Anytime a Heel character is trounced in a way that instantly enters the record books. One instance that was truly for the ages occurred at the 2009 Royal Rumble Match to Santino Marella. He entered the contest, climbed over the ropes - and was instantaneously knocked back over the ropes by Kane, resulting in the shortest ever Royal Rumble time of one measly second. Predictably, Marella suffered a Villainous Breakdown as a result and screamed "I WASN'T READY!"
When Santino Marella is in Butt Monkey mode, this happens to him a lot, like when he hilariously tried to imitate Melina's infamous splits entrance, only to injure his groin and fall out of the ring.
Repeated at Money In The Bank 2012, where Dolph Ziggler attempts to cash in on Sheamus, and Sheamus knocks Ziggler out cold with the Brogue Kick as soon as he gets in the ring.
The epic fail for Vince actually started in the Punk-Cena match itself. Cena had Punk locked in the STF for the second time in the match, then had his corporate stoogeJohn Laurinaitis try to go and get the referee to call the bell. Seeing this out of the corner of his eye, Cena left the ring, decked Johnny Ace, and took ten seconds more to tell Vinny Mac he wanted to win the right way before getting back in the ring. Cue GTS and pinfall, leading to the above situation with Del Rio.
Whenever someone botches a move. For example, at Sacrifice 2008, AJ Styles attempts a top rope splash on BG James, but misses by a mile and lands on his face even though James didn't move out of the way.
Brock Lesnar botching his shooting star press at Wrestlemania. Even though he screwed up the move, it's still an incredibly epic moment since he landed on his neck in a way that probably would've killed anyone else, then he gets up and still manages to win the match.
In the beginning of Tough Enough 2011, the new recruits declare they are ready to be new wrestlers, but are revealed to be so out of shape that they can't even run a few laps around the ring without getting out of breath and ready to collapse.
The infamous debut of The Shockmaster in WCW. Hyped for months with a Galactic Conqueror gimmick, he finally debuts with a Dynamic Entry by plowing through a wall... and he stumbles and collapses. His helmet falls off and he looks like a total fool as well as revealing himself to be Fred "Tugboat/Typhoon" Ottman.
Late in 2005, Goldust and Vader return and help Jonathan Coachman ambush Batista and beat him up. The trio celebrate and try to leave the ring... and Vader stumbles and falls to the floor. He shouted expletives as he couldn't get up on his own and had to be helped up by his comrades.
Kevin Nash suffered a biceps injury in March of 2002, and after several long months of rehab, and promotion of his impending return on WWE's part, he made said return in a 6-man tag team match in July..... and suffered a quadriceps tear within ten seconds of tagging in. Nash never quite lived that one down.
At WrestleMania XXUltimo Dragon lived out his dream by wrestling at a WrestleMania at Madison Square Garden. A shame he slipped and nearly fell flat on his face twice during his entrance.
Sting faced Bobby Roode for Roode's world title at TNA's Victory Road pay-per-view in 2012, in a No Holds Barred match. During the course of the match, a steel chair was set up in the ring by Roode, but before he could slam Sting into it or whatever his plan was, Sting started making a comeback. Finally, Sting was getting ready to hit Roode with his Finishing Move, the Scorpion Death Drop. However, Sting evidently did not notice that the steel chair was still in the ring and right behind him. So when Sting threw himself backward to drive Roode's head into the mat, his own head smacked into the seat of the chair. Yes, Sting knocked himself out, which led to him losing the match. Here is a gif of it happening.◊
The "This is Your Life" segment of November 14, 2011 episode of RAW with Mick Foley and John Cena. It's was like a car wreck you can't help but keep watching, no matter how painfully bad it is. Every guest, which were his old little league coach, his old tag team partner Bull Buchanun, and his own father, that came for the segment just turned the crowd more and more against Cena, to the point where even Cena Lampshaded how bad the segment was, calling it worse than the Shockmaster, then stating it was one of wrestling's greatest catastrophes, right up there with the Gobbledy Gooker. It was probably the first time that Cena was ever glad to see The Rock, who proceeded to go out to the ring, Rock Bottom Foley, and leave immediately afterwards, ending the horrendous segment. It was probably due to remembering his own "This is Your Life" segment with Foley (which is the highest-rated segment in RAW history) that Rock took pity on Cena and decided to end it before it got any worse.
The Gobbledy Gooker, arguably the worst Epic Fail of all of professional wrestling history. After carting a giant egg (complete with a nest) to events all around the country, it did manage to build up some intrigue with WWF's younger audience. Come Survivor Series 1990, what should finally hatch out of the egg but... a guy in a goofy-looking turkey costume.note It was actually Hector Guerrero. It's so infamously bad, that WrestleCrap named the Gooker award after it, and annually awards it to the promotion with the worst Epic Fail angles in wrestling of that year. Among them includes David Arquette as WCW Champion, Katie Vick, Chavo Guerrero's feud with Hornswoggle, the NEW Monday Night Wars, and the Claire Lynch angle in TNA, which, while entirely different in storyline, easily became the Katie Vick of TNA.
The "Kennel From Hell" match between Big Boss Man and Al Snow at Unforgiven 1999. They fought in a Hell in the Cell with a regular steel cage inside, with "vicious attack dogs" between the two cages. Unfortunately, they completely forgot to get vicious attack dogs. The dogs completely ignored the two combatants and started peeing, pooping, and even mating around the ring. The actual match sucked as well.
Austin Aries trying to apply the scorpion death lock on Sting during the March 15th 2013 Impact in Chicago only to keep screwing up long enough for Sting to recover and escape just before Aries asked him how to do it.