The 23 Most Cringe Wrestlemania Moments Of All Time

Let's look back at the most uncomfortable moments on WWE's "Grandest Stage of Them All."

Wrestlemania is often considered to be the biggest annual event in the entirety of professional wrestling, as WWE captures headlines and orchestrates dream matches for loyal viewers and lapsed fans alike.

WWE / Via media.giphy.com

But for a show that emphasizes every memorable match and sensational spectacle, Wrestlemania has hosted a treasure trove of unintentionally strange, uncomfortable, and cringey moments that live on in infamy. With Wrestlemania 38 right around the corner, I've tracked down more than 20 of those moments so you, too, can revel in some sports entertainment schadenfreude.

1. Brock Lesnar's Shooting Star Botch (Wrestlemania 19)

WWE / Via YouTube

When Brock Lesnar debuted in the WWE in the early '00s, the future UFC star and multi-time WWE champion had the reputation of being an athlete unlike anything the company had scene. With the build of a super heavyweight and the agility of a cruiserweight, Lesnar would wow audiences during his days in developmental with his use of a Shooting Star Press, a standing backflip from the top rope that was risky but incredibly impressive. 

By the time he was ready to make his Wrestlemania debut in a championship match with former Olympic gold medalist Kurt Angle, Lesnar decided to break out the move for the first time in the big leagues, only for him to fail to execute the rotation and nearly land directly on his head and neck. Brock Lesnar narrowly avoided a broken neck — or worse — but this moment remains one of the scariest Wrestlemania fails of all time.

Where to Watch: You can watch this clip on WWE's YouTube Channel (skip to 20:16).

2. Mickey Rourke Drops Out and Knocks Out (Wrestlemania 25)

Matt Roberts / ZUMA Press / Courtesy Alamy

As Darren Aronofsky's The Wrestler became a critical and commercial hit, WWE decided to embrace the project and courted star Mickey Rourke to have a wrestling match with Chris Jericho. However, Rourke soon became worried by an in-storyline confrontation between the two on Larry King Live, fearing that the acclaimed wrestler would actually injure him in the ring. 

With Rourke dropping out of the match mere weeks before the event, Jericho would instead wrestle the legendary Roddy Piper, alleged murderer Jimmy Snuka, and the legitimately amazing-for-his-age Ricky Steamboat at Wrestlemania, with a clearly apprehensive and seemingly uneasy Rourke shuffling to the ring to "punch out" Jericho after the match to avenge the fallen legends.

Where to Watch: You can watch this clip on WWE's YouTube Channel.

3. Molly Holly's Shaved to Save Her Match (Wrestlemania 20)

WWE / Via YouTube

Women's wrestling was essentially at a devastatingly low point in the WWE by the time Wrestlemania 20 rolled around, as the only other women's match on the card was a "Playboy Evening Gown" match that served as an excuse to promote an upcoming Playboy spread and mercifully ended under three minutes. 

With the WWE Women's Championship about to be left off of the card entirely, WWE Hall of Famer Molly Holly went beyond the call of duty for the belt to be represented on the Grandest Stage of All, agreeing to have her head shaved in a "Belt vs. Hair" match. Holly and her opponent, Victoria, put on a solid five-minute match, but sadly followed with an extended head-shaving segment that was as degrading and uncomfortable as it sounds.

Where to Watch: You can watch this clip on WWE's YouTube Channel.

4. The Miller Lite Girls Bring Their Catfight IRL (Wrestlemania 19)

Andrea Renault / Globe Photos / ZUMAPRESS.com / Courtesy Alamy

In the weeks prior to Wrestlemania 19, America fell under the spell of an incredibly stupid Miller Lite Superbowl commercial depicting a pair of women engaged in a destructive, sexualized fight sequence. In classic WWE fashion, the promotion decided to recruit the actors Kitana Baker and Tanya Ballinger to tussle with their female performers at the biggest show of the year in the "Women's Catfight Challenge." 

As much energy as it could take to be angry about the misogyny and objectification on display, the segment is also just a sleazy and boring waste of time that probably worked to the detriment to both fans and talent.

Where to Watch: You can watch this clip on Peacock.

