sport to heights never before seen and rescued WWE from an uncertain future. He was the undisputed face of Attitude and a star the likes of which we may never see again.

As such, he was routinely put into a position to be prominently featured and the Royal Rumble match was no different.

In 1997, he was a surging villain whose win was used to enhance his ongoing feud with Bret Hart. A year later, he was the hand-picked future of the company. By the time 2001 rolled around, he was coming off a neck injury and faced with competition to the top spot in The Rock. His win at that particular event was a reminder to fans that they were all guests in the house that Stone Cold built. 

The only three-time winner, Austin remains the greatest competitor in the 30-man battle royal's long and illustrious history.

3. John Cena Stuns in Unexpected Royal Rumble Comeback (2008)

When John Cena suffered a complete tear of his pectoral in October 2007, fans were under the impression he would miss upwards of nine months of ring time, mostly because WWE revealed as much shortly after the injury occurred.

Without its biggest star, many wondered how WWE would fill the void heading into the new year and the march to WrestleMania 24.

It turned out, they did not have to.

In an eardrum-shattering moment, Cena shocked the world by turning up at No. 30 in the 2008 Royal Rumble, a smirk on his face. He would hit the ring, fend off the likes of Batista, Umaga and Triple H and win his first Rumble match.

It was a wholly unexpected moment and proved that yes, Virginia, surprises are still possible in the internet age of professional wrestling.

2. HBK Makes History (1995)

Before 1995, no Superstar had ever entered the Royal Rumble match at No. 1 and went the distance to win the thing.

As he would do countless times, Shawn Michaels threw history a crotch chop and altered the course of his career.

In a moment that would ensure the "both feet must touch the floor" rule would be emphasized for eternity, Michaels staved off an elimination attempt by The British Bulldog and knocked the prematurely celebratory competitor to the floor to win the contest and cash his ticket to WrestleMania XI.

The abbreviated length of the Rumble match, the shortest in event history at just 38:41, made the feat less impressive but most defintely not less significant.

1. With a Tear in My Eye (1992)

The 1992 Royal Rumble is considered by many to be the greatest of all time, for a litany of reasons. The sheer number of stories intertwined within and the epic performance of Ric Flair are just two of them. It is Flair's post-match promo, though, that stands out not only as one of the greatest moments in event history but one of the most memorable and iconic of his Hall of Fame career.

Overcome by emotion, Flair cut a promo that was both celebratory and real.

After a contentious divorce from World Championship Wrestling, Flair stood before the world the new WWE champion and uttered the words, "with a tear in my eye...this is the greatest moment of my life."

There was not a person watching who did not believe him.

For a show that has featured all-time-great performances, unforgettable moments and iconic showdowns, it is Flair's promo, just moments after winning the top prize in sports entertainment, that still ranks as the greatest moment of Royal Rumble history some 27 years after it first aired.