Wrestling’s 10 Most Shocking Moments

The wrestling world has been filled with plenty of shocking moments over the decades, but which moments that made fans gasp with excitement – or dread – make our list of Wrestling’s 10 Most Shocking Moments.

Although wrestling is sadly littered with darker tales of shocking moments, for this list we’ve stuck with things that have happened on shows that have affected storylines going forward or were outrageous in their time for one reason or another.

When you think of shocking moments in wrestling fans of a certain vintage might instantly have the image of The Shockmaster careering through a wall and losing his helmet in the process in WCW. But this list starts with a different type of shocking the system.

10. All Elite’s New ERA Begins

Bryan Danielson AEW

In AEW’s relatively short tenure, the company has played host to several moments that have left fans’ mouths agape. None more so than at the end of their All Out pay-per-view in September 2021 when not one, but two former champions from WWE announced themselves as All Elite.

While CM Punk’s return to wrestling could have made this list, the set up to the show in Chicago left the vast majority of people with no doubt that Punk was going to make his AEW debut. While rumours swirled about what was going to happen at All Out, very few people expected it to play out the way it did.

All Out was headlined by Kenny Omega defending his AEW World Championship against Christian Cage. Come the end of the night Omega had retained and was in a celebratory mood as he took the microphone while flanked by his Elite cohort.

As Omega decried that no living person could take his title away, the lights went out, and Adam Cole (BAYBAY!) made his AEW debut to a thunderous roar of approval from the crowd. With many aware of how Cole’s time in Bullet Club came to an end – The Young Bucks turned their back on his and sided with Omega – the tension was palpable. Cole soon revealed his intentions as he nailed Jungle Boy who had accompanied Cage to the ring along with Luchasaurus with a vicious superkick.

As an emboldened Elite continued their assault on Christian Cage and Jurassic Express, a bigger roar was to come as Wagner’s Flight Of The Valkyries hit, and Yes! Yes! Yes! Bryan Danielson revealed that he was also All Elite.

9. Pillman’s Got A Gun!

Brian Pillman

On November 4th, 1996 the then-WWF may well have been a long way off entering the Attitude Era but things took a turn to the wild side when Brian Pillman pulled out a gun on Monday Night Raw.

Brian Pillman and Stone Cold Steve Austin have a history dating back to their WCW days as young up-and-coming tag team The Hollywood Blondes. When Pillman joined the World Wrestling Federation in 1996 his old partner was a man possessed and on the hunt for a showdown with Bret ‘Hitman’ Hart at Survivor Series.

On an episode of WWF Superstars, Austin snapped when Pillman mentioned Hart’s name and attacked his former partner. Austin left Pillman with a serious ankle injury – in reality, caused by a bad car crash – as he gave rise to a new turn of phrase in the wrestling world as he “Pillmanized” Pillman’s leg with a steel chair.

This takes us to the 4th of November when Pillman was set to do an interview from his home but Austin was on his way to crash the party. Throughout the night Vince McMahon spoke to Austin live on the phone and Kevin Kelly was on hand at the Pillman residence providing updates on the situation throughout the night.

It was during Kelly’s sit down with Brian Pillman and his wife Melanie that Vince McMahon interjected to inform them that Austin was “circling the neighbourhood” which prompted Pillman to offer the infamous line “when Austin 3:16 meets Pillman 9mm Glock I’m gonna blast his ass straight to hell.”

Austin was then seen attacking Pillman’s friends outside the house and eventually smashed his way in through the back door only to be confronted by Brian Pillman pointing a gun straight at him before the satellite feed conveniently dropped out.

When the action returned to Pillman’s house, Kevin Kelly confirmed nobody had been struck by any of the “explosions” before Austin returned with Pillman pulling out his firearm once again and screaming “I’m gonna kill that son of a b*tch” and audibly telling his friends restraining the Texas Rattlesnake to “get out of the f*cking way.”

Such was the backlash to the angle, a chastened Vince McMahon appeared on the following week’s edition of Livewire where he apologised and admitted they had gone “overboard” with the storyline in an attempt to draw attention to a new 8 pm timeslot for Raw.

