15 Cringeworthy Wrestling Moments You Can't Help But Watch Over Again

You never look away from a car wreck and you can't look away from these... 15 Cringeworthy Wrestling Moments You Can't Help But Watch Over Again.

Never let it be said that wrestling doesn’t take risks. Unlike a traditional television series, there is no off-season when it comes to professional wrestling which means that bookers have to get creative in order to keep their product fresh and their fans guessing. It’s because of this we have storylines like a cajun cult leader with unexplained supernatural powers taking on the king of demons, not to mention an evil band of male cheerleaders, an undead demonic wizard and the head of the WWE wrestling a match against God. As you can probably imagine, these risks can lead to unimaginable highs as well as the lowest of lows, creating moments that are remembered for their exhilarating storytelling or downright cringeworthyness.

The WWE in particular is known for pushing the envelope, creating memorable moments that both shocked and disturbed viewers. Who could forget the time Triple H filmed himself sneaking into a casket and simulating some carnal acts on a dead woman’s body? Or the time when Mae Young gave birth to a human hand? Well those segments could be considered highlight reel worthy compared to some of wrestling’s more humiliating misfires, creating moments so cringeworthy, that you not only feel embarrassed for the people in the ring but at yourself for being a fan.

The following list chronicles some of the most cringeworthy moments in the history of professional wrestling. From gimmicks that sorely missed the mark, to segments that fell flat with fans to botches that hurt a performer’s pride more than their bodies, these moments will surely make you feel some serious second-hand embarrassment.

15 Bayley: This Is Your Life


If any WWE Superstar’s career has embodied the phrase “cringeworthy,” this year, it’s Bayley. After winning her first Women’s Championship in February, the beloved Hugger has been put through a series of head-scratching booking decisions that have killed her momentum, leading to her being booed out of the building while making a heartfelt injury announcement in August. However, the crown jewel of “Bayley Gets Buried 2017” has got to be the Bayley This Is Your Life segment from earlier this year. Modelled after the classic 1999 segment featuring The Rock and Mankind, the WWE surely felt they had a winner on their hands, setting the stage for Bayley’s anticipated rematch against new champ Alexa Bliss.

However, what ensued was an 11+ minute segment that was such a spectacular trainwreck, not even Little Miss Bliss’s superior promo abilities could save it. The set-up was simple, Bliss sets out to prove Bayley isn’t woman enough to take her title back by painting her as a naive little girl, showing off her doll collection and even interviewing her teacher, first boyfriend and childhood best friend to humiliate her. However, between the student film-level acting, pathetic punchlines and Tarantino-length runtime, by the end of the seemingly endless segment, you could barely hear the performers over the vociferous booing from those in attendance. The segment is not only considered the worst wrestling moment of 2017, but the first nail in the coffin that is Bayley’s babyface run.

14 Jeff Hardy Shows Up In NO Shape To Compete At Victory Road


It’s no secret that Jeff Hardy has dabbled in certain mood-altering substances throughout his illustrious wrestling career. The fearless high flyer has made a name for himself by putting his body through an insurmountable amount of punishment for the entertainment of fans worldwide, leaping off of ladders, putting himself through tables and falling off of just about anything with a ledge. However, this death-defying style takes quite the toll on one’s body and it wasn’t long before Hardy became addicted to the muscle-relaxing drug Soma.

It’s this that lead to one of the most cringeworthy moments in the former WWE Champion’s career, showing up high to his TNA World Championship match against Sting at the pay-per-view, Victory Road. As the innovative grappler stumbled and drifted to the ring with a glassy-eyed expression, it was clear that something wasn’t right, a fact made even more evident when general manager Eric Bischoff came out to call off the match. The two would wrestle for just 90 seconds before Sting eked out the win, tasked with ending the bout as quickly as possible as Hardy was deemed too inebriated to compete. Thankfully Hardy is now clean and sober, having made his Cinderella-story return to the business just a year later.

13 Stephanie McMahon’s 9/11 Tribute


9/11 remains one of the most devastating attacks in the history of the United States. It impacted countless lives, killed almost 3,000 people and changed a nation forever. So of course, when the WWE aired their 9/11 tribute show on SmackDown just two days after the catastrophic event, emotions were running high. Throughout the show, the sports entertainment giant aired a series of video packages filled with messages of hope and expressions of condolence from the WWE roster. However, it’s Stephanie McMahon’s message that stood out from the rest as she equated the terror attacks to the steroid trial her family had endured just years before.

“A few years ago, some people tried to destroy my family. They attacked my father’s reputation, they attacked my mother’s reputation and they attacked the World Wrestling Federation (as it was known at the time). They tried to rip us apart but all they did was make my family stronger. And that’s exactly how America feels right now.”

