15 Stephanie McMahon Pictures That Drove Triple H Crazy

For the most part, Vince Russo was an absolute tool, but he did come up with some great ideas that deserve some praise. One of them was encouraging the debut of a young Stephanie McMahon onto WWE programming. She began as the innocent love interest of Test, and would turn into one of the most villainous females in WWE history. We can all agree, the gamble on Stephanie has worked out quite well.

You figure being the boss’s daughter and the real-life love interest of a WWE Superstar would limit Stephanie’s edgy involvement but we can safely say it did not. Particularly in the late 90s and early 2000s, the company was all about pushing the envelope sexually and for some reason, Stephanie was involved in a plethora of those moments. From HLA action to making out with Rikishi, Steph’s antics weren’t exactly PG material.

In this article, we celebrate those very moments that likely infuriated Triple H. He loves to spit out his water during entrances but we have reason to believe that he spit it out for other reasons after witnessing some of these moments his wife had to partake in. Enjoy this list of 15 Stephanie McMahon pictures that drove Triple H crazy. Like always, be sure to engage in conversation via our Facebook page and share the link with a friend!

15 The Wardrobe Malfunction

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In the world of sports and entertainment some things can go wrong rather easily. Whether it be botching a maneuver or forgetting a scripted line during a promo, the likelihood of embarrassing yourself is much higher for a WWE Superstar. Another type of botch that’s normally beyond ones control is the good old fashion wardrobe malfunction. With performers dawning chizzled body types along with wearing tightly fitted attired, the likelihood of a malfunction going down is quite high.

Even the billion dollar princess was susceptible to such an incident, twice for that matter. The more well known altercation took place while she was between her husband’s crotch. Wearing a tight top, one of Steph’s puppies came out. The picture you see above is another malfunction as Stephanie’s undergarments seem to be showing as she enters the ring. Surely, Triple H pedigreed the photographer for getting such a shot.

14 The Candid Shot

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Of course, a major part of the WWE’s ongoing machine is the fans. Without the WWE Universe, there simply wouldn’t be a product. One of the best parts of being a fan is attending a live show, I can’t tell you how many times most of us left a WWE event thinking, “I want to become a wrestler”. The allure of it all is truly surely for a fan.

The most surreal part of the experience is seeing some of your favorite Superstars live. In this picture, a fan takes advantage of his awesome seats and snaps a glorious picture of Stephanie as you get a wonderful glimpse of her toned backside. Candid pictures of this nature are the norm nowadays, heck Sasha Banks as her very own Twitter account of candid booty pics.... Thankfully for Hunter, that hasn’t been made of Stephanie but we wouldn’t be surprised if it was at some point.

13 Stephanie In HLA Action

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The WWE was a weird place in the early 2000s. The likes of Eric Bischoff were back in the company while the promotion was still operating in an edgy manner. Heck, Vince even proposed an incest storyline alongside his daughter and if that wasn’t bad enough, he even pitched the disturbing idea of being the father of Steph’s child. Thankfully, the more cool headed McMahon put her foot down and rejected both stories.

What she didn’t get away with however was an awkward encounter as she took part in some HLA action. This is a PG site so if you don’t know what HLA means, Google it but we’re pretty sure this picture makes it rather clear. Steph took part in this cringe worthy angle and Hunter was likely slightly enjoying it at the time. Now a proud mother of three, the baby daddy Hunter is probably wishing he can go back in time and erase this footage.

12 Making Out With Rikishi

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So what’s worse than engaging in some HLA action you ask? Well, how’s about making out with a 500 hundred pound man (okay we exaggerate) that likes to wear thongs to the ring, while backing his bum up in the face of his opponents. Of course, we’re talking about WWE Hall of Famer Rikishi who most of us still haven’t forgiven for failing to mention his Too Cool brothers during his HOF speech. Shame on you Kishi, but that's a topic for another day.

Rikishi would come in to end the HLA angle dawning a wig and making out with Steph. As if that wasn’t bad enough, the two would start grinding up on one another as Steph rubbed her backside on Rikishi’s...lower midsection. It might have been the first time ever most human beings wanted to be Rikishi for that split second of grinding and making out.

