10 Biggest WTF Moments In WWE Raw History

You don't make it to 25 years of age without making a scene or two...

Cultaholic is a celebration of all things professional wrestling, so we'll kick things off in an article that some might construe as a negative look on WWE by celebrating the fact that WWE Raw - the company's flagship weekly show - recently celebrated its 25th birthday. This is as big a WTF Moment you're likely to see when you really think about what an incredible milestone this is.

Raw has a quarter of a century of weekly broadcasts under its belt and is still going strong. Some might lambast the ratings achieved by today's shows, but with social media and all of the different ways you can watch the show in mind, the fact that somewhere between two and four million people still sit down to watch the show on the USA Network is some going.

Just like the times have changed, so has Monday Night Raw. You simply can't stand still when you're appealing to so many different demographics of fans, otherwise, you'll be left behind. Somehow, Vince McMahon and his team of creatives have managed to do that over a lifetime - and a couple of generations of those pesky millennials - even becoming the trend at least once during that time.

You just can't throw enough praise WWE's way for reaching this milestone. Just go and look at the statistics for your favourite show outside of WWE's umbrella of programming and compare the stats. Look at The Simpsons, for example. Homer, Marge et al might have started before Raw did but they've only amassed 629 episodes to Raw's 1286 and counting...

Right then, with those niceties out of the way, let's have a look at those moments that left our eyebrows located somewhere on our scalp and our mouths propping up the soles of our feet on the floor. Here are the 10 biggest WTF Moments in the 25-year history of WWE Raw...

10. Mae Young Gives Birth To A Hand


Love's young dream was running wild back in February 2000 as the hot couple in WWE at the time celebrated the arrival of their firstborn... hand. Honestly, if I could be a fly on the wall anywhere in the world it's got to be the room where ideas are thought up. The amount of LSD in that place could undoubtedly kill several herds of cows.

Mae Young was 77 at the time she went into labor, doing so just one month after she found out she was pregnant with 29-year-old Mark Henry's offspring.

On Raw, and after delivering the worst splash in the history of wrestling, swimming pools and baths, Mae collapsed in pain. She was rushed to the back and business was about to, and I'm sorry for putting this image in your head, fumigate a room, make Gerald Brisco throw up and Henry corpse uncontrollably.

It's a segment that included all of your dad's favourites. Farting, Young refusing to go through with the birth unless she got her hands on a cigar, period jokes and a one-liner that had all of us vomiting like it's New Year's Eve when Pat Patterson ended the segment by saying "let's give Mae a hand," BECAUSE SHE'D JUST GIVEN BIRTH TO A HAND HAHAHAHA LOL.

Let's allow your favourite uncle and mine, Dr Dave Metlzer of the Wrestling Observer, explain why Young gave birth to a Caucasian hand: "Luckily I do a radio show and someone explained that hands were popular sex toys in the 70s and 80s for women and I guess the idea was she was getting herself off in another decade and it had been there for a while."

That's Vince McMahon humour for you...

9. 'Pillman's Got A Gun!'


Imagine the uproar today if Braun Strowman threatened to fire a gun at Roman Reigns... ah the 90s was such a great time to be alive. I miss that decade dearly. However, even though this incident took place in a very different time where everything was about shock value on TV, this is a moment so controversial that it almost had Raw taken off the air.

Brian Pillman was a middleman of sorts in the Stone Cold Steve Austin/Bret Hart feud. With Hart only conducting promos from his home via satellite, the Texas Rattlesnake was feeling all kinds of insecurity and neglection. Hearing Brian use The Hitman's name in a promo sent Austin off the edge, and saw him break his former partner's ankle.

Tired of his two angle-mates cutting promos from their homes, Austin promised to go to Cincinnati and beat up Pillman in his own house. He tried to, with Brian waiting for him in his basement with his wife, Kevin Kelly, WWF's production staff and A GUN. Let's not forget we're still talking about the world of people dressing up in their underwear and simulating combat here... Doink The Clown, Duke "The Dumpster" Droese, A GUN.

