We didn’t know it back in 1999, but Triple H marrying Stephanie McMahon would legitimately end up being the defining angle of modern-day professional wrestling. At the time, we thought it was a fun, silly little segment. We also somehow immediately pushed aside that Triple H essentially made it sound as if he drugged a woman and raped her. But it was simpler times back then.
Before the segment, WWE had just lost Vince Russo, the head writer and mastermind of the Attitude Era, to WCW. Stone Cold Steve Austin was in and out of the ring with various injuries. And WWE was attempting to take a career mid-carder who was never anything special in the ring, and propel him to the top in an effort to have a worthy heel to face their goldenboy, The Rock.
After the segment, WWE had a new major star overnight, and the road was paved for a new CEO in the future that would develop an entire brand to extend the quality of the company.
Also, he upgraded from Chyna to Stephanie fucking McMahon, which is probably the highest upgrade in the history of all things that are eligible for upgrades.
So what was this segment? Why did it work so well?
Is it “My Time” or not?
Wrestling is all about hype. You can call yourself whatever you want, but eventually the people will be the judge. Every single week, Michael Cole screams at the top of his effeminate lungs that Kofi Kingston is a legitimate WWE Champion. But it’s not true.
We all know it isn’t true. The dude was around for 11 years and was mid-card for a reason. He doesn’t have the look of a champion. He doesn’t have the promo capability. And he isn’t good enough in the ring.
Fans cheer, of course. We like Kofi. Seems like a great dude. We like New Day (though they are getting very stale very fast). But this is all filler.
Bobby Roode came in and called himself “Glorious”. Even was armed with a wonderful robe and an elite theme song. Certainly worked in NXT.
On the main roster he was looked at as a “Ravishing” Rick Rude dollar store knock-off, and eventually got treated as one. It’s very rare in WWE that somebody doesn’t end up where they should.
Even a guy like Dolph Ziggler is pretty much were he should be. He’s not quite Shawn Michaels. He’s not exactly Mr. Perfect. He’s not even really Billy Gunn. He’s just Dolph Ziggler. Never quite as handsome as we thought, didn’t ever show the promo chops we expected, and in the ring aside from selling, he’s basically just a decent guy.
Dolph gets dusted off every year for some type of upper mid-card angle, but that’s all. No need to get crazy.
In 1999, Triple H had his glorious “My Time” era. Armed with a great theme song, a brand new roided up look, and new entrance gear – this was the main event push he always wanted as he hid behind Shawn Michaels’ ass-less chaps for years.
But is this the new top heel? Or is it just Hunter Hearst Helmsley with some turtle wax to polish him up?
After attempting yet another “McMahon-the-boss-hates-the-talent” angle, except it was babyface Vince vs heel talent this time (yes this shit was even overdone 20 years ago), finally Triple H got his major showcase.
It was the wedding of Stephanie McMahon and Test. Test was another young guy in WWE who seemingly had a bright future. Tall dude with a decent wrestling style who couldnt talk.
The angle would conceivably get him over as well. But it didn’t, for reasons I’ll explain momentarily.
Let’s re-live the wedding of Stephanie McMahon and Test.
“Cowboy” Bob Re-Watches The Main Event Segment on Monday Night Raw on 11/29/99
- Weddings are generally fucking boring. So to end a live TV show with one had better promise to deliver.
- Wow, as I scroll through the chapters on WWE Network, Triple H faced Test on this show, before the wedding??
- And Test fucking WON??? Holy shit.
- I guess the thinking is that if the main event angle pays off, Test gets a rub too.
- Okay, it was with a chair and a special refereee with a fast count. But still.
- Oh boy, “last night in Vegas”, where Stetphanie has, for some reason, conveniently allowed WWE cameras and Fabulous Moolah and Mae Young to her bachelorette party, there are SEVERAL BOTTLES OF ALCOHOL. We are establishing that THERE IS MUCH DRINKING HAPPENING. And Stephanie takes a shot to SHOW SHE IS CERTAINLY DRINKING.
