1991 - Entry #27 was Bushwhacker Luke who, after doing the Bushwhacker's signature Silly Walk to the ring, was grabbed by Earthquake mid-stride and tossed out. This barely slows Luke down, and he simply continues the walk back out of the arena.
1992 - Just prior to interviewing Shawn Michaels before the Rumble match for the WWF World Title, Sean Mooney nearly gets down when The Barbarian gruffly walks past him.
Jerry Lawler's entry into the 1997 Royal Rumble. He was already sitting at the commentator's booth when his music began to play, and the last thing he said to Vince was "It takes a King,". He climbed into the ring and was almost immediately knocked out by Bret Hart. He walked back to the commentator's booth and said "to know a King." And for the rest of the Royal Rumble match he forgot he was ever in it.
Kaientai's repeated interference in the 2000 Rumble. One instance led to Gangrel throwing Taka Michinoku out of the ring, causing Taka to land on his face. Jerry Lawler repeatedly requested to watch the replay throughout the rest of the Rumble.
Kane eliminating the Honky Tonk Man in 2001 immediately after he sang his song— grabbing his guitar and smashing him over the head with it. And then shaking his head slowly.
2002 - Austin and Triple H were in the ring with the Hurricane and the Hurricane got the goozle on both of them, prepping them for a chokeslam. They sold it like he's the Undertaker or Kane for about five seconds before they both looked at each other and realized they're being choked by the freakin' Hurricane. Just as it dawned on the Hurricane that he just grabbed the necks of the two most decorated wrestlers of the Rumble that year, they grabbed him by the back of the neck and threw him over the ropes.
John Cena entered the 2003 Rumble with what is quite possibly his best Heel rap ever, where he manages to rhyme "explain to ya" with "Wrestlemania" and the thing ends with the brilliant line, "my style is like a swollen penis, you can't beat me."
Maven, who in the 2002 Rumble became famous for eliminating The Undertaker with a dropkick, tried to repeat the feat in 2003, and failed miserably.
2004 - Chris Benoit and Randy Orton had just eliminated several guys in a row and then collapsed from exhaustion. The announcers mentioned that the next person to come out would have a huge advantage. But that person turned out to be Ernest "The Cat" Miller, who decided to dance to his theme music alongside his ostentatiously-wigged manager, Lamont, instead. Benoit and Orton were not amused, and threw both of them over the top rope.
Made even funnier by Lamont's wig coming off in Benoit's hand in mid-elimination. One recap listed "Lamont's wig eliminated" in the timeline.
2005 - Eddie Guerrero and Ric Flair were drawing their numbers to enter the rumble. Flair seemed overjoyed with his number. Eddie pulled Flair in for a congratulatory hug, and swiftly left the room. Only a little later did Flair find out that Eddie had somehow swapped numbers with him during the hug! Later on Flair and Teddy Long were able to track down Eddie, and Teddy Long forced Eddie to give Flair his number back. But, after Eddie had already handed the number over, Teddy was still holding his hand out. Eddie shook his hand, but Teddy still wasn't impressed. "Hand it over, playa." Eddie then sheepishly handed over Flair's wallet. Cue Eddie making a speedy exit, and Flair becoming absolutely enraged.
We later found out during the rumble that Eddie had drawn number one, while Flair had drawn number 30.
Eddie and Chris Benoit began the rumble with an exhibition of mat wrestling, when Tough Enough winner Daniel Puder comes down at #3, grabs a mic and boasts that he'll be the first Tough Enough winner to win the Royal Rumble, to Eddie and Benoit's consternation. As soon as he enters the ring, the two veterans immediately begin laying into him with stiffWhooooooooo! chops, taking turns abusing the rookie. Just as they begin throwing him around, notorious rookie hazer Hardcore Holly enters next and right away begins laying the chops himself. This eventually devolves into the three taking turns holding Puder's arms behind while the others chop him up. This is made funnier by Eddie's reactions the entire time, and even the famously stoic Benoit starts playing it up. Puder is mercifully eliminated after an Alabama Slam from Holly.