5. Rain Descends Upon Wrestlemania (Wrestlemania 37)

Luis Santana/Tampa Bay Times/ZUMA Wire/Alamy Live News

Excitement was at an all-time high at Wrestlemania 37 in Raymond James Stadium, WWE's first live event following the outbreak of the COVID-19 pandemic. With thousands of fans in attendance, the show was ready to kick off with an explosive WWE Championship match...but mother nature had other ideas, as a thunderstorm came down on the crowd mere minutes before the show was to begin. 

With no overhead cover on the stadium, the seemingly snakebit show was essentially stalled for nearly 15 super-cringey minutes, as WWE resorts to bad improv, time-wasting updates and re-airing video packages until the weather eventually let up enough to start the show.

Where to Watch: You can watch this clip on Peacock.

6. The Undertaker vs. Giant Gonzalez (Wrestlemania 9)

WWE / Via YouTube

While Wrestlemania has been the home to many hoss fights, none has been as lumbering and terrible as the battle between Giant Gonzalez and The Undertaker at Wrestlemania 9. A relative newcomer to pro wrestling, Giant Gonzalez appeared to have no idea what he was doing, and to make matters worse, was wearing his bizarre skin-tight suit that made him look like a shaved, nude cryptid. Now known as one of the worst matches in Wrestlemania history, The Undertaker later spoke ill of the bout, stating, "It was bad on so many levels."

Where to Watch: You can watch this clip on WWE's YouTube Channel.

7. Hogan Ruins Wrestlemania at the Superdome (Wrestlemania 30)

Matt Roberts/ZUMA Wire / Alamy Live News

Over the past several decades, Hulk Hogan's legacy has gone from one of the defining faces of professional wrestling to that of a relic of wrestling's past marred by a racist tirade uncovered from his sex tape in 2015. However, Hogan's mouth previously got him ridiculed one year prior at Wrestlemania 30 at the BMW Super Dome in New Orleans, in which the former WWE champion opened the show and immediately bungled the name of the arena, confusing it with the Pontiac Silverdome in Michigan. 

Met with a chorus of boos from the 75,000 fans in attendance, Hogan eventually corrected himself before getting ridiculed by his co-hosts to the introduction, "Stone Cold" Steve Austin and Dwayne "The Rock" Johnson.

Where to Watch: You can watch this clip on WWE's YouTube Channel.

8. Big Show Goes Sumo vs. Akebono (Wrestlemania 21)

J. Shearer / WireImage for BWR Public Relations / Getty Images

Some of Wrestlemania's most cringeworthy moments emerge from the company's decision to experiment on the Grandest Stage of Them All, from over-the-top gimmick matches to celebrity appearances. Sadly, at the center of most of these matches has been Paul Wight, aka The Big Show, who was set for a sumo exhibition at Wrestlemania 21 against iconic sumo wrestler Akebono Tano. 

The match was an uncomfortable and strange experience from top to bottom, and still has critics of the event scratching their heads more than 15 years later.

Where to Watch: You can watch this clip at WWE's YouTube Channel.

9. Mr. T and Roddy Piper Work Themselves Into a Shoot (Wrestlemania/Wrestlemania 2)

Adam Scull / PHOTOlink / MediaPunch / Courtesy Alamy

In wrestling lingo, all storyline action is known as a "work," while unscripted action (and, in some cases, violence) is known as a "shoot." Sometimes, when performers have real-life animosity, the lines between "work" and "shoot" blur, and that was the case when the WWE booked The A-Team star Mr. T against "Rowdy" Roddy Piper at the inaugural Wrestlemania, as Piper's perceived disrespect on the part of Mr. T inspired the former to go off script to incite and rough up the latter. 

This animosity bled over to their "re-match" at Wrestlemania 2, as the two would have a "worked" boxing match that remains a benchmark in wrestlecrap history.

Where to Watch: You can watch this clip at WWE's YouTube Channel.

10. The D-Generation X Band Slaughters “America the Beautiful” (Wrestlemania 14)

WWEMusic / BMI / youtube.com / Via YouTube

One of the rare clips from Wrestlemania history that has since been removed from WWE's released videos and library, this incredibly uncomfortable performance at Wrestlemania 14 shows the D-Generation X Band and lead singer Chris Warren presenting a rendition of "America the Beautiful" with a nu wave style. 