The speech was rightfully criticized for being out of touch and misguided in trying to make one of the most impactful events in American history about the McMahon family dynasty. It’s something the WWE is likely aware of as the Billion Dollar Princess’s address is one of the few conspicuously absent from the WWE’s YouTube channel.

12 Sufferin Succotash Roman Reigns


In today’s PG Era of the WWE, there is only so much you’re allowed to say when taunting your opponent in a promo. While back in the day you could tell them to “Suck it!” like DX or flip them off like Stone Cold Steve Austin, today’s superstars have to find unique ways to cut down their adversaries, using watered down, family friendly language. It’s a challenge that some have risen to the occasion for, delivering cutting, blistering promos without ever triggering a censor, and then, there’s Roman Reigns.

The Big Dog of the WWE has struggled to hold his own during verbal showdowns with the WWE roster, a fact he more than proved during a 2015 promo against Seth Rollins on Smackdown. “You are full of something else,” Reigns informed the Kingslayer, evoking a PG-13 rated phrase that has gone largely unsaid on WWE programming over the past few years. However, what he followed that up with is far more likely to cause second-hand embarrassment than it is pearl-clutching. “You are a snivelling, little suck-up, sellout full of suffering succotash, son!” If you want to intimidate your opponent, it’s probably best not to crib your insults from the Looney Tunes.

11 Natalya Can’t Stop Farting


Over the years, the WWE has inflicted a host of humiliating gimmicks on its roster and the women are no different. There was that terrible “Piggy James” angle where the women of SmackDown body-shamed a perfectly fit Mickie James, calling her fat until she cried. Then there was, well, just about anything involving Jillian Hall, but more specifically that time she was made to wear a giant, disgusting mole on her face that was eventually eaten by the Boogeyman. However, the award for most embarrassing gimmick has to go to Natalya who, at someone’s stroke of genius, was made to fart uncontrollably during her matches.

For weeks, the lone female graduate of the Hart Dungeon’s storyline was that she couldn’t stop farting. Passing gas in backstage segments, during interviews and yes, during matches, referees sometimes even stopping what they were doing to feign gagging. Booker T would explain during commentary for one of these matches that Natalya was simply so committed to her fitness regime and was consuming so many protein shakes a day that it was having an adverse effect. We’re just glad that the now one-time SmackDown Women’s Champion is being shown a little more respect.

10 The Fingerpoke Of Doom


There are few factions more integral to the success of WCW in the mid-90s than the nWo. Consisting of Kevin Nash, Scott Hall and Hulk Hogan, the villainous group skyrocketed the Ted Turner-owned promotion into ratings success and cultural prominence, overtaking the WWE for quite some time. However, much like any wrestling promotion, things have to change in order for storylines to stay fresh. Beginning to get stale, the nWo was split up into several factions with Nash leading the Wolfpack nWo (the good guys) and Hogan leading the Hollywood faction (the bad guys).

The two had been feuding for almost a year when a match was booked for Nash’s WCW World Heavyweight Championship as the main event of a January 1999 episode of Nitro. However, as they stood face to face in the center of the ring, Hogan would do something that would markedly change WCW’s future. He would poke Nash in the chest, causing Nash to dramatically throw himself into the mat and allow the wrestling icon to pin him for his title. While it was meant to reveal that the feuding factions had reunited, fans revolted and the segment is often pinpointed as WCW’s “jumping the shark” moment, signifying the beginning of the end for the promotion.

9 The House Of Horrors Match


To be honest, there’s very little about Bray Wyatt that isn’t cringeworthy these days. The dreadlock-sporting supernatural cult leader was one of the WWE’s most exciting performers at the beginning of the year, his winning of the WWE Championship at Elimination Chamber a sign of hope for the future of the SmackDown title scene, and then House of Horrors happened. At the time, Wyatt was feuding with his former disciple Randy Orton, a program that was one of the most anticipated in the lead up to WrestleMania. However, when the match resulted in Wyatt protecting a series of creepy crawlies onto the mat before being flattened by Orton in 10 minutes, much of the luster was taken from the former fan favorite.

So when Wyatt challenged Orton to a rematch in what would be the first House of Horrors Match, many wondered what that could possibly entail. Rumblings suggested the match was doomed before it even began, not even the WWE knowing what said match was going to be and if that is true, it was certainly evident in the final product. What resulted was a pre-taped match inside a rundown house that had the production value of a B-movie on the SyFy channel. If you wanted to see Wyatt and Orton fight in a room full of creepy dolls before having an old refrigerator dumped on one of them, you were in luck. For the rest of us however, this is a match that’s best forgotten.