How on earth did we end up here?

After beating up a couple of Pillman's friends outside the home - throwing one of them into a kid's paddling pool which was outside in the depths of November for some reason - Stone Cold had his foe losing his bananas inside the home, saying Austin 3:16 won’t be able to stand up to “Pillman 9 millimetre gun.” This was no toy gun, by the way, because Brian also said that he was going to send the Hollywood Bald "straight to hell," and I don't know how that's possible with something from Toys R Us.

To cut a baffling story short, Steve eventually breaks into the basement with the use of a tire iron, Brian aims the gun at him and we lose the satellite feed. Limbs everywhere. Everyone at home is losing their bananas now as we don't know if we've just seen the moments leading up to an attempted murder with a deadly weapon on a wrestling show. Thankfully, we didn't, because when the show came back on the air we saw Pillman's friends holding him back while Kelly tells us Austin disappeared due to the sight of the gun.

Austin is back once again, however, because in his world guns disintegrate into a pile of ash after 10 minutes. Brian's pals get in the way of a clear shot while the gun-wielding madman is now cursing live on air and shouting that he's going to kill Stone Cold before the show comes to an end. This is something that happened on WWE TV in 1996. It's madness. On two separate occasions, they build to an attempted murder with a deadly weapon with no payoff, thankfully. I didn't want to see Stone Cold die, he's my favourite.

The closest we get to death is Kevin Kelly choosing his words very carefully when he says nobody was "struck by the explosions," because when you fire a gun, a bomb comes out apparently. Props must go to Kevin here though, who by the time the show was going off the air for the second time, finally called for somebody to call the police - surely that's the first thing you'd do if you were a hostage intent on murdering the person trying to break into your own home...

A handgun on WWF Raw... There was a handgun on WWF Raw. Even for the standards of the day, it's absolutely bonkers.

8. Donald Vs. Rosie


'Left-leaning lesbian,' 'double-chinned Diva' - I want to die. Those are phrases Jim Ross called Rosie by the way, just so we're clear on that.

A man dressed up as Donald Trump (Ace Steel) fought a lady dressed up as Rosie O'Donnell (Kiley McLean) in a match that lasted seven minutes on an episode of Raw. There was cream cake eating, collar and elbow tie-ups and endless chants of "BORING" and "TNA" from a very disgruntled crowd.

The feud all stemmed from the real O'Donnell criticising Trump on The View for not stripping a controversial winner of Miss USA of her crown, apparently. Some tweets and other things happened - I'm not really interested in any of it as I'm sure you aren't either.

Anyway, Vince McMahon is good pals with The Donald, Donald doesn't like Rosie, so Vince made a mockery of Rosie on his show while having a playful little jab at his good pal's wig. BANTZ. 4. DAYZ.

Vince McMahon put his personal agenda to the fore even though he knew it would make his fans suffer to the point a chant for a rival promotion dominated the arena Raw was in. Silly Vince.

7. "Aw, Son Of A Bitch!"


Back in the day, The Undertaker and Paul Bearer came together to create The Ministry before going on a four-month spree of collecting rapscallions from all over WWF's roster. They eventually got to the stage where they had an army powerful enough to take on Vince McMahon's Corporation, good for them.

Eventually, Taker revealed that he had been serving a power far greater and more evil than he could ever be, definitely hinting at Satan himself without actually saying Satin's name in the same way that Brother Love would hint at religion without ever directly calling it out as such. He then claimed that he would take over the entire WWF in the name of this Greater Power, before going on a very personal tirade against the McMahon family that would see him abduct Stephanie - more on that later - among other things. Shane, the only McMahon The Deadman liked up until about 2016, had his Corporation join forces with The Ministry to form the Corporate Ministry - SICK remixed theme song, and all.

It looked like Shane O'Mac was the Greater Power as he took over control of the running of Raw from his father, but talk of this higher being refused to go away, hinting it could be somebody else. Then...