The audience immediately turns on the performers, nearly drowning out the music with a tidal wave of furious boos. WWE must have equally found the display disrespectful, erasing it from all digital releases of Wrestlemania 14, leaving it to online bootleggers to preserve its memory.

Where to Watch: You can listen to the clip above.

11. Bart Gunn vs. Butterbean (Wrestlemania 15)

WWE / Via YouTube

In the late 1990s, the WWE experimented with real boxing with their MMA/boxing competition "The Brawl for All," in which their wrestlers faced one another in real, unsanctioned fist fights. The event was an unmitigated disaster, as several wrestlers (and their reputations) were injured, but if anyone came out on top, frequent tag team wrestler Bart Gunn proved himself to a force to be reckoned with among his peers. 

Gunn's unplanned win was rewarded with a one-on-one boxing match with Eric "Butterbean" Esch, who knocked Gunn out in mere seconds in one of the more unnerving displays of real violence in WWE history and effectively ended his career in the promotion.

Where to Watch: You can watch this clip at WWE's YouTube Channel.

12. The Dance of the Funkasaurus (Wrestlemania 28)

WWE / Via Giphy

Without any context, here we go: Controversial wrestler Tyrus, previously known as Brodus Clay, was randomly rebranded as the Funkasaurus during his tenure at the WWE, given a pair of dancing valets known as the Funkadactyls, and bestowed with an over-the-top theme song "Somebody Call My Momma," which formerly belonged to a WCW wrestler named Ernest "The Cat" Miller. With no match on the Wrestlemania 28 card, Clay was saddled with a dance segment with a dancer in a "Momma" costume, dancing with the Funkadactyls for seemingly no reason. 

This surreal segment was allegedly on the chopping block at the pay-per-view until Clay's friend, John Cena, decided to browbeat WWE chairman Vince McMahon into keeping the bizarre and senseless number on the show in its entirety.

Where to Watch: You can watch this clip on Peacock.

13. The Battle of the Announcers (Wrestlemania 27)

Matt Roberts / ZUMAPRESS.com / Courtesy Alamy

Renowned for its sheer absurdity, the Michael Cole/Jerry Lawler feud at Wrestlemania 27 is notorious as one of the worst Wrestlemania angles of all time, a conflict between two broadcast colleagues that was parlayed into terrible, lifeless promos, lame-duck interpersonal drama, and an in-ring match that's sincerely among the worst of them. This cringey angle is perhaps only salvaged by the fact that it's so bad that it's been repurposed into some of the funnier online wrestling parodies on YouTube.

Where to Watch: You can watch this clip on Peacock.

14. The Wrestlemania That Almost Wasn't (Wrestlemania 36)

Luis Santana/Tampa Bay Times/ZUMA Wire/Alamy Live News

For the WWE, the show must go on, no matter the circumstances. In early 2020, Wrestlemania 36 seemed to be one of their biggest cards ever: Drew McIntyre would bring his comeback story to life with a headlining match against Brock Lesnar, Roman Reigns would go face to face with WWE Hall of Famer Goldberg, and the Undertaker would return to wrestle fan favorite AJ Styles, among many other bouts. 

Yet like the rest of the world, March 2020 would force WWE to flip its script, scrapping its intended major arena venue in favor of their secluded Performance Center location and reshaping a number of bouts, now in front of an audience of zero, on the fly. 

Within hours of the new Wrestlemania 36, the company's biggest star (and leukemia survivor), Roman Reigns, would drop out of the show, while big angles for The Undertaker, John Cena, and Rob Gronkowski were reworked outside of the ring entirely. 

At the end of the day, the decisions would work out in the end: The Cena/Fiend match displayed WWE at their creative best while Roman Reigns' absence would fuel a stellar heel turn that revitalized his career at Summerslam 2020. However, WWE's first empty-room pay-per-view still has a haunting, awkward quality about it, especially considering most of the world was still quarantined during this time.

Where to Watch: You can watch this clip on Peacock.