8. The Pipebomb

CM Punk

Heading into Money In The Bank in 2011 John Cena was the WWE Champion and his number one contender was the leader of The New Nexus, CM Punk.

Punk had already let it be known that his WWE contract expired on the same day as Money In The Bank and he fully intended to leave the company as WWE Champion. So far, so straightforward, a high-stakes game with a believable challenger but John Cena wasn’t called ‘Big Match John’ for no reason.

And then after costing Cena a Tables Match against R-Truth in the main event of Raw on June 27th, CM Punk turned the storyline and a wrestling industry that wasn’t exactly on fire with one promo as he sat cross-legged at the top of the ramp wearing a Stone Cold Steve Austin shirt.

Breaking every rule fans think they know WWE has, Punk mentioned people who didn’t work at the company at the time such as Paul Heyman, Brock Lesnar, and Hulk Hogan, he mentioned other wrestling promotions such as Ring Of Honor, and he even stared right down the barrel of the lens as he broke the fourth wall with a “hey Colt Cabana, how you doing?”

The Pipebomb led to one of the most memorable title wins of all time as CM Punk captured the title in front of a rabid hometown crowd in Chicago at Money In The Bank, kissing Vince McMahon goodbye as he seemingly left the company – three years before he’d do so for a lot longer.

7. The Radicalz Arrive

The Radicalz WWE

The Monday Night Wars, must-see television, wrestlers defecting, it was no doubt an exciting time to be a wrestling fan. By 2000, however, WWE had re-emerged as the kingpin of the industry with WCW’s decline gathering pace as it eventually went out of business.

Sean Waltman, Chris Jericho, Lex Luger, Rick Rude, Bret Hart, Jeff Jarrett, Scott Hall, Kevin Nash, and Paul Wight were among the stars who had made the jump one way or the other between WCW and WWE during this time. But on the 31st of January 2000, four WCW stars made the jump across the wrestling divide en masse and debuted on Monday Night Raw.

As Raw got underway with a tag team match between the New Age Outlaws and Al Snow & Steve Blackman, Eddie Guerrero, Dean Malenko, Chris Benoit, and Perry Saturn without warning all made their way to ringside seats to get the best view in the house.

After Road Dogg was thrown into the four men who JR referred to several times as “radical” on commentary, they chose to pounce, laying out the Outlaws before walking up the ramp seemingly as the newest members of the WWE roster in what was possibly the final shocking defection during the Monday Night Wars.

6. “Good God Almighty, They’ve Killed Him!”

Many a VHS tape has been rewound to near disintegration of two particular moments from the 1998 King Of The Ring event with the first of those even more shocking than the second.

The Undertaker had been besieged by Mick Foley since the Hardcore Legend made his WWE debut on the night after WrestleMania 12 back in 1996. As the summer of 1998 began to heat up the two men were on a collision course once again. This time a Boiler Room or a graveside wouldn’t be enough to settle their differences, this time The Undertaker and Mankind were set to face off inside Hell In A Cell.

This moment took place, however, before that encounter could take place inside the demonic structure as Mankind began proceedings by climbing to the top of the Cell. The Undertaker soon joined him and before long The Deadman launched Mick Foley off the Cell and into immortality as a whole new level of danger and destruction was introduced into the then-World Wrestling Federation.

5. “You Know Who I Am, But You Don’t Know Why I’m Here…”

On the first two-hour edition of WCW Monday Nitro, the wrestling world was changed forever while The Mauler wrestled Steve Doll in the ring.

It was neither of those men who made the headlines however as the late, great Scott Hall made his first WCW appearance since leaving the World Wrestling Federation. Hall entered the ring before cutting a promo to shocked silence from the crowd where he referenced WWE’s parody characters Billionaire Ted, The Nacho Man, and Scheme Gene before telling the “Ken Doll lookalike” Eric Bischoff that he had a challenge for him.

Hall returned at the end of the broadcast to make his challenge, telling Bischoff directly to find three opponents that would fight for WWE because “we are taking over.”