8 The Shockmaster Fumbles His Debut


Consider this the worst (or best) debut in the history of professional wrestling. The year was 1993 and Nature Boy Ric Flair had made a grand announcement in the leadup to WCW’s upcoming pay-per-view Clash of Champions. On his “talkshow” Flair For Gold, he would unveil the mysterious new partner of Sting and the British Bulldog who would aid them in their WarGames match against Sid, Vader and Harlem Heat. It’s a partner who was shrouded in secrecy, Sting claiming that he would “shock the world,” and that he did, just not in the way anyone expected.

The plan was to introduce WCW to their newest monster, The Shockmaster, a big, hulking wall of a man who was intended to strike terror into the hearts of men, women and children everywhere. The plan was for him to burst through the wall during the segment, demonstrating his monstrous abilities. What happened however, was anything but terrifying. The Shockmaster, clad in a furry vest and bedazzled Stormtrooper helmet, would trip as he powered through the wall, falling onto his face and knocking his helmet off with it. While he would put the helmet back on and power through the segment, it was too late, the allure was gone, his character was already a joke.

7 That Jackie Gayda Match


As any wrestler can tell you, you’re only as good as the person you’re up against. No matter how good you are, wrestling is a dance and if your partner can’t pull their weight, you’re dead in the water. It’s a lesson Bradshaw and Trish Stratus learned the hard way when they teamed up to take on Christopher Nowinski and the WWE’s newest recruit, Tough Enough winner, Jackie Gayda in a tag match on Monday Night Raw.

Despite being a celebrated performer and one of the most decorated women in WWE history, Stratus was unable to overcome Gayda’s inexperience, resulting in what’s been dubbed the worst match in WWE history. While each of the participants valiantly fought to keep the match on track, there were few moves that Gayda didn’t botch leading to a messy and frankly embarrassing bout to watch. “Mercifully it’s over,” announcer Jim Ross would remark as Stratus and Bradshaw walked away victorious, quite possibly the truest statement ever spoken in professional wrestling.

6 Vince McMahon Says The N-Word


There are offensive moments in professional wrestling that can be looked back on and forgiven due to the cultural climate of the time. This isn’t one of those moments. Back in 2005, John Cena was riding high as the WWE’s hottest new main eventer, having become a fan favorite thanks to his Doctor of Thuganomics gimmick that essentially saw him become the WWE’s answer to Vanilla Ice. It’s a gimmick that WWE boss Vince McMahon decided to play off in a backstage segment at that year’s Survivor Series, strolling up to Cena and asking, “What’s good in the hood?” prior to his WWE Championship match against Kurt Angle.

When Cena said he was good, McMahon would follow it up with, “Well keep it up, my…” calling the WWE champ the N-word. He’d then stroll passed Booker T and his wife, Sharmell, their mouths agape as Booker would end the segment by seething, “Tell me, he did not just say that!” It’s a moment that drew criticism at the time and has only aged worse since, especially considering the company would sever ties with Hulk Hogan ten years later after leaked tapes revealed Hogan using the word among other racist hate speech.

5 The Actual Worst Match In TNA History


When Sharmell faced Jenna Morasca at Victory Road 2009, putting on what many considered to be the worst match in the company’s history, it was easy to see why the bout was such a failure. Neither was a trained wrestler, Sharmell best known for being married to a veteran performer while Morasca is a reality personality, famous for winning her season of Survivor. So when two trained wrestlers stepped into the ring at TNA’s One Night Only: Knockouts Knockdown in 2016 to put on the actual worst match in the company’s history, the result was far less excusable.

At the event, which saw their women’s division battling to be named “Queen of the Knockouts,” Shelly Martinez (known to WWE fans as Ariel) and Rebel put on a match so sloppy and poorly executed, it’s amazing that either had any prior experience at all, nevermind years of it. For 10 minutes the two threw each other around the ring, botching just about every move they attempted for a match so bad that it was named Wrestling Observer’s Worst Match of 2016 across all wrestling promotions. After all, when your match is best remembered for one of your performers exclaiming that she hurt a certain explicit body part, it’s probably not destined to go into any Hall of Fames.

4 Rosie O’Donnell vs. Donald Trump


It’s easy to forget now that Donald Trump is leader of the free world and embattled in increasingly ridiculous scandals on a seemingly daily basis but there was a time when the future President was an active member of the WWE Universe. Most notably, he participated in a Hair vs. Hair Match at WrestleMania 23 (represented by Bobby Lashley against his good friend Vince McMahon (represented by Umaga) that ultimately saw McMahon lose his famous locks. However, in 2007, during the height of the Donald Trump vs. Rosie O’Donnell media feud, the WWE had two stand-ins settle their beef during a match on Monday Night Raw.

