15 Times The Billion Dollar Princess Embarrassed Vince McMahon

Vince McMahon's two biggest loves in this world have to be wrestling and his family. When those two things intersect, there can be problems to be had.

One of Vince McMahon's prized possessions and accomplishments is undoubtedly founding the company now known as World Wrestling Entertainment. Climbing up from the stenches of poverty, The Chairman scratched and clawed his way to get to where he is today and it has all led to him being the owner of a billion dollar company. The only thing that Vince McMahon probably cherishes more in this world is his children, Shane McMahon and the Billion Dollar Princess, Stephanie McMahon. Stephanie herself has proven to be a valuable behind the scenes asset to the company as both the Chief Brand Officer and on-screen heel authority figure in the same vein as her father once did. Opposed to being labeled as some entitled brat, Stephanie McMahon has managed to prove her worth with the company to the point that she deserves to be heir to the throne one day. However, as much as Vince McMahon loves his daughter, there is no doubt he might have embarrassed her on more than one occasion.

Vince McMahon's two biggest loves in this world have to be wrestling and his family. When those two things intersect, there can be problems to be had. Vince has been noted to be a critical backstage figure when it comes to getting his vision on-screen in the most perfect way possible. There is no question that he is probably just as critical towards his family when he decides to bring them into his vision in front of the camera. Stephanie McMahon has probably felt and heard the wrath of her dad whenever she flubbed up in front of the camera in some way or another. Let's not even mention the personal, real life controversies that the Billion Dollar Princess has been embroiled into over the years. On second thought, let's mention all of these controversies for the sake of this list. Here are 15 times Stephanie McMahon embarrassed her dad, Vince.

15 The Daniel Bryan Affair Segment

Sooner or later, when a wrestler works in the business long enough, they will take part in a bad wrestling segment. However, only a select few of competitors get to have an excruciatingly bad wrestling segment. To the chagrin of Vince McMahon, his own daughter is one of those select few. One of her worst segments came about on August 11th, 2014 when she brought out Daniel Bryan's "physical therapist" Megan (aka future Tough Enough competitor Chelsea Green and TNA employee Laura Van Ness) to accuse Bryan was cheating on his wife, Brie. Much of the segment was booed, received "NO!" chants, and perhaps due to Vince's own displeasure with the segment, the video of the segment posted on WWE's YouTube page has been heavily cut. The much lengthier 10 or so minutes that the segment actually ran was cut to about 3 minutes. Also, the segment received such bad reviews that the angle had been retconned, forgotten, and not even mentioned the following week.

14 Her Wardrobe Malfunction

It probably doesn't need to be stated or emphasized that Stephanie McMahon is a rather voluptuous woman. That fact is as clear as the day is long and that fact was never more clear than during her wardrobe malfunctions. She's actually had a couple wardrobe malfunctions on camera, but the most glaring happened on a 2002 episode of Raw when Triple H attempted to Pedigree his future wife through the announcer's table. In the heat of the moment, Stephanie's breast popped out for all the world to see. Stephanie has said herself in an interview that it's her most embarrassing on screen moment and it's probably safe to say that her father was just as embarrassed to have captured the snippet.

13 The HLA Segments

Back when Eric Bischoff was still working for WWE as the Raw General Manager, one of his cash-making schemes to help Raw's ratings skyrocket was his HLA segments. HLA, which stands for Hot Lesbian Action, would feature, you guessed it, hot lesbian action. He'd just bring in a couple of random, stereotypically sexy women and they'd spend a couple minutes fellating each other onscreen for a much needed ratings boost. After losing a wager with Bischoff, SmackDown GM Stephanie McMahon was forced to take part in an HLA segment at Unforgiven 2002, which included two anonymous lesbian rubbing and kissing all over Stephanie. Vince has made it no secret that he loves viewing his fair share of hot lesbian action on occasion, but seeing his daughter take part in such a segment probably gave him second hand embarrassment while watching it backstage with a room full of fellow producers.

12 Name Dropping CM Punk

One of the most embarrassing fallouts that both Vince McMahon and the WWE have suffered was CM Punk's public 2014 walkout of the company. Things didn't help matters when he went on Colt Cabana's podcast and aired out all of WWE's dirty laundry regarding their doctors, their final meeting, and him getting fired by the company on his wedding day. The current lawsuit that both parties are in the midst of have convinced Vince to try and keep Punk's WWE existence quiet and in the past. His daughter, on the other hand, has name dropped CM Punk the last couple times Monday Night Raw hailed from Punk's hometown of Chicago. In both instances, Stephanie essentially called Punk a loser in front of the crowd, even going as far as to mention his shattering UFC loss. Considering The Rock reportedly got chewed out backstage for calling CM Punk in front of the live crowd during his last visit, Vince probably wasn't a fan of Stephanie mentioning Punk either.