With WCW not naming Hall on its television show for several weeks or his soon-to-be partner Kevin Nash when he also joined the company and the vagueness surrounding the “we” in question that was taking over, WCW found themselves on the wrong end of a lawsuit by WWE. The suit was eventually settled in 2000 with the condition that if WCW was ever put up for sale WWE would have first refusal to buy the company – more on that later.

But first, Hall and Nash’s foray into WCW led to a six-man tag team match between themselves and a mystery partner to face the WCW team of Sting, ‘Macho Man’ Randy Savage, and Lex Luger at 1996’s Bash At The Beach. As it turned out the partner of Hall and Nash was even more shocking than Scott Hall showing up in WCW in the first place…

4. Hulk Hogan Goes Hollywood

Hollywood Hulk Hogan

Since 1983 Hulkamania had run wild, first in the World Wrestling Federation where Hulk Hogan captured the WWF Championship several times and had memorable feuds with the likes of Randy Savage, Ultimate Warrior, and Andre The Giant.

1n 1994 Hogan took his red and yellow talents to World Championship Wrestling and continued where he left off, winning fans and championships as wrestling’s perennial good guy.

But as Hulk Hogan was realising and the rest of the wrestling world was about to find out, the times they were-a changing and after the capture of Scott Hall and Kevin Nash, WCW was a very different beast altogether. After Hall had made his challenge to Eric Bischoff for a six-man tag team match and introduced Kevin Nash into the company, all wrestling fans wanted to know was who’s the third man for The Outsiders’ team?

Much speculation has been had on this subject over the years but once Hulk Hogan let it be known to Eric Bischoff that he might be interested in becoming a villain and joining Hall and Nash then he was the front runner for the role, despite another WCW icon originally agreeing to do it if Hogan changed his mind.

At Bash At The Beach in 1996, Hall and Nash began their match as a pair with Hogan only emerging later in the night seemingly to confront the two interlopers. As Bobby ‘The Brain’ Heenan wondered aloud whose side The Hulkster was on, WCW’s fans’ worst fears soon became realised as Hogan turned his back on the company and joined Hall and Nash.

Turning in the red and yellow for black and white, Hogan helped revitalise the entire wrestling world once again as he, Hall, and Nash injected their own lethal dose of poison into WCW as the New World Order.

3. Vince McMahon Buys World Championship Wrestling

Vince McMahon Shane McMahon Buys World Championship Wrestling

Now back to that little innocuous clause in the lawsuit settlement between WWE and WCW. Well, in 2001 World Championship Wrestling found itself out of time and at the end of the line. Up for sale, Eric Bischoff believed he had found the investment to take full control of the company he once ran but when TBS cancelled WCW’s TV timeslots, that investment was gone and there was only one person left ready to buy the ailing promotion.

On the second last edition of WCW Nitro the writing appeared to be on the wall as a forlorn Eric Bischoff appeared via telephone to warn everyone that the Panama City Nitro the following week could be the last wrestling show on the Turner Networks before all but confirming that fact as he made the event a Night Of Champions with every title on the line.

That prophecy was fulfilled with WCW’s final Nitro in Panama City airing on a special simulcast with WWE’s Monday Night Raw where WWE Chairman Vince McMahon told the world that he was the man who had purchased WCW, leaving himself standing all alone atop wrestling’s mountain.

An emotional Nitro that saw Booker T capture the World Championship that he brought to WWE was capped off with one final match in the company between Sting and Ric Flair with the old foes embracing in the ring afterward.

On Raw, Vince McMahon mocked his new plaything, firing Jeff Jarrett on live television and telling the world he wanted Ted Turner himself to come to WrestleMania 17 the following week to sign the contract. Unfortunately for McMahon, his hubris proved to be his downfall as someone else – at least in storyline – had beaten him to signing his name on the dotted line.

Shane McMahon showed up in Panama City to tell his father that the name on the contract did read McMahon but it read Shane McMahon. No matter which McMahon owned it, the reality was WCW was out of business, and to date, WWE has never yet faced the level of competition that the company gave it.

