When Flair entered the 1992 Rumble at #3, Gorilla Monsoon took great delight in repeatedly (and annoyingly!) telling Bobby Heenan that no one had ever before entered from slots 1-5 and lasted until the final entrant (let alone won). Heenan delightedly crowed when Flair won.
Bobby Heenan[many times during the match]: THIS IS NOT FAIR TO FLAIR!
This was also Bobby Heenan's hallmark performance as a commentator.
One of the most dominating performances in Royal Rumble history took place at 1994's edition. Diesel came in at number 7, and completely cleaned house, dumping out all four of the current competitors, which included Scott Steiner, Kwang, a freshly turned Owen Hart, and Bart Gunn. From there, he would wait for participants to come out, and would eliminate the next three in very short order, which were Bob Backlund, Billy Gunn, and Virgil. It finally took a superstar the caliber of Randy Savage just to stop Diesel from eliminating each guy one at a time. Diesel came into this match as a heel sidekick to Shawn Michaels, and by the time he was finally eliminated (by four guys no less), the crowd was giving him a standing ovation and chanting his name. This was one of the first runs of this type in Rumble history, and most "dominating performances" in Royal Rumbles use this as a template (see Kane in 2001 or CM Punk in 2010). It was also one of the moments that led to the Clique's backstage takeover, eventually leading to the NWO, DeGeneration X, the Fingerpoke Of Doom and Triple H's push from hell.
To this day anyone who has this type of performance at the Rumble (clearing the ring and/or eliminating several wrestlers) is referred to as being given "the Diesel Push".
Shawn Michaels won the 1995 Rumble from the #1 spot (although to be fair, because that Rumble only had one-minute-apart entrances; it went a little over half an hour), but what really makes this Moment of Awesome can be summed up in nine words—Only ONE of Shawn Michaels' feet hit the floor.
Bradshaw hitting Mr. Ass with a Clothesline From Hell that made him do several rotations in the air in the 2000 Rumble.
In Royal Rumble 2001, Kane set a new standard for dominance in the titular match. Kane would eliminate 11 participants total, a record that stood until 2014, and in the process would...
Scare celebrity entrant Drew Carey into eliminating himself, which is not included in his body count.
Survive a weapons brawl with most of the Hardcore division.
In a Crowning Moment of Funny, the Honky Tonk Man would make a surprise entrance after Kane cleared the ring of the Hardcore guys. He would sing his entrance music, and Kane showed how much he enjoyed the performance by tuning his guitar over Honky's head and eliminating him. Kane would then shake his head, driving the point home.
Found himself on the brink of elimination by about seven guys, only for The Undertaker to enter next and re-unite the Brothers of Destruction. This of course, cleared the ring yet again of everyone except Kane and Undertaker.
Finally, Kane would make it to the Runner Up position, surviving the likes of The Rock, Undertaker, and The Big Show. It took "Stone Cold" Steve Austin with magic number 27 and a steel chair to finally get the Big Red Monster out.
Rey Mysterio Jr winning the 2006 Rumble from the #2 slot (which is equally impressive as from #1, since both #1 and #2 start the match at the same time) has to count; he lasted one hour, two minutes, and twelve seconds — the longest Royal Rumble performance to date and surpassing Benoit's two years earlier by 42 seconds— and even eliminated both Triple H (Number 1) and Randy Orton (Number 30) at the end! Especially impressive given that a small guy who specializes in high-flying moves is at an inherent disadvantage in this type of match. Most of his normal offense is not only worthless in a Royal Rumble, it's actively detrimental if he tries to use it.
Who can forget Rey's entrance? At number 2, the doors open and here we see Rey on a red convertible with an Eddie Guerrero shirt. That's how you make a Royal Rumble entrance.
The Undertaker winning the 2007 Rumble counts — both because he deserved it and he was the first #30 draw to ever win it.
Just to top everything off, the last two competitors were The Undertaker and Shawn Michaels, and the resulting battle could easily be considered a seperate match by itself
John Cena's legitimately shocking return in the 2008 Rumble is here for the sheer fact that absolutely nobody saw it coming.
To explain, Cena was out due to surgery just before his big match against Orton at No Mercy. He was said to be out for at least six months (he showed up in a sling for the Tribute to the Troops) and pretty much made everyone believe he would be out past Wrestlemania. Then he comes out, and he's completely healed. Cue everyone in the ring getting their asses kicked.
In 1989, Hulk Hogan eliminated The Warlord — who, in the process of being eliminated as soon as he stepped in the ring, set the record for the shortest appearance in a single Rumble (two whole seconds). That record stood until 2009 — when Santino Marella clocked in at just a few ticks over one second before getting eliminated by Kane.
In the 2011 Rumble, John Morrison is kicked off of the ring apron; it appears all of his hopes are lost. The Prince of Parkour, however, had other ideas — and in a move compared to Spider-Man, Morrison grabbed onto the ringside barricade and used it to get himself back to the ring steps so he could re-enter the ring. Morrison's acrobatic trickery didn't get him the Rumble victory, but that display of athletic ability damn near stole the whole show.
Also from the 2011 Rumble: Santino Marella made it to the final two by having stayed out of the ring (legally) until Alberto Del Rio had eliminated what he thought was the last competitor. Although Santino lasted longer than one second this time around, his extended break period did nothing to help him win — but his surprise runner-up finish was a great Brick Joke for everyone who hadn't been paying attention and thought Santino had been eliminated.