Jim Ross' disappointment spoke volumes for us all.

Rumours of Jake 'The Snake' Roberts, The Jackyl, Ted Dibiase and even Christopher Daniels were all rumoured to be in for the role, but Vince McMahon was the utter prick who was under the hood.

This meant The Undertaker had seized control of WWF in a tirade against Vince McMahon before handing it over to Shane who then handed it back to Vince again... and we'll end this point here because I'm getting dizzy.

6. The Apparent Demise Of Vince McMahon


**deep breath**

Vince McMahon kayfabe died live on Raw after Chris, Nancy and Daniel Benoit actually died - but before WWE knew about it - as part of that double murder-suicide and then all of a sudden Vince McMahon was alive and well again and the angle was cancelled.

**and relax**

WWE have officially listed this segment as 'Mr. McMahon's stages his own demise in a limousine explosion' on their YouTube channel and why not, I guess? Andy Kaufman did it (wink) so why shouldn't Vince McMahon? The plan, allegedly, was for Vince to return in the summer and for his accomplice in the whole charade to receive a massive push... anything to get to the top, right?

Vince lost the ECW Championship and had spiralled into a weird depression - I only say weird because he made funny noises and pulled funnier faces, not because I'm an inconsiderate arsehole. Eventually, a 'Mr McMahon Appreciation Night' was held in order to cheer the boss up. Names from the past - including Bret Hart who made his first appearance on Raw in 10 years from his home in Hawaii - showed up for the occasion before Vince came out to say "thank you."

Vince was then shown walking through the back past the entire locker room. They all looked sad, except for Paul London who was fired for grinning at the boss among other things even though he claimed nobody told him what to do. Looking around might have been an idea, Paul. McMahon then passed two lads smoking, looked back at them sheepishly, got into his limo before the thing exploded.

The show went off the air with Vince's car in flames and the body of the chairman presumably crispier than his bedsheets after a night of being one of those genetic jackhammers.

Oh, how we laughed...

WWE didn't though, releasing a very real statement via their website as well as flying the company's flag half mast at Titan Towers. What's worse is the fact Vince had several members of his roster cut promos about his life like they would if one of their comrades actually had passed away - this didn't sit well with fans and I'm sure performers alike who went through a similar experience with Eddie Guerrero less than two years earlier.

But hey, after these plans were scrapped at least we got the illegitimate son angle. That payoff softened the blow of this madness... like being faced with a Colonoscopy, but one where they use a MASSIVE LEAD PIPE instead of a small tube.

5. Shane McMahon Purchases WCW From Under Vince's Nose


**deep breath**

The name on the contract said McMahon but it read 'Shane McMahon' then we had to sit through The Invasion angle as WWF took on WCW's B-Team and ECW and then we were filled with disappointment.

The end.

**and relax**

Rumours of Vince McMahon purchasing WCW had been circulating for a while, and don't get me wrong, when it was confirmed he had done so it was massive. So big. Oh my god. This led us to the first massive WTF Moment in all of this which was seeing Vince McMahon's smug face on WCW programming - we'd see that same smug face around 50 times more than we had to during the course of the evening but I guess if I'd just toppled my biggest competition I'd be in the mood for gloating too.

Sorry, Jeff Jarrett...

Just picture that - following the biggest boom period in wrestling history, the leader of one company was broadcasting on the other's flagship show. Mental.

If that wasn't enough, Shane turning up and announcing that he had bought WCW from under his dad's nose was as big as it could have been, given the circumstances. The start to The Invasion was as good as it could have been before it all fell apart due to reasons beyond WWE's control.

We were all so excited, and all so let down by those guaranteed contracts getting in the way of our graps. Shame.