From the terrible lookalikes to the offensive pot shots regarding O’Donnell’s weight, to the fact that neither were actually wrestlers, it was an embarrassing display all around that of course, ultimately saw Trump come out on top thanks to a “hairbutt.” This wouldn’t be the last time the company pulled off such an obvious publicity stunt either, having Hillary Clinton and Barrack Obama lookalikes face off during the 2008 Presidential election.

3 The Fake Diesel And Razor Ramon


Back in the early 90s, past the glory days of Hulkamania but before the cultural resurgence the Attitude Era would bring, two wrestlers can be credited with holding the WWE fanbase together; Kevin Nash and Scott Hall known at the time for their characters Diesel and Razor Ramon. So when the two jumped ship in early 1996 to join their competitors WCW, the WWE had quite the decision to make on how they were going to fill the void. It’s a question that was seemingly answered in September of that year when Jim Ross made the bold announcement that Diesel and Razor Ramon would once again be joining the WWE ranks, making their return to Monday Night Raw in the coming weeks.

While Nash and Hall were currently two of WCW’s biggest draws, in this pre-Internet era, with little behind-the-scenes intel to go on, many took this announcement to mean that the two had been re-signed to the WWE. So imagine their disappointment when the debuting “Diesel and Razor Ramon” turned out to be nothing but two imposters dressed like the wrestlers. Having retained the rights to the characters, the wrestling giant decided that replicating their success was as easy as swapping in two new bodies into their already iconic gear, a move we don’t have to tell you did not fly with fans. And while Fake Diesel would find great success with the company later as Kane, it still remains one of their most baffling decisions.

2 TNA’s Electrified Steel Cage Match

The excitement of any gimmick match is that it adds a sense of danger to a matchup, forcing its competitors to get creative in how they’re going to overcome the obstacle while hopefully raising the heart rate of viewers in the process, making you question whether either participant is going to leave the bout unscathed. However, that’s a lot easier to accomplish when the danger is real. It’s a lesson TNA learned the hard way when they put on the disaster that was the Electrified Steel Cage Match at their Lockdown pay-per-view in 2007. Pitting Team 3D (known to WWE audiences as The Dudley Boyz) against LAX, it’s remembered as one of TNA’s most embarrassing blunders and that’s saying something.

The concept of the match was simple, the teams would wrestle in a cage that would intermittently emit a charge of electricity, shocking those inside. The problem was, the wrestlers weren’t actually going to be electrocuted. Instead, the lights would simply flash as the humming sound of electricity was broadcast over the PA, forcing those involved to drop to the ground and seize, pretending to be electrocuted. While there was talk of sparks being produced by the cage, they never materialized leading to a match that was not only embarrassing to watch for all involved but did a serious disservice to kayfabe, having to see some of the toughest wrestlers around essentially playing “stop, drop and roll” every few minutes during the match.

1 David Arquette Wins WCW Championship

via Pro Wrestling Illustrated

What’s the best way to ensure that the credibility of your #1 championship is destroyed beyond recognition? Have it won by a Hollywood actor with no previous wrestling training of course. The year was 2000 and already on the brink of collapse, WCW decided to join forces with sister company, Warner Brothers to produce the movie Ready To Rumble, a wrestling comedy starring David Arquette. In an effort to promote the movie, the company decided to replicate the finale of the film which saw Arquette competing in a triple cage match, by holding a similar match at that year’s Slamboree pay-per-view.

In an attempt to no-doubt leverage that “star power” into press, producers had Arquette appear on the go-home episode of Thunder where he was scheduled to compete in a tag team match with Diamond Dallas Page for DDP’s WCW World Heavyweight Championship. How do you win a singles championship in a tag team match when you’re teamed with said champion? That’s a good question, one that wasn’t answered by the time Arquette pinned Eric Bischoff to become the new WCW Champion. His reign would last just four days, ended by Jeff Jarrett at Slamboree and for Arquette’s part, he acknowledges that his title reign was a joke, having donated his earnings from the reign to the families of Owen Hart, Brian Pillman and Droz. However, it’s still singled out as a primary reason for WCW’s demise and one of the worst booking decisions ever.

Give TheSportster a Thumbs up!

Looking for an AD FREE EXPERIENCE on TheSportster?

Get Your Free Access Now!

More in Wrestling

15 Cringeworthy Wrestling Moments You Can't Help But Watch Over Again