11 When She First Started Dating Triple H

For a man who likes to keep such a professional conduct in his business, Vince McMahon likely wasn't the most comfortable when it comes to the idea of his daughter dating one of the boys in the locker room. In fact, it's one of those unspoken rules of the business. That goes for every business on that matter, but things can get especially messy when someone mixes business with pleasure within the wrestling industry. Which is why Vince probably didn't take it too kindly when he caught wind of Stephanie McMahon fooling around with The Cerebral Assassin, Triple H. As we all know by now, Vince is more than happy with their union now and in more recent years has been one of the couple's most avid supporters, but he probably wasn't so supportive in the beginning of their relationship. Both Triple H and Stephanie have spoken in a handful of interviews in the past about how awkward things were at the dinner table at first. He probably hated it when their relationship went public knowing the backlash that Trips could get from it, being accused of family favoritism regarding his pushes.

10 The Incest Angle

We all feel a little embarrassed when we have to ask anyone a question, fearing to be denied or shut down in some way. Especially when the question is along the lines of "Can I be the on-screen father to your love child?" When Stephanie McMahon found herself pregnant in 2006 with Triple H's baby, her father asked if he could make a storyline out of the situation. Not just any storyline, but an incest storyline. That's right, Vince wanted to be his daughter's baby daddy on TV. Naturally, Steph was creeped out and turned the angle down. So, thinking he was making matters better, he suggested her brother, Shane, could be the father instead. Again, Stephanie turned it down. Vince probably feels silly for asking to begin with and apart from when they went over it for his McMahon documentary, he probably wants to forget he even asked and never talk about it again.

9 Her Match With Jacqueline

On January 17th, 2017, WWE promoted the Steel Cage match between Becky Lynch and  Alexa Bliss for the SmackDown Women's Championship as SmackDown's very first main event for the Women's Championship. Though it may seem like a fitting first ever SmackDown main event for the women's division, the fact that it's the first of its kind in SmackDown history isn't exactly true. Although, when you see the actual first SmackDown main event for the Women's Title, you'll understand why both Vince and Stephanie McMahon want it buried in the past. The actual first ever SmackDown main event for the Women's Championship on March 30th, 2000 between Stephanie and champion Jacqueline. However, the match barely went two minutes and was more of an angle where Steph won thanks to interference from DX. Not exactly a moment fit for the Women's Revolution that WWE is promoting.

8 Her Match With Vince

For a man who is the farthest one can get from being an actual legitimate wrestler, Vince McMahon has had a handful of great wrestling matches. Matches between Vince and the likes of Shawn Michaels, Hulk Hogan, and Stone Cold Steve Austin have all been highly praised in the past. He even had a show stealing contest with his son, Shane, at WrestleMania 17. Unfortunately, he couldn't produce the same magic with his daughter, Stephanie, when the two tangled at No Mercy 2003 in an I Quit Match. Perhaps the whole atmosphere was uncomfortable more than anything else to see a grown man brutalize his own daughter in front of a live audience, but the match has been critically and seemingly universally panned. Not only as one of the worst matches of either competitor's career, but one of the worst matches in WWE history. Given how much Vince prides himself on producing great wrestling matches as both a wrestling producer and wrestler, he might be a little embarrassed he had such a bad match with his daughter.

7 Her Howard Stern Interview

Anyone who is remotely familiar with Howard Stern knows that conversations on his show tend to get a little kinky most of the time. Nothing is or has ever been off limits for discussions towards guests on The Howard Stern Show. Topics and questions always veer towards sex on that show and in the most explicit manner. Stern certainly did not make any exceptions or change the format when he had Stephanie McMahon on as a guest in 2002. In all likelihood, this might have been an interview that Vince chose to skip out on. If he did decide to tune into this one, he would have heard his daughter talking about how she likes her sex with then-boyfriend Triple H, how she likes it hard, when she likes it soft, etc. Had he heard anything about the interview, he had to have been red in the face after hearing what was coming out of his little girl's mouth.

