Back in the late 90s, the landscape of pro wrestling was shifting. WCW was gaining power due to their “real-life” type of storylines, such as the nWo taking over the company with the use of “outsiders”. The WWE was suffering with outdated programming and they needed a big change.
That change would end up turning the Monday Night Wars on its head. The WWE switched focus and used a “Howard Stern” type of feel to their programming. All of a sudden, everyone was on the edge of their seats waiting to see the madness that would unfold. Eventually, WCW burned out and WWE held supreme in large part, because of their twisted, “Not So PG” content.
To McMahon’s credit, he pushed the envelope with himself at the forefront of most of the twisted acts. In this article, we include a variety of twisted moments that took place among himself and his family. For the most part, not only are these moments “Not So PG”, but they are also pretty darn creepy. From Vince and Stephanie locking lips backstage decades ago, to Stephanie and Shane recently kissing on-screen, we’ve truly have got it all in this article! Enjoy and like always, be sure to pass along the twistedness to a friend. Let’s begin, shall we?
15 Vince Appreciates Steph’s Goods
We start the article off with one of the many creepy Vince and Stephanie pictures. Who can forget those days of Vince uttering that creepy sentence, “you’ll always be daddy’s little girl”? Thankfully, in terms of creepiness on-screen, things have subsided big time with Vince taking time off from the television product, along with the new ratings system changing. However, we’ll always have the memories of such events to remember how twisted the McMahon family truly was, particularly Vince.
He pushed the envelope in this throwback moment. Stephanie was to renew her vows with Triple H in the main event, with her dad by her side. Before the wedding, Vince got a look at Steph’s dress and let’s just say his reaction was of the “Not So PG” nature, and one we’ll have no problems with keeping in the past. Although in fairness, the dress was truly a spectacle to behold.
14 Shane & Stephanie Share A Kiss
The relationship between Shane and Stephanie is much tamer in terms of creepiness compared to Steph and her dad. However, the two have both admitted that they’ve been very close, especially during their younger years when Shane was like a father to Steph, looking out for her while Vince worked countless hours running the WWE to its eventual global fame.
Eventually, Stephanie would gain power alongside her husband, while Shane ventured out into different interests. Many believe animosity existed between the two sides, although both have denied such claims. Shane’s long awaited return caused quite the stir from the WWE Universe as it rekindled his relationship with Stephanie. The two have been rivals thus far, however we did endure a creepy moment that saw Stephanie demand her sweaty brother plant a kiss on her after slapping him in the face... A weird and creepy trade-off it was.
13 Vince Makes Out With Trish... While Wife Linda Watches
WWE fans love to praise the Attitude Era but when you dig a little deeper, man, was there ever a lot more bad than there was good. Because of the ratings doing so well and bringing in record numbers, the good was that much more memorable than the bad.
The era pushed edgy content; the goal was to create a Howard Stern-type of feel to the program as that type of content was booming during the late 90s. McMahon himself took on the questionable and creepy skits, and this one in particular likely takes the cake. In terms of “Not So PG” creepiness, it’s hard to find something remotely better than this instance as Vince locks lips with the young and up-and-coming Trish Stratus. To make matters worse, the ordeal was done in front of a live audience, while his REAL-LIFE WIFE Linda, watched on completely paralyzed while in a wheel chair.
12 Dad Look At My Puppies
We continue with the creepiness showing yet another throwback shot from the early 2000s, featuring Stephanie and her dad Vince. Although this time, poor Triple H is also involved having to endure the skit live in front of his own eyes. Without a doubt, we believe all The Game was thinking was, “it’ll be yours one day, just go with it”. Looking back, he couldn’t have been more right as he’s now regarded as a close number two in terms of overall command in the company.
The creepy moment shows Stephanie giving her dad a quick flash. The Stephanie character was enduring a huge heel run at that point, although she would shockingly return later on with an entirely different persona, this time, as a babyface running SmackDown. She pushed the envelope even more sexually, although the twisted creepy skits with dad, were much more few and far between compared to the late 90s and early 2000s.