With eight guys in the ring, four from SmackDown! and four from Raw, they temporarily split up, then a SmackDown! versus Raw fight ensues. When Muhammad Hassan enters the Rumble, however, all the fighting in the ring stops, and all eight superstars immediately gang up on him, setting him up for Rey Mysterio to hit him with a 619, then six of them work together to dump Hassan out of the ring.
Kurt Angle came in with a full head of steam and just starts suplexing everyone until he got to Shawn Michaels who super kicked him out of the ring. That was Angle's shortest time in the rumble.
2008 - The Miz getting eliminated by Hornswoggle. You're just paying your dues, Mike.
2011 - Santino Marella, who at this point had averaged about 15 seconds in two Rumble matches, would get knocked out by Sheamus within 20 seconds of his appearance and would have the fortune to fall under the bottom rope. This became a Brick Joke when later on, Alberto Del Rio would be celebrating his apparent victory only to turn around and get hit the with The Cobra! Unfortunately for Santino, he would take a few seconds too long to celebrate, and would instead go home as the runner up when Del Rio reversed his elimination attempt.
The New Nexus lead by CM Punk. He's very happy after having four members including himself. He's acting all and mighty with a nice troll face until Khali's music hits in. What he does next? Hide behind his fellow members.
Not to mention, CM Punk is still scared in facing Khali in past Royal Rumble matches starting from the first time Khali enters the Royal Rumble in 2007.
2012 - .The Cobra vs. Mr Socko... After the elimination of Ricardo, these two have a standoff and decide to take out their own 'weapons' and wear it. It's more funnier that once Epico enters the ring and interrupt their battle, he gets Santino's Cobra and eliminated by Foley's Mr Socko in just 11 seconds.
Ricardo Rodriguez entering in Alberto Del Rio's place, driving The Alleged Car and imitating Alberto's entrance. This has to go down as one of the funniest swerves ever, since Alberto had been Put on a Bus several weeks before because of injury and injured superstars have had a pattern of returning at the Rumble.
Several things made this funnier. First off being that the fans were genuinely entertained and several "Ricardo!" chants broke out. Second, Ricardo (with Mick Foley's help) actually got an elimination. Third and perhaps most hilariously, he was unfortunate enough to end up with a solid, all-white set of ring gear, giving the impression that he was wrestling in his underpants.
All three announcers revealed they have entered. However for Michael Cole's case, he was very happy he entered until his expression on his face change when Kharma returned. To make this more epic, he was eliminated by Booker T and Lawler in order to save him from being eliminated by Kharma
2013 - The Godfather's cameo in the Rumble. He came out with two of his hoes, removed his coat, sunglasses and hat, entered, and 5 seconds later, was eliminated by Ziggler. All while his music still played! Then, his reaction, which was merely a shrug, take the ladies by the arms and walk back again. All while his music still played!
Team Hell No elimination. After Team Hell No eliminates Khali, Daniel Bryan eliminates his own partner Kane. Knowing it's the rumble, Kane is still in shock while looking at his partner. But it was short-lived for Daniel as he was sent out of the ring by Antonio Cesaro but Kane catches Daniel Bryan. Daniel tells Kane to put him back but he refuses as both Kane and Daniel keep yelling "NO!" And "YES!". After that Daniel was trying to go back in the ring but Kane decides to drop him down instead, eliminating him.
2014 - This extended version of the commercial for the Royal Rumble is full of hilarious moments.
And when El Torito came and managed to take out Fandango before setting his sights on CM Punk, who just looks at dumbfounded at this sight and turns to Dean Ambrose, one of three guys sent to make sure he doesn't win and asks him something along the lines of "Tell me I'm not the only one who sees this, right?" and Ambrose for a quick second seems to be as confused and shrugs.
JBL is introduced at #24, whereupon he stands up from his spot at the announce table, climbs into the ring, hands his coat to Michael Cole... and is promptly eliminated by Roman Reigns, whereupon he reassumes his spot at the table and continues on commentary as if nothing had happened.