6 The Booty Slap Heard Around The World

For the past 12 years, John Cena has successfully molded himself as a role model fit for being the face of WWE, but in 2002, things were a very different story. Fresh off of developing his rapper character for the first time and slowly moving his way up the card on the SmackDown roster, he found himself in a segment with Stephanie McMahon. Stephanie, who at the time as SmackDown General Manager often used her "assets" to titillate the crowd, politely asked Cena to slap her booty. And Cena did not hesitate to oblige her. In front of the thousands in attendance and the millions watching at home, Cena gave his boss' daughter a big ol' smack on the rear end. Speaking of the boss, given how this segment doesn't fit the PG nature of current WWE programming or Cena's current character, he probably gets second hand embarrassment knowing there's footage of his poster boy getting up, close, and personal with his daughter. Had he known how valuable the Leader of the CENAtion would become in the future, Vince probably would've never booked this segment.

5 Her "Accident" At Payback 2014

No one likes being known as the parent of a kid who pissed their pants in public. Especially if that kid is an adult woman and heir to a billion dollar company. But that was exactly the case at the Payback 2014 pay-per-view. In a segment that night where Brie Bella slapped the taste out of Stephanie McMahon's mouth, Stephanie's mouth dropped in astonishment and she looked genuinely shook up. Either that is a display of tremendous acting on Stephanie's behalf, or Brie Bella smacked her so hard that she literally slapped the piss out of her. Turns out it was the latter given how shortly after the slap, Stephanie stormed out of the ring and the camera caught a brief glimpse of a seemingly wet residue streaming down her backside. Social media quickly brought attention to the blink-and-you-miss-it moment and quickly afterwards, the clip was pulled from the WWE Network. No word on whether Vince McMahon or Stephanie called for it to be removed, but surely both parties would like to forget that moment ever happened.

4 The HHH/Chyna Scandal

Vince McMahon tries at all costs to keep controversy away from his company, but that becomes extremely hard to do when his own daughter is in the midst of it. As we all know, Triple H and Stephanie McMahon were merely co-workers when they started working as an onscreen couple. Then, life began imitating art as the two pursued an actual relationship and now, they are WWE's resident married power couple. On the surface it's kind of a romantic story. That is until we recall that Triple H had been seeing Chyna for years at this point until Trips started cheating on her with Stephanie. Numerous interviews from numerous perspectives (including Chyna's) have recounted Chyna being heartbroken over her falling out with Triple H. While there were other factors that led to Chyna's eventual release (money, her demands, etc), this affair didn't help matters on her way out the door. Vince probably isn't keen on the fact that even to this day, the fact that his daughter was essentially a homewrecker years ago still gets brought up.

3 Her 9/11 Comment

In the wake of the September 11th attacks, we all found it difficult to make sense out of such a senseless tragedy. We all had to find a way to cope and rationalize what went down that day, but perhaps Stephanie McMahon could have chosen her words more carefully when rationalizing the attacks on a national platform like WWE TV. On the first SmackDown after 9/11, several segments were aired throughout the night showcasing superstars giving their reactions on the event. One of the those superstars happened to be Stephanie McMahon, who made the ill decision to compare the terrorist attacks against America to when the feds indicted her father during the infamous steroid trial of 1993. It's one thing for Stephanie to bring up old demons from Vince's past. It's another for her to make such an appalling comparison and bring a media hellstorm to her father's doorstep. Both herself and her father probably would like to keep this moment stuffed deep in the WWE vault.

2 The Titus O'Neil Incident

Anyone who remembers this incident last year may forget that Stephanie McMahon herself was the catalyst for Titus O'Neil nearly getting fired. As Raw was going off the air following Daniel Bryan's retirement speech, cameras caught a glimpse of Titus pulling in Vince McMahon by his strong arm. Titus claims that it was all because he wanted Vince to be a gentleman and let his daughter walk ahead of him instead of vice versa. Vince responded to Titus' public display of horseplay by suspending him for 60 days. If not for backstage cohorts telling Vince he was being irrational, Titus would have initially been suspended for 90 days and potentially fired. If Stephanie wasn't in the wrong place at the wrong time, perhaps Titus wouldn't have done what he did to make Vince feel humiliated, emasculated, and embarrassed enough to make such a rash decision.

1 Macho Man

Just so we are clear, none of us know if any of these longstanding rumors are true. Regardless of what Stephanie McMahon and Randy Savage did or did not do with each other, it is all up to speculation. As it has been said numerous times, the only people who will ever know for sure if these two slept together are the two parties involved; one of them is dead and the other isn't spilling the beans any time soon. However, it's hard not to think that Vince McMahon probably feels a little embarrassed by the rumors. Even if he knows for a fact that nothing happened between Macho Man and his daughter, these are still some damning allegations against his little princess. Allegations that he wishes would just go away. Surely, he has to hate the fact that the theory is even being debated and has been debated among the wrestling community for as long as it has.


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15 Times The Billion Dollar Princess Embarrassed Vince McMahon