11 The Family Trash-Talking Mom
Poor Linda. As the lovable member of the family, Linda was on the wrong end of various skits and programs throughout her television time with the company. Looking back, she likely regrets taking part in a handful of these on-screen moments. Stephanie has admittedly regretted several incidents with her mother, and this is likely one of those as she trash-talks mom while she sits motionless and pretty much lifeless on a wheel chair.
With the agenda of gaining big time heel heat, the McMahon family made it a priority to pick on Linda. Stephanie was typically at the forefront of those attacks as she tried to gain more company power, while putting her mother in the rear-view mirror. The tactic worked, but man, was it ever tastelessly done. In an era like today's, we’ll never see anything of the sort again, and that’s definitely not a bad thing.
10 Vince and His “Not So PG Moments”
We give Vince credit for walking in the line of fire himself several times, but in some instances, it just got to be too much and just too creepy, to be quite frank. Looking back, McMahon has made out with a slew of former WWE Divas. Just off the top of our heads we can recall names like Dawn Marie, Torrie Wilson, Trish Stratus, Stacy Keibler and Christy Hemme, all making out with the boss on live TV. Being a married family man, the term to describe such moments is nothing but creepy.
He might have taken things even further in the picture you see above as he plants a kiss on Sable’s rear-end in front of a live audience. And yes, this was the same Sable that tried to sue him for millions just a couple of years prior to that moment. As if that wasn’t twisted and “Not So PG” enough, the two also shared a variety of steamy backstage moments.
9 More Brother/Sister Candid Love
This is a candid throwback shot featuring Stephanie and Shane sharing a moment together. Some would say they look more like husband and wife in this shot. The picture was taken just as the Attitude Era began to fizzle out. During that point, both Shane and Stephanie began to transition into different roles.
Stephanie would appear sporadically on WWE TV after the Attitude Era, usually appearing as an Authority Figure. She left a couple of times however with the interest of starting a family. Once she had three lovely daughters, Stephanie returned permanently both on and off-screen. As for Shane, things turned out quite different as he left the WWE taking his work-life overseas starting a Chinese On-Demand PPV type of service. The company wasn’t Shane’s best investment, and he’d eventually return back home to the WWE seven years after his departure. He’s been welcomed back with open arms since his recent return.
8 Shane Eats Steal From His Dad
Most of us have endured a good spanking as a kid, but eating a steel chair isn’t likely something most of us endured. This picture is regarded as creepy and “Not So PG” for different reasons. For one, chair shots to the head are now banned from the WWE due to concussion-type injuries. Back in the day, wrestlers like Shane would eat the chair straight to the skull with no form of blocking whatsoever. The photo is a poster child of what wouldn’t fly in today’s WWE. The irony of it all is that it features the boss flinging a chair at the skull of his own kid. Now that’s not PG, nor is it family-friendly, Vince!
Nowadays, you’ll still see chair shots, but they're usually tame in nature and never to the head. The example above is clearly “Not So PG” and hell, given the context, pretty darn creepy!
7 Vince Choking His Daughter... In An 'I Quit' Match
Looking back at brutal WWE matches, some can make the claim that the "I Quit" match is one of the very worst and barbaric. Just thinking about the Rock and Mick Foley match from the 'Rumble back in the 90s still sends shivers down our spines. Of course, Vince thought it would be a good idea to use a similar match featuring himself and, wait for it, his own daughter Stephanie!
In order to write Stephanie off the show, she was forced to take on her dad for control of the brand. The match was insanely uncomfortable to watch featuring Stephanie swinging a pipe at Vince, and Vince, choking his daughter to the point that she was blue in the face. The disturbing clash led to Vince picking up the win, while Stephanie was MIA for the next two years, getting married to Triple H in real-life just days after the bout. Putting things into perspective, she was getting choked by her dad one day and walking side-by-side with him down the aisle days after... You have to love the McMahons!
6 Hey Dad – Eat Pipe
We continue with the forgettable 'No Mercy' encounter featuring another creepy “Not So PG” shot of the bout. This one shows Stephanie swinging away at her father with one of the most dangerous weapons one can swing easily with, a damn led pipe! Looking at Stephanie’s role in the company nowadays, she likely hopes such a memory stays in the past!