11 Steph At Hugh Hefner's Mansion

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Don’t mark out just yet; no, Stephanie did not pose nude for Playboy, but she did however accompany the lovely former WWE Diva Torrie Wilson to the mansion when her beautiful blonde head of hair graced the cover of the magazine. Of course, Stephanie was covered from head to toe rocking a corporate pantsuit we can only assume came from JC Penny.

The picture isn’t the worst on the list, but given the WWE’s status as a publicly traded company, we best believe Hunter thinks this photo is not best for business. Stephanie is the current Chief Branding Officer of the company and she was very influential in changing the WWE’s product rating to PG in order to satisfy the many investors. WWE was a different company back in the day and we don’t expect such relationships with an edgy company like Playboy to continue at any point given their newfound professionalism as a publicly traded company.

10 Flirtatious GM

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We continue with the weird early 2000 era featuring a photo of Stephanie’s run as the SmackDown GM. Man have times changed since then looking at the clean cut Kurt Angle and Daniel Bryan leading their respective brands nowadays.

During Steph’s initial run on top with SmackDown, her role was drastically different. For the second time in her career, Steph was a babyface as a fan favorite. Along with that, she was flirtatious with the Superstars while rocking some edgy outfits that either were very short looking or featured some serious cleavage. Whatever the outfit was, we have reason to believe Triple H was sweating a little bit more. Ironic that Stephanie would eventually step down and be written off television to marry Paul and later, give birth to three daughters. Now were not suggesting Hunter got her off TV purposely during her edgy run, but the timing was quite ironic wouldn’t you say?

9 Partnering Up With Test

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Vince Russo made a mess of a lot of things, but suggesting Stephanie use her talents on screen was a brilliant move. After getting crucified by ‘Taker only to be saved by Austin, Stephanie would move on to other things which included being romantically linked to Test. The story was a complete work as it was meant to elevate the late WWE Superstar. The Canadian had some high profile bouts while with Stephanie including a Summerslam bout versus Shane with the stipulation of a “Love her or Leave her” match. Yes, the WWE was a weird place back in the 90s.

Ultimately, their love story would come to an end with Triple H intoxicating Stephanie and marrying her. That would later launch her villainous character that would take over the WWE alongside Hunter. Kind of surreal that the story seems to be playing itself out in real-life nowadays as the couple continues to gain power behind the scenes.

8 Orton's Kiss

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You figure being the boss’s daughter Stephanie would be immune to kissing others on-screen but it turns out it was the exact opposite. Steph locked lips with several WWE stars and one of the most disturbing had to be the incident that saw Randy Orton kiss her while she laid unconscious in the middle of the ring. To make matters worse, Triple H watched on handcuffed in the corner.

It was meant to add to their WrestleMania encounter but looking back, we believe all three of the parties involved would like to forget it ever took place, particularly given the WWE’s stance on men and women violence. Heck, we hardly ever see inter-gender tag matches anymore, that’s how sensitive the WWE is on the issue. Looking back, this picture likely drives both Triple H and Stephanie crazy.

7 Eric Forcing Himself On Stephanie

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We here on The Sportster aren’t sure who was more irate at this incident taking place, whether it was Triple H himself or Stephanie who was forced to partake in the weird kissing angle amongst GMs that went absolutely nowhere. Stephanie discussed two regrets on the Talk Is Jericho Podcast during her career and one of them, was kissing Eric. Ouch, poor Easy E just can’t catch a break when it comes to WWE things.

What made everything so much worse was the fact that there was no carry over, it was a one and done incident that closed off SmackDown. Maybe there was more to it, but Stephanie simply refused to go any further. Triple H was likely cringing at the sight of the incident, likely spitting out his water for real.