- Look, nobody ever credited WWE for subtlety, people.
- Stephanie is unbelievably hot in her 20’s.
- Stephanie is also unbelievably hot in her 40’s.
- Oh man. Okay, I have to fast-forward to the main event. But here’s a recap of the “Gravy Bowl Mach” between Jacqueline and Miss Kitty. It ended with the EMT, who shockingly happens to be an incredibly hot blonde with absurdly gigantic breasts, getting her top ripped off and thrown in the gravy. Her name is Barbara Bush.
- Man I can’t imagine how hilarious Vince thought that name was.
- God 1999 Michael Cole looks like such a pussy.
- 2019 Michael Cole also looks like a pussy.
- Cole is interviewing “Barbara Bush” who is acting like it was humiliating for her perfectly sculpted gymrat body to be exposed on national TV. I’m sure.
- Eventually, in a horribly acted segment, Barbara’s top is ripped off again.
- Whatever. This was better than the finish to Wrestlemania 35, so don’t feel all high-and-mighty, woke internet.
- Okay, back to work, “Cowboy” Bob.
- So here’s what is crazy about this fucking segment.
- They start off with Linda and the “bridesmaids” in the back. And Test “so nervous” backstage. This isn’t some “Oh, here we are back from the commercial break and shit is going down” wedding. They are fucking GOING FOR THIS. They are doing the walk down the aisle. The bridal party. The groomsmen. Wow.
- An ominous pan to Triple H, wearing a hilarious white rose on his black leather jacket, with Degeneration X, as Jim Ross screams “What are they up to?!” I feel like this is a huge mistake. Ruining the surprise. But probably done because, again, weddings are fucking boring and they don’t want us tuning out.
- What’s crazy is too, the “bridesmaids and groomsmen” are like mixes of real fucking people and wrestlers. Goddamn. It almost feels like the people Stephanie would have at her wedding.
- Who the fuck invited Shawn Stasiak?
- Test is friends with a ton of jobbers. (at the time! The Hardys and Edge/Christian weren’t “Gods of The Tag Division” yet.
- Mae Young might actually have been senile during this time.
- Test comes out to his own theme music for his wedding as the groom. If I get married, I hope my future wife is prepared for me coming out to Randy Orton’s theme. And doing the pose at the altar, of course.
- So again, this is being played totally straight. Like the priest in the ring is saying all standard wedding shit.
- Stephanie is such a horrible actress, as this is one of her first few months as a major TV character. She would rise to become the best heel in the entire company not long after this in a stunning turnaround.
- Linda McMahon never had a stunning turnaround in relation to acting.
- Holy fuck they even have wedding singers. This is glorious.
- Test is sweating bullets out there. Must be torture standing under those lights.
- The priest committing to the standard wedding shit.
- And then it happens, motherfuckers.
- “Should there be anyone who has cause why this couple should not be united in marriage, they must speak now or forever hold their peace.”
- You can feel the energy in the arena building. Wrestling fans aren’t that dumb. Prime opportunity for SHENANIGANS.
- In a stroke of genius, nothing happens. That’s surprising.
- Then. “Andrew, do you take—“
- That little extra moment to milk it and make you think “Huh. Nobody interrupted after all” makes all the difference.
- It’s Triple H with that white rose on his jacket.
- “Asshole” chants greet Triple H. Great sign.
- Vince’s fucking ridiculous angry face is wonderful as Triple H cuts to the video feed.
- Now normally, showing any video on a Jumbotron is fucking death for the live crowd, so this better be good.
- It’s Triple H, in Vegas, in a convertible, pulling up to a drive-by wedding chapel.
- HHH also points out that a sleazy motel is right across the street.
- Maybe the most unrealistic part of the entire angle is the 50 year old wedding chapel worker saying “Hey, you’re Triple H!” I’m sure that the fucking chapel lady is a devout WWE Monday Night Raw viewer and wondering how they are going to push their brand new heel.