15. Mary Tyler Moore Does Not Care About Wrestlemania (Wrestlemania 6)

WWE / Via YouTube

Wrestlemania 6 is remembered for many reasons: the Ultimate Warrior's coronation as the company's newest top star, Andre the Giant's final televised WWE match, and an extremely controversial match between Roddy Piper and Bad News Brown (more on that later). But one thing best left forgotten is the impromptu interview with ringside guest (and sitcom stalwart) Mary Tyler Moore, whose off-guard, deer-in-headlights look is matched only by her utter indifference to wrestling as a whole, though she nicely compliments the spectacle and athleticism on display.

Where to Watch: You can watch this clip on WWE's YouTube Channel.

16. Brock Lesnar vs. Goldberg vs. The Crowd (Wrestlemania 20)

John Barrett/PHOTOlink / MediaPunch / Courtesy Alamy

By the time Wrestlemania 20 came to New York City, the word hit the street that both Goldberg and Brock Lesnar were exiting the company, as both had grown disillusioned with the organization and hoped to seek opportunities elsewhere. With a giant Wrestlemania send-off match planned and a freshly retired Stone Cold Steve Austin set as the special referee, no one could have planned for how weird and tumultuous this experience would become, with the crowd loudly and proudly turning on the match and its performers before it even began. 

Eventually, the first ever Goldberg/Lesnar match (which is terrible by all accounts) would end with Goldberg getting one last win before both performers were hit with Stone Cold Stunners in the most odd moment on a show that later featured ex-governor Jesse Ventura interviewing future president Donald Trump.

Where to Watch: You can watch this clip on WWE's YouTube Channel.

17. Hogan Ruins Wrestlemania at Caesars Palace (Wrestlemania 9)

WWE / Via YouTube

"Hogan must pose." According to Something to Wrestle With Bruce Prichard, this was WWE's mantra for booking Hulk Hogan during the 1980s, but by 1993, Hulkamania was clearly on the decline. As a result, WWE overbooked themselves into one of the cheesiest and worst endings to any Wrestlemania ever, when Hogan (donning an obvious yet never acknowledged eye injury) comes out following the truncated main event in which the evil Yokozuna defeated fan favorite Bret Hart. 

With a reluctant onscreen green light from a visibly annoyed Hart, Hulk Hogan enters the ring and defeats Yokozuna for the championship to a confused and underwhelming response from those in attendance. In one fall swoop, WWE not only undermined the burgeoning popularity of its top hero and top villain, but doubled down on the worn-out popularity of a talent that would be working for their top rival one year later, which feels all the more surreal when happening in daylight at Caesar's Palace.

Where to Watch: You can watch this clip on WWE's YouTube Channel.

18. John Cena on Bended Knee (Wrestlemania 33)

Stephen M. Dowell/Orlando Sentinel/TNS/Alamy Live News

Admittedly, this moment is way more cringey knowing what we know now, but Wrestlemania 33 in Orlando turned a spotlight into their most famous real-life couple, John Cena and Nikki Bella, whose relationship had been in the public eye throughout the latter's reality series, Total Bellas. After defeating The Miz and his wife, Maryse, in a tag team match, John Cena dropped to his knee, addressed Nikki by her IRL name, and popped the big question in front of the crowd and the millions watching at home. 

Under normal circumstances, this would have been a shining, romantic moment that paved the path for a happy ending... But one year later, Cena and Bella would call off their engagement less than a month before their wedding. But much like diamonds, this clip lives on forever to keep wrestling fans cringing time and time again.

Where to Watch: You can watch this clip on WWE's YouTube Channel.

19. Roddy Piper vs. Goldust: Art Imitates Life (Wrestlemania 12)

WWE / Via YouTube

In a moment infamously enveloped in the fog of homophobia, WWE booked Roddy Piper against "The Bizarre One" Goldust after the latter's hypersexual gimmick drove the late Razor Ramon away from their intended Wrestlemania collision. But with the new opponent came the opportunity to go further with the storyline, staging a "Hollywood Backlot Brawl" for the sole purpose of later imitating the O.J. Simpson Ford Bronco pursuit before ending the match in the arena with an incredibly offensive finale that saw Goldust stripped to women's lingerie before losing. 

