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Most Shocking WWE Moments Ever

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On the back of John Cena finally turning heel as he sold his soul to The Rock at Elimination Chamber, just what are the most shocking moments in WWE history?

Cody Rhodes was offered the chance to have everything handed to him by The Rock but The Final Boss had a price; Rhodes’ soul.

At Elimination Chamber Cody Rhodes gave The Rock his answer as he told him “Go f*ck yourself” but if you thought that was shocking then you better sit down for what happened next.

John Cena won the Elimination Chamber match to earn his WWE Title shot at WrestleMania 41 and he seemed thrilled that Rhodes stood up for himself, but that wasn’t best for business. Cena and The Rock were in cahoots and Cena nailed Rhodes below the belt before bloodying the champion with a Rolex and the WWE Title belt.

While there are sadly many tragic and shocking moments outside the ring, we’ve stuck with the stories that are part of the show and that have played out on screen.

But where does John Cena turning heel in his final year as a WWE Superstar truly rank in WWE’s most shocking moments?

Pillman’s Got A Gun!

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 a 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.

The Radicalz Arrive In 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.

“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.

Hell Freezes Over For CM Punk

In January 2014, there was not a lot of good feeling surrounding WWE. The Royal Rumble had been brutally dumped on by fans who wanted nothing else but a Daniel Bryan win. Imagine their upset when he wasn’t even in the match. Instead, it was Batista who won the Rumble but no one was happy to the extent that the feeling was turning into something the company feared more than anything else, apathy.

One man who was anything but apathetic about his own role in the ongoing mess was CM Punk. Punk walked out of the company and ended up being sent his release papers on his wedding day. Something he was told was merely a coincidence.

Punk went public with his unhappiness leading to legal action, friendships collapsing and a general feeling that Punk would never be back. But in 2023 he was, thanks in part at least to his even greater unhappiness in another wrestling promotion.

CM Punk joined AEW in 2021 but his two-year spell in Tony Khan’s company was snakebit. At All Out 2022, CM Punk won the AEW World Title and then all hell broke loose. Punk was injured in that match putting him out of action for months but he still had enough in him to let rip on the company and many of its stars at a post-show press conference before getting involved in a fight backstage with The Young Bucks.

Punk returned to AEW in the summer of 2023, but it wasn’t long until things went wrong again. CM Punk was fired by AEW after an altercation with Jack Perry at All In London and enough was finally deemed to be enough.

At Survivor Series 2023, just a few short weeks after that firing, CM Punk returned to WWE at Survivor Series in his home city of Chicago to a hero’s welcome. Punk shared a photo with Triple H as they apparently buried the hatchet that they previously only buried in each other’s backs. All is well again between CM Punk and WWE and fans of his will be hoping that lasts.

John Cena Turns Heel

John Cena was recruited by Kurt Angle for his five-man team at Survivor Series in 2003 and that marked Cena’s official return to babyface status in WWE and started him on his road to wrestling immortality.

Not long after Cena won the WWE Title at WrestleMania 21, fans were already starting to divide over Cena. The boos got louder as the older, male audience rallied against “Super Cena” who seemed able to win no matter the odds. While in years gone by WWE might have reacted to these jeers and turned the star heel, they never did with Cena perhaps buoyed by his relentless popularity with kids and ability to sell t-shirts of any colour.

Many rumoured plans were made to turn John Cena heel but the trigger was never pulled. But if wrestling has taught you anything, then you know to never say never.

At Elimination Chamber, John Cena booked his WWE Title match at WrestleMania 41 against Cody Rhodes. The signs were there for people to see, Cena declared his entry to the match rather than earn it like everyone else and he was truly hiding in plain sight when he explained that winning his 17th world title was “best for business.”

TKO board member The Rock wanted Cody Rhodes’ soul and seemingly sought to make him The Rock’s own corporate WWE Champion but Rhodes is his own man and wanted nothing to do with The Final Boss. Perhaps taking a leaf out of Triple H’s book, The Rock had a plan b as he gave John Cena the signal and John Cena nailed Rhodes below the belt before bloodying him with his own WWE Title belt.

The crowd in Toronto were stunned into near silence, unable to comprehend that the long-wanted John Cena heel turn nobody thought would happen finally had in the last year of his career.

Vince 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 afterwards.

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 that WCW was out of business, and to date, WWE has never yet faced the level of competition that the company gave it.

The Streak Is Over

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.

Montreal Screwjob

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.