- And the big reveal, a passed out Stephanie in the front seat.
- Hunter says “I do.”
- Then, in the most hilarious fucking suspension of disbelief, Stephanie, clearly passed out, is asked if she will take Hunter as her lawfully wedded husband. Triple H turns his head and says “I do!” in a fake female voice so awful that he isn’t even trying.
- And the retarded chapel lady buys it.
- Then they do vows. Which is overkill. The segment is now dragging. It’s so weird. Almost as if WWE for some reason is going through all the real stuff you’d have to do at that chapel. Why didn’t they just script this?
- Why would they say I do before the vows?
- So now they are legally married, in the type of over-the-top, absurd fucking segment that makes us both love this product and cringe when somebody else walks in the room.
- Oh, apparently the bartender was on Triple H’s payroll and drugged Stephanie. Good thing he’s on camera admitting this.
- “Go get the cans in the trunk. And not Stephanie’s.” Hilarious.
- “Get a nice shot of the brand new Mr. & Mrs. Hunter Hearst Helmsley.” And with that, they drive off. And history has been made.
- Cut to a crying Stephanie McMahon apologizing to Test.
- Now, here is where the push of Test instantly dies an agonizing death.
- While it is revealed later that this did not happen – this man just revealed that he DRUGGED YOUR FIANCE. He KIDNAPPED HER. He then FORCIBLY MARRIED HER. This is on video. And you stand there shaking your head in an “aw shucks gee whiz” way?
- This should’ve been Test screaming bloody murder and charging down the aisle, only to be held down by 15 fake security guards so that Triple H can come out and give his magnum opus closing speech.
- Triple H: “Now Vince, as a member of the immediate family, I know that you can only have one question on your mind…DAD…”
- Conversely, Stephanie’s God-awful “I hAtE yOuUuUu!” is her worst moment of all-time. Cringe at maximum levels.
- Seriously, no joke. I am an enormous Triple H mark. Then, now and forever. But his fucking emphasis on the word “DAD” here is one of his all-time best moments.
- Triple H, continued: “…not did we, but how many times, did we CONSUMATE THE MARRIAGE???”
- Okay, so now Triple H is flat-out asserting that he RAPED STEPHANIE after DRUGGING AND KIDNAPPING HER.
- “Triple H has married Stephanie McMahon!”, screams JR in all sincerity as Vince consoles his beloved daughter.
Goddammit, Vince. An angle so fucking stupid and ridiculous that it worked.
But that’s not all!
We can’t just have the main course without the delicious dessert, can we?
Triple H vs Vince McMahon, Armageddon 1999
Now we are at make or break time. Is this going to be a fun little segment that gets forgotten in the annals of wrestling history alongside The Shockmaster and the Gobbledygooker (or Katie Vick), or will it succeed in getting over your new top star?
With Test looking like a gigantic pussy by allowing the man who allegedly kidnapped, drugged and raped his fiance to get in some funny one-liners DURING HIS WEDDING, Vince McMahon did what he does often.
If you want something done right, you have to do it yourself. Nobody gives a fuck about Test. Time for good ol’ Vinnie Mac to make this work or die trying.
- Oh shit, this is the famous Miss Kitty bare boobs PPV. I won’t recap that part. The whole Barbara Bush thing was enough 1999 debauchery.
- I forgot the period where Miss Kitty was like Chyna’s lesbian submissive.
- Stephanie McMahon walks down to the ring to no music. She sits front row.
- So I wonder if they explain why Triple H is not under arrest for drugging and raping a woman after kidnapping her? In kayfabe I always assumed that you can hit people with chairs and shit because there’s some clause in a WWE contract that all is fair game during the show. But I think rape and kidnapping should be exempt.
- The first appearance of the now-iconic sledgehammer as Triple H makes his way down the aisle.