6 The Kurt & Steph Love Story

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Aside from his former partner Chyna, Hunter never really had any love interests during his WWE run (Sable being his valet doesn’t count, don’t try to be smart). Stephanie on the other hand did and it likely didn’t sit well with Hunter. One of the very first Stephanie love triangles took place when Kurt Angle entered the picture. Kurt was absolutely brilliant in the skits and that’s all thanks to his skill at memorizing dialogues. Angle admitted himself that he ever wrote any of his lines but he had an insane skill of remembering them word for word. His acting prowess led to some awesome segments, and it eventually led to Stephanie and Kurt locking lips, something Hunter probably wasn’t too pleased with.

Whatever the case might be, the love triangle was absolute gold... oh it’s true... IT’S DAMN TRUE! Music hits, "you suck" chants proceed.

5 Steph Loses Her Top

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In terms of cringe worthy moments for Stephanie, most of them took place during the Attitude Era. The WWE had the luxury of pushing edgier content and boy did they ever take advantage. Even the boss’s daughter went shirtless at one point in time during a skit with Steve Austin.

It seemed forbidden for Steph to go shirtless, which is why it added to the allure. The WWE wanted to play it off as a wardrobe malfunction, but obviously, the goal was to create another spectacular 3:16 moment. As Austin ripped off the vender’s bag from Stephanie, along with it came her shirt which was ripped off. The crowd popped like crazy as Stephanie rushed to the back topless in just her bra. We have reason to believe an irate Triple H was waiting at the gorilla position with a towel as soon as she went backstage opening the curtain....

4 Getting Spanked By Cena

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Looking at the state of the WWE nowadays, you can’t help but to laugh at the fact that such an angle took place. Stephanie is a huge advocate for women empowerment movements as she’s extremely high up in the company while John, is the ambassador for the WWE being a top role model to millions of children around the world. Kind of surreal to think that such faces took part in an angle this twisted.

It took place during Steph’s run as SmackDown’s GM. The company was extremely high on Cena and they gave him this angle to likely boost his name. He spanked Stephanie in the middle of the ring and we can only assume Triple H spanked her even harder at the end of the night... Not many can say they spanked their boss...but Cena can.

3 Test Gets Aggressive With Stephanie

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This picture isn't forbidden because of the adult nature but instead, it is because of the violent connotations between a male and female. Today, the WWE has no tolerance for such antics making this a picture both Triple H and the entire WWE don’t want us to see.

Nowadays, the landscape is completely altered since the WWE became a publicly traded company. If an encounter is to take place between a male and female, it likely shows Stephanie slapping a male Superstar while getting untouched. We feel bad for wrestlers that had to endure a Stephanie slap as according to Chris Jericho, it’s one of the worst experiences as McMahon doesn’t hold back when throwing the open-handed shot. We have reason to believe Hunter encourages Steph to use as much force as possible...

2 More Kurt Moments

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Both Stephanie and Kurt would continue their edgy ways during Steph’s run as the SmackDown GM. They took part in a steamy scene which was quite cringe worthy for Hunter, thankfully though, it was all a tease as nothing would come from it. Fans are quite eager to see these two, together again on Raw at some point.

As a mother of three daughters, those days for Stephanie are way in the past. Her on-screen character is met in a high regard and rarely is she ever putdown by any WWE Superstar. This is likely to continue as Stephanie has recently entered her 40s. Her days of being the brunt of a joke are over and it looks like her power off-screen will only continue to grow as time goes on.

1 The SummerSlam Kiss

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SummerSlam 2014 was a special moment for Stephanie as she returned to the ring picking up her first win in over ten years. When recalling her top moments in the company, Stephanie picks her story with Brie as one of her favorites of all-time. The company was very invested into the match as the two even closed off shows going face-to-face with one another.

As we stated, Stephanie would go on to win the match. It wasn’t a classic by any means but still, a pretty cool moment. Hunter would enter the ring congratulating his wife but the kiss made all the headlines for the wrong reasons. The photo circulated online as fans drooled over Stephanie’s outfit in the tight leather attire. Fans got a nice glimpse of her backside instead of enjoying a heartwarming kiss from her husband. Verdict, Triple H was not pleased...

Game Over.

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