Everyone expected Jericho to go over as the Royal Rumble winner to set up a WrestleMania feud with CM Punk, but in the end, it was Sheamus who prevailed, no doubt surprising many fans, fella.
Cody Rhodes entering at number 4, forming a makeshift team with number 1 entrant The Miz and lasting all the way until number 30, The Big Show, enters and eliminates both. To top off a great performance for someone who some people consider to be just a midcard guy, he gets the most eliminations of the match with 6. The list of people he eliminated is as follows: Mick Foley, Santino Marella, Jerry Lawler, The Great Khali and Booker T with help from Dolph Ziggler and, last but not least, Hacksaw Jim Duggan.
2013: In a rare, legitimate surprise entrance, Chris Jericho reappeared in the number two slot and lasted well over 40 minutes until the final entrant had hit the ring before finally being eliminated. The fans were absolutely ecstatic (possibly moreso than for anything else that evening).
Kofi continues his string of amazing Rumble feats by using JBL's announcer chair to bunny hop himself back to the ring apron after ending up on the announce table, after discovering that jumping would be impossible. Sadly this would be a Shaggy Dog Story as he is immediately met with a kick to the face by Cody Rhodes upon climbing to the ring apron and is legitimately eliminated before he can even climb back in.
For the first time, an NXT Rookie, named Bo Dallas who won the Eight-man tournament Royal Rumble Fest, enters the ring in number 16. Amazingly not only he survives for nearly 20 minutes in the ring but he even eliminates Wade Barrett, NXT season 1 winner and then Intercontinental champion. He may lasted longer but Wade Barrett was so upset that he returned to eliminate him.
The next day at Raw, both him and Wade Barrett have a match and again Bo Dallas makes an upset victory over Wade Barrett.
2014: Kofi Kingston gets his third consecutive miracle elimination dodge, this time with an assist from Alexander Rusev.
Not only that, but he managed to dodge another elimination by hanging on the bottom rope just the tip of his toes... Litterally
Kane's 13-year-record finally falls as Roman Reigns eliminates 12 men, including three wrestlers (Two of them being Seth Rollins and Dean Ambrose, his own teammates) at the same time, from the Royal Rumble to set a new record for most eliminations in a single Rumble.
And he managed to make it to the final two against Batista, he lost, but still doesn't make it any less awesome.
Since Kane is essentially The Dreaded in the Rumble, his entrance is usually very foreboding...until he was on the end of a curb-stomping by CM Punk with little offense to his name and no eliminations! Kane did get revenge, however, by coming back out later and eliminating CM Punk anyway.
El Torito enters the Rumble, and even scores an elimination on Fandango.
This year's surprise entrant? None other than Kevin Nash.
Other matches on the card
In 1994, The Undertaker, after being given basically the WWF version of a Rasputinian Death at the hands of Yokozuna and several other heel wrestlers (Undertaker not letting up against about ten other men until his urn was opened) and being locked in a casket, appeared on the titantron and made a chilling speech, proclaiming he would not rest in peace. He then "floated" up to the rafters, crossing over into the afterlife presumably.
This has been inducted into WrestleCrap, for the record.
You can see this on the DVD extras; after the match, Triple H is taken backstage onto a stretcher and is all bloody and messed up. And one of the first things he does is ask someone to find his parents, who are in the audience, and let them know he's okay.
Kurt Angle was in full-on Smug Snake mode and was yet to have been defeated in singles competition. He comes out at the opening of the PPV and delivers some backhanded comments about Patrick Ewing and the Knicks (it was Madison Square Garden and Angle's gimmick at the time was to obliviously insult the fans via their hometown sports stars). Then, his mystery opponent for the night appears: Taz. Debuting at the Rumble, Taz proceeds to squash Angle with a number of suplexes and the Tazmission, ending Angle's undefeated streak and delighting the New York crowd to no end.
The Dudleys vs the Hardys capped off their typical CMOA match with Jeff performing a Swanton Bomb from the balcony through Buh Buh and a table.
The 2003 Rumble saw Scott Steiner vs. Triple H for the World Heavyweight Championship, in one of the worst matches in the company's history. Immediately after that, Chris Benoit and Kurt Angle battled for the WWE Championship that, not only took the piss out of the previous debacle, but was a Match of the Year candidate. As unintentional as it was, it was a huge apology, with HHH/Steiner bordering on Let Us Never Speak of This Again territory.
From the 2004 Royal Rumble event: Shawn Michaels and Triple H put on a classic Last Man Standing match. It's remembered for being not only a nail-biter of a match, but for its double-disqualification ending (in Philadelphia, of all places). It would have stolen the show had Benoit not put on such an amazing performance.
2013 brings us The Rock and CM Punk for the WWE Championship. Marking over 10 years since The Rock has challenged for a WWE title and CM Punk enjoying the longest WWE Championship reign in the past 25 years (434 days), the stakes were high. The Rock swore that he would come to the event and take Punk's title with the added stipulation that any interference from rogue unit The Shield would cause Punk to be stripped of the championship. After an intense contest, the lights in the arena go black and The Rock is dragged outside and slammed through the announce table by an unseen Shield. Punk scores the pinfall from the interference but Vince McMahon declares that, despite being dark, The Shield interfered and he would strip Punk's championship. The Rock refuses to let the match end like this, demands a restart, and pins Punk with the People's Elbow to win the WWE Championship for the first time in a decade and ends Punk's historic reign as champion.