- Fun fact: “Cowboy” Bob used to work at a prominent investment bank. In his mid-20’s, when the manager was out of the office one day, he turned off all the lights, played Triple H’s “My Time” theme and walked into the office. He stood on top of his desk and spit out water like HHH.
- I got a huge pop too.
- The rare babyface Vince McMahon comes down to the ring, wearing a boring sweater. I think this is his gear for the WWE2k games. Not that I play those games at the age of 35.
- If anyone is listening, please get Yokozuna and IRS in those games STAT.
- Vince starts off by throwing powder in HHH’s eyes. Clever way to start out on offense.
- Vince is so God-fucking-awful in the ring, but the dude gets by on pure charisma.
- Also, he has a few matches north of 3 Bobs. His match vs Shane-O-Mac at Mania 17 is legendary.
- As horrible as Vince is (his clotheslines are even terrible), this match is so far structured exactly how it should be. These two are just running at each other, and Vince is trying to hurt Triple H as much as possible.
- Contrast this to bullshit that we’ve seen in WWE over the past few years. Remember when Paige told Charlotte that her baby brother, who died of a fucking drug overdose tragically at a young age, was rotting in Hell? And then Charlotte came out and they just had a wrestling match at the PPV? So stupid.
- This is way too much selling for your top heel to be doing for a 53 year old non-wrestler, but hey, suspension of disbelief and whatnot.
- What the fuck? It’s Foley with a shopping cart full of weapons.
- Vince looks GASSED as FUCK.
- Ah, smart little segment where Triple H tries to “wash the powder out of his eyes”, which is trying to get over that the only reason Vince had offense is because Triple H was “still blinded” from the powder earlier.
- “My dad is kicking your butt!” says Stephanie to a downed HHH. She would have better moments in the future.
- This match is terrible, by the way.
- Stephanie turning into the best mic worker in the entire company is pretty shocking. It would be like if in 15 years, Apollo Crews was blowing us away on promos.
- Vince rammed in the head with a shopping cart, which actually looked pretty brutal. You have to respect Vince going all out for his company, like he always does.
- This match is WAY TOO FUCKING LONG.
- “Cowboy” Bob comes from the future, and knows that the ending is good enough that the crowd would’ve went home happy. No need to lay around and watch Triple H beat up a 53 year old man for 40 minutes.
- As if this wasn’t awful enough for the crowd to sit through, now we are at a backstage portion. Again, always death.
- Triple H is somehow missing in the middle of a wrestling match. Now we’re outside looking for him.
- This is really bad.
- Fun “Cowboy” Bob fact: Mike Chioda has always been my favorite ref.
- Triple H tries to run over Vince with a car in a ridiculous sequence.
- I really wish I just recapped the end of this. But too much time has been invested and I must continue.
- You know what’s funny? Everyone always brings up how Triple H always has the longest matches at recent Wrestlemanias, and I always write it off as an old man who needs more time to tell a story. This is the dude in his prime in his early 30’s and the match is longer than the fucking Godfather.
- I bet that bodyslam on the limo, and even the subsequent Triple H elbow drop on the limo really fucking hurt both.
- I wonder if “I’m gonna drag this guy by the hair where I want him to go” has ever worked in real life.
- Somebody try it in a bar fight and let me know at email@example.com.
- Triple H climbs a high scaffolding. “Vince in pursuit of his son-in-law!” says JR without a hint of irony.
- Vince knocked off the scaffolding but it sounds like he fell into a soft pillow.
- Top quality blade job by Vince. BLOOD TELLS STORIES, WWE. Stop forgetting that. Then Triple H hits Vince with a fake gas can and it was either wonderfully gimmicked or he hit Vince really fucking hard.
- Triple H on the mic now. “Tell me how it feels, baby.” to Steph.
- Triple H with a fantastic little heel moment, telling Stephanie she’ll never have to ask where daddy is again, because her daddy is standing right here. Gets no pop though, because the match is so fucking bad.