2. The Streak Is Over

Brock Lesnar Beats Undertaker WrestleMania 30

How can one wrestler losing a wrestling match possibly be more shocking than Vince McMahon ending the Monday Night Wars by buying WCW? The answer to that is very simple, the wrestler is The Undertaker and the match ended his two-decade-long undefeated streak at WrestleMania.

The Streak began at WrestleMania 7 in 1991 when The Undertaker defeated Jimmy Snuka in a forgettable match. Over the following years, The Deadman defeated the likes of Jake Roberts, Giant Gonzalez, King Kong Bundy, Diesel, Sycho Sid, Kane, Mark Henry, Big Show, A-Train, Edge, Randy Orton, Big Boss Man, Edge, CM Punk, Ric Flair, Batista, Shawn Michaels and Triple H without racking up a single loss at WrestleMania to his name.

It wasn’t until The Undertaker squared off with Randy Orton at WrestleMania 21 that The Streak became part of a storyline in WWE. At that point, the 2022 WWE Hall Of Famer was 12-0 at The Show Of Shows and the young Legend Killer felt like he was the man to finally give Undertaker a blemish on his WrestleMania record but it was not to be.

The Streak grew stronger as The Undertaker racked up wins and eventually The Phenom’s matches on The Grandest Stage Of Them All were as big as any WWE Championship match or main event.

Heading into WrestleMania 30, The Streak sat at 21-0 but The Undertaker was facing one of his stiffest tests at the event yet in the form of Brock Lesnar. Lesnar dominated the match but in typical Deadman spirit, The Undertaker simply would not die. After three F-5s however, Brock Lesnar pinned The Undertaker with the closing bell of the match being met with thunderous silence from the packed Mercedes-Benz Superdome crowd.

The unthinkable had finally happened, The Undertaker had lost at WrestleMania, and The Conqueror Brock Lesnar was born.

1. Montreal Screwjob

Bret Hart Vince McMahon

The most discussed thing in all of wrestling since that fateful night in November 1997 is without a doubt what came to be known as the Montreal Screwjob.

Books have been written, documentaries made, podcasts have been recorded all rehashing and revising the events that led up to and proceeded what took place at Survivor Series 1997.

For the casual observer, Bret Hart was set to defend his WWF Championship against Shawn Michaels in the main event of Survivor Series. Emanating from Hart’s native Canada, the crowd for the show was firmly behind him while they spewed venom at his opponent and degenerate Shawn Michaels. One hero, one villain, and a world title, wrestling 101, but the reality was anything but straightforward.

At the time Hart and Michaels loathed each other, a competitive rivalry turned personal – and physical – following repeated incidents and perceived disrespect. After Michaels had told Hart that he’d refuse to lose to him, Hart decided to follow suit, asking not to lose his title to Michaels in Canada.

There was one more elephant in the room to add to the powderkeg and that was Bret Hart was heading to WCW after Survivor Series – if the Hitman is to be believed, very much against his wishes.

A champion refusing to lose, a prima donna challenger, a competitor waiting with a fat chequebook and open arms, all that was needed was a spark to set the whole thing off.

According to a Dark Side Of The Ring episode on the ordeal, that spark came when Jim Cornette suggested in a booking meeting to Vince McMahon that they “take” the title off of Hart. Cornette maintains suggestions of how to do something like that were discussed but by the end of the conversation he believed McMahon had eschewed the idea.

That was until Jim Cornette witnessed, like the rest of the watching world did, Shawn Michaels put Bret Hart in his own Sharpshooter during their match only for referee Earl Hebner and Vince McMahon to both call for the bell, signalling HBK’s victory despite the fact Hart clearly hadn’t submitted.

Bret Hart destroyed the ringside area as his home country crowd showed their support while they hissed with venom at McMahon. Hart spat in the WWE Chairman’s face from the ring, going one better backstage when The Hitman excellently executed a punch that blackened McMahon’s eye.

For Vince McMahon, a new on-screen character was born that took his company to new heights feuding with the new apple of his eye Stone Cold Steve Austin. For months after the events of Montreal Shawn Michaels wrestled his last match for 4 years while Hart’s career in WCW never looked like approaching the heights it did in WWE before it was cruelly ended by an errant kick from Goldberg.