Her in-ring involvement has been few and far between, despite that, she’s become one of the most hated heels of the last decade, which really says a lot about her character work. In terms of charisma and personality, few can top Stephanie, especially when it comes to generating any type of heat. We can expect the Billion Dollar Princess to step out of the office sooner than later, and return to television rekindling her rocky relationship with Kurt Angle. Oh it’s true. It’s damn true!
5 Stephanie Slaps Her Mom
As if verbally abusing Linda wasn’t enough, the company felt the need to take things a step further by adding a physical element to the attacks. Naturally, Stephanie was given the reins to take on these creepy, “Not So PG” acts. Whether it was slapping her backstage onto a couch, or in the middle of the ring, seeing such an act was rather disturbing and in truth, something very regrettable (even if it was during a free-for-all type of environment in the WWE).
When asked about regrets, Stephanie usually brings up two main instances; one was agreeing to make-out with Erich Bischoff, which was pretty disturbing, especially when you add in the fact that he was initially dressed as her dad. Second, Stephanie regrets the interactions with her mother, specifically slapping her. One can only imagine what was going through their minds during that skit!
4 Overprotective Shane
During the early portion of her WWE career, Stephanie was the polar opposite character to what we see today. She was a shy and quiet love interest of the late Test, as the WWE attempted to elevate his character in the role of a bigger player.
During that story, Shane played the role of the overprotective brother, feuding with the likes of Test over his sister. Who can forget Shane bringing his Posse alongside for the attacks? The entire ordeal was truly forgettable and one that WWE never really mentions. As a matter of fact, try thinking of the last time you recall the company showing any footage of Stephanie and Test together as a couple. Aside from on the worldwide web, memories of the relationship are few and far between when it comes to WWE television.
3 Father/Daughter Body Slam
In the early 2000s, SmackDown was truly must-see TV with the likes of Brock Lesnar, Hulk Hogan and The Rock bringing the show to new heights. Stephanie was in charge on-screen, and Paul Heyman was in charge outside of the ring with his brilliant creative mind elevating the show to its absolute peak.
The “Not So PG” creepy content continued however. This was another uncomfortable moment that we had to witness on route to Vince and Stephanie’s 'No Mercy' bout. While Stephanie and Sable got into a verbal joust in the middle of the ring, Vince felt the need to defend his mistress by taking things a step too far and body slamming (yes, body slamming) his own daughter. Nowadays, you won’t even see a wrestler lay a finger on a female, never mind body slamming them!
2 I’m The Father
Visually speaking, this might not look like the creepiest picture, but the hardcore wrestling fan knows the backstory to such a shot. While Stephanie was pregnant with her child, Vince came up with the disturbing, creepy, horrendous, “Not SO PG” idea to be deemed as the baby’s father, adding some heat to his feud against Triple H. Oh boy...
Stephanie admitted to this pitched story during Vince’s DVD, and she even claimed Vince was the one that came up with the concept. Stephanie admits she would usually agree to her father’s wacky ways but that idea was just way too much, and way too distasteful. Thankfully, such an idea was not given the green light although thanks to Stephanie, we know such a creepy concept was actually considered to begin with!
1 Father/Daughter Kiss?
This disturbing backstage moment took place during the McMahon-Helmsley era as the duo slowly began to take over. Heck, even Stephanie McMahon was a champion at that point recently winning the Women’s Title, a memory the WWE wants to keep in the past, that’s for darn sure.
In the creepy skit, Stephanie seems to be flirting with her father, asking him to give Triple H a match against The Rock. Everything about the skit felt so wrong. It ended with Vince telling his daughter he’d consider it and going in for a disturbing quick peck right on the lips. Seriously though, out of all the places to kiss your daughter! The moment took place during a wacky time in pro wrestling, so it became an afterthought quicker than it should have. In terms of creepy and “Not So PG”, this one takes the entire darn cake, folks!