- Triple H holds bloody Vince in front of Stephanie in another heel masterclass.
- The sledgehammer makes an appearance. Who knew how popular it would get?
- It was always so silly, of course. Still is, today. IT’S A FUCKING SLEDGEHAMMER. It should kill people.
- Vince about to beat HHH with the sledgehammer as the crowd finally wakes up.
- Steffo jumps in the ring though. Taking lessons from Charlie Chaplin, the silent film great, she wildly over-pantomimes “NO, LET ME TAKE THE SLEDGEHAMMER, BECAUSE I WANT TO HIT THIS MAN!”
- Surprisingly big pop for the prospect of Steffo hitting HHH with it.
- “Is this spousal abuse?!” cries JR in a pretty funny moment.
- Triple H gets up though, steals the hammer from Stephanie, and then beats the shit out of Vince with it. Stepping on him with one foot, a la Warrior over Savage, for the pin.
Give it 1 and a quarter Bobs for effort, but man was that meandering and painful to watch. Post match is what we’re here for.
- Triple H, the dastardly heel he is, holds up the sledgehammer and essentially threatens to murder Stephanie McMahon.
- She turns around and sees him.
- And then…
- That smile.
- Stephanie and Triple H hug in the middle of the ring to a MONSTER FUCKING POP.
- “For the love of God!!! What is this?!?!” — JR
- Both raise their hands is triumph and KISS IN THE RING as the crowd is stunned at the balls of these cheesy soap opera hijinks.
- Glorious. Charles Dickens wishes he ever wrote shit like this.
- Hand-in-hand, Triple H walks out with Stephanie McMahon, and the unquestioned top heels of the company are born.
So let’s recap:
After the events of Armageddon ’99, it turns out Stephanie McMahon decided she hated her dad, and didn’t want to marry Test. So she banged Triple H on the side, and the two of them faked that Stephanie was drugged, kidnapped and raped by Triple H.
Stephanie staged a fake wedding, to have Triple H invade this fake wedding and shock the world with the fake footage. Stephanie did all of this to manipulate her dad into a no-holds barred match to get the living fuck beaten out of him by Triple H.
She then waited for the perfect moment to pretend she wanted to attack HHH with a sledgehammer, only to purposely allow HHH to steal it from her and nearly kill her father.
She then had Triple H fake like he was going to hit her with it, and then turn around and hug him instead.
Why did they do all of this? Why go through with it? Why not just say fuck off Test and dad, I’m banging Triple H now?
The story pained me to put together right now, as it logically just falls apart at every opportunity.
But guess what? It was fun, it was ridiculous, it was absurd, and it was genuinely all very surprising.
And I think it’s safe to say this worked.
Triple H and Stephanie McMahon not only ruled over the WWE in kayfabe from 1999 to present day, but Triple H is now COO of WWE.
Triple H traded in Chyna, who literally looked like a man, for Stephanie. Stephanie is still gorgeous and they have a beautiful family to this day. Chyna made porn with X-Pac and is now dead.
Test looked like a cowardly buffoon and is now dead.
Vince McMahon still thrives and was taking headbutts from Kevin Owens as recently as a year ago.
And you know what the kicker is? Right after Vince Russo left for WCW and talks of storyline direction was hanging in the balance, WWE fucking out-Russos Russo for a cockamamie plan so ridiculous that it was behind the guy’s wildest dreams.
So why not do something this ridiculous again? Why not swing for the fences and go full-on embarrassing soap opera?
With Fox stating they want Smackdown to be more “athletic oriented”, I think schemes like these are firmly in the past. And it’s a shame, because you can argue this was the greatest angle of the past 20 years.
It may have taken a staged drugging, raping and kidnapping, plus a 40 minute fucking beating of a 53 year old billionaire, but in a span of a month, Triple H went from mid-card loser and Shawn Michaels’ Degeneration X butler to the top heel in all of professional wrestling.
Now that’s how you get a dude over.