Even disregarding the decision to parody a real-life murder investigation mere months after the trial's resolution, the disgusting display of intolerance in the name of entertainment remains one of the most objectionable and worst aged Wrestlemania moments.

Where to Watch: You can watch this clip on WWE's YouTube Channel.

20. Santino Marella Is Miss Wrestlemania (Wrestlemania 25)

Bob Levey / WireImage / Getty Images

In a moment that veers close to offensiveness but instead plows into embarrassing levels of stupidity and cringe, frequent comedy wrestler Santino Marella entered Wrestlemania 25 in disguise as his "sister," Santina, and was crowned as Miss Wrestlemania after winning a battle royale. In a moment aimed to bring bone-headed levity to the show, the moment would be less cringey if it didn't come at the cost of burying some of the most talented female performers on their roster, including Mickie James, Alicia Fox, the Bella Twins, Victoria, and Natalya. 

But professional wrestling, and WWE specifically, have long had to deal with a problematic past riddled with casual transphobia, anti-gay sentiments, and misogyny, so the booking and exhibition of "Santina" over their hard-working talent feels tasteless at best and straight-up punching down at worst. Oddly enough, this dense booking decision is still looked upon fondly by the company to this day, with "Santina" appearing once again at the 2019 Women's Royal Rumble Match.

Where to Watch: You can watch this clip on Peacock.

21. The Undertaker Commits a Murder?! (Wrestlemania 15)

WWE / Giphy

There are a lot of banned phrases in the WWE, most of which correlate with the personal vocabulary choices and desired branding from Vince McMahon himself. But chief among them are "murder" and "kill," with any performer talking about ending another wrestler's life often being met with scorn. But there's a difference between saying it and doing it, and WWE really went there at Wrestlemania 25, after a slog of a match between The Undertaker and The Big Boss Man was capped off with the former stringing up the latter with a noose in front and hanging him from the rising cell above them. 

Of course, the whole thing is gimmicked, and the late Ray Traylor wasn't actually harmed in the stunt, but for a company that trades in the marvel of choreographed violence, the depiction of a hanging on their biggest show of the year was truly baffling and unexpected.

Where to Watch: You can watch this clip on Peacock.

22. Roddy Piper Goes Too Far vs. Bad News Brown (Wrestlemania 6)

WWE / Giphy

In a match that has been essentially scrubbed from the internet following the WWE Network's sale to Peacock in 2021, Roddy Piper, known for his provocative and brash promotional stunts during his feud, challenged former Olympic medalist Allen James Coage, then known as Bad News Brown, to a match at Wrestlemania 6. While the feud was relatively tame for the most part, Piper went wildly off the rails on the day of the event, painting himself in half-blackface as to further instigate his interracial opponent. The move was received poorly back in 1990 and has only received more (rightful) criticism in the years that followed, but remained on the pay-per-view in its streaming versions until it was effectively erased from history last year, though those interested can comb the internet to find clips from the maligned match.

23. Trump vs. Vince (Wrestlemania 23)

UPI Photos / Scott R. Galvin / Courtesy Alamy

Vince McMahon and Donald Trump have been personal friends since the 1980s, with Trump appearing at multiple WWE events and even calling McMahon after the latter faked the demise of his onscreen character in a limousine explosion. But McMahon and Trump decided to pit themselves against one another in the "Battle of the Billionaires," an angle in which each figure would be in the corner of two wrestlers with the loser getting their head shaved. 

While the match itself between Bobby Lashley and Umaga was praised by critics, there's no denying that Trump was woefully unprepared for the world of in-ring combat, throwing the weakest punches in the company's history before delivering the worst sell of a Stone Cold Stunner ever. It's wrestlecrap at its purist, and the fact that we had an ex-president involved in a head-shaving angle at Wrestlemania proves that truth is indeed stranger than fiction.

Where to Watch: You can watch this clip on WWE's YouTube Channel.

There are so many things you can watch on Peacock for free, but if you want even more content, you can sign up for Peacock Premium for $4.99 a month or Peacock Premium Plus for $9.99 a month after a seven-day free trial.