4. Ultimate Warrior's Eerie Promo


Self-Destruction of the Ultimate Warrior and the rest of it, after everything that had gone on between WWE and Ultimate Warrior during the previous 20 years, just seeing him back in the fold and in the Hall of Fame might just be enough to see him onto this list alone. Then we have the promo:

“No WWE talent becomes a legend on their own. Every man’s heart one day beats its final beat. His lungs breathe a final breath. And if what that man did in his life makes the blood pulse through the body of others and makes them bleed deeper and something larger than life then his essence, his spirit, will be immortalized. By the storytellers, by the loyalty, by the memory of those who honour him and make the running the man did live forever. You, you, you, you, you, you are the legend makers of Ultimate Warrior. In the back, I see many potential legends. Some of them with Warrior spirits. And you will do the same for them. You will decide if they lived with the passion and intensity. So much so that you will tell your stories and you will make them legends, as well. Ultimate. You are the Ultimate Warrior fans. And the spirit of the Ultimate Warrior will run forever!”

It's almost as if he knew...

3. The Undertaker Abducts Stephanie McMahon With The Intent To Marry Her Against Her Will And Perform A Ritualistic Sacrifice On Her


Remember that Higher Power debacle from earlier on in this article? Well at the time, we all thought this moment was the peak of The Undertaker being his dastardly worst in his quest to take WWF from Vince McMahon. All Vince had to do was hand over his company and his daughter would be fine but OOHHHH NOOOO, as The New Day would say. It turns out Vince doesn't mind the sight of his daughter in peril, seemingly on the way to being married to a demon against her will before being ritualistically sacrificed.

Doesn't a father always want the best for his daughter? Vince is weird, and this storyline wasn't really thought out too well when you look back at it.

The likes of Ken Shamrock and The Big Show tried to save the tied up Stephanie as Paul Bearer got on with the ceremonies in this 'unholy wedding' but were both seen off by The Ministry.

After Taker said "I do" in a way that would see any entry hole into your body seize up, Stone Cold Steve Austin - Vince's most bitter rival - came out to make the save because it was the right thing to do.

Let's just read the title of this entry again and see if our brains can compute what it's telling us: The Undertaker Abducts Stephanie McMahon With The Intent To Marry Her Against Her Will And Perform A Ritualistic Sacrifice On Her.


2. "From One Son Of A Bitch To Another"


When people tell you they'll only do something when hell freezes over, tell them it already has. It did so on July 15 2002.

Never mind the fact WWE kinda ruined their own shock appearance by having Eric Bischoff show up at the tail end of a Booker T interview just before Vince McMahon took to the stage the unveil the new Raw GM, the fact that Eric was there at all is an absolutely mind-boggling moment.

Eric Bischoff is the man who famously claimed that he would put Vince out of business, he's the man that tried to do so by fronting McMahon's stiffest competition of all time - he's a man who you'd believe wasn't on Vinnie's Christmas card list, never mind on the list to work for him. Vince is a very petty man, remember?

Eazy E arrived at the arena 15 minutes before the promo with Booker, waiting in a limo outside the arena until then. Imagine working for WWE and seeing that man walk in. You'd question what substances were in your water!

It's like seeing Kim Jong-un round Donald Trump's for tea. Completely unnatural. Ok, maybe not that severe, but you get my point.

1. Triple H Simulates Sex With A (Fake) Corpse


Triple H, dressed as Kane, talks filthy naughty to a mannequin pretending to be a corpse, gropes its breasts, removes its bra, removes its undercrackers, sniffs its undercrackers, claims there's "nothing like the smell of formaldehyde in the morning," gets himself naked, and then has sex with it.

If I'm honest, that's all I really want to say about this moment because it's absolutely dreadful. Watching it back just now was as hard as Trips was... NO! None of that now!

It's a moment that needs to be buried, burned and banished somewhere. It's also a moment that I don't really understand. I can see that Triple H is insinuating Kane is a necrophiliac, but he's the one in there dressed as the man he's slandering and actually doing it... the jokes on him, really... WWE is weird. Enjoy Raw 25!

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Ross Tweddell

Written by Ross Tweddell

Presenter over on the Cultaholic Wrestling YouTube channel. Email: [email protected]