Guys with money and power tend to be massive sleazebags. Think about it. Think of some of the richest men in history. More than likely, whoever you thought of may have been a pervert, a serial killer, an unintelligible git, or just flat out creepy. Take a billionaire like Vince McMahon, for example. The guy has taken a multi-million dollar corporation and turned it into an unbreakable empire. A small boy whose upbringing started in the confines of a trailer grew up to rise through the ranks of Titan Towers. He then proceeded to dominate the wrestling world with an iron fist both behind and in front of the camera. Behind the camera, Vince crushed his competition, raised his stocks, compiled stacks of money, and made connections with the right people now stretching to as far as the White House. In front of the camera, he played the diabolically evil megalomaniac that is Mr. McMahon. In his on-screen persona, Mr. McMahon has proven to be selfish, egotistical, untrustworthy, two-faced, vindictive, and of course, creepy. In more ways than one, Vince McMahon and Mr. McMahon aren't too different.
Both the character and the man behind the madman have been accused of abusing their power and taking advantage of opportunities that they never deserved in the first place. Both the man and the character have also made questionable business decisions that allowed audiences to paint McMahon in a questionable light. For these reasons and more, Vince McMahon himself has been considered to be selfish, egotistical, untrustworthy, two-faced, vindictive, and yes, just like the persona which he portrays on television, creepy. Life has imitated art (and vice versa) so many times with Vince McMahon that it's sometimes hard to separate the character from the person. So we're going to discuss the real-life events (and allegations) concerning The Chairman, as well as the dastardly deeds that the character has committed on-screen, to talk about just how creepy of a guy Vince McMahon can be sometimes.
15 Making Trish Bark Like A Dog
When thinking of this now infamous segment from the March 5th, 2001 episode of Monday Night RAW, a lot of adjectives can be applied to Mr. McMahon and his role in this segment: jerk, bully, pervert, etc. But above all else, whether you look at this from a kayfabe standpoint or a real-life one, Vince is just creepy in this case. In kayfabe, it's creepy for a maniacally evil boss to punish his mistress to strip down to her undergarments in front of a live audience. In terms of real life, there's something unsettling about a businessman who runs a million-dollar corporation not only booking himself to liplock with every woman who walks into his company but also booking one of them to be humiliated and sexually demeaned on live television. Though it's even more disturbing that the live crowd actively cheered this on when they were supposed to sympathize with Trish Stratus, it's almost creepier that Vince booked this, to begin with.
14 The Kiss My Ass Club
The Kiss My Ass Club was formulated by Mr. McMahon on the episode of RAW following Survivor Series 2001 as the ultimate power move. It started with William Regal, the Gentleman Villain being told that the only way to keep his job after betraying the company to join The Alliance was to kiss Vince's derriere. Other members that would come in later years would be Shawn Michaels, Mick Foley, and Jim Ross. Every time, Vince McMahon would gleefully cackle as his employees puckered their lips for his butt cheek. In kayfabe, it's a great heel tactic that fits the over-the-top Mr. McMahon character to a tee. In real life terms, it's a little disrespectful for Vince to repay his employees for their hard work by booking them to kiss his butt. Either way, it's outright creepy that Vince is making grown men kiss his butt in front of a live audience.
13 His McMahon Documentary
For a WWE-produced special, the 2006 McMahon documentary is a surprisingly candid (if not slightly embellished) and always fascinating piece on the McMahon family, although some aspects of the doc make the family out to be a rather kooky and creepy cast of characters, namely, the segment where it was explained that Vince had tried to convince his daughter, Stephanie, to let him be the on-screen father of the real-life child she was pregnant with at the time. Not surprisingly, Stephanie refused. As if that weren't gross enough, Vince tried to persuade his daughter into agreeing to this wacky incest angle further by pitching for the father to be her brother, Shane. Also not surprising, she again declined until Vince dropped the whole incest thing completely. Though he would eventually get his incest wish by booking for siblings Paul and Katie Lea Burchill to allude to being incestual with each other, that pairing from 2008 flopped terribly.
12 His Lapdance From Stacy Keibler
During some moments in WWE, it's clear as a viewer that the segment was made to stroke Vince's ego. Other times, it's clear that the segment is supposed to just stroke Vince PERIOD. In this case, it was both. During a 2002 episode of SmackDown, Vince got in front of the live crowd to hold interviews for a personal assistant. The first interviewee was just a bland guy. The next was an older woman whom Vince nearly hired because she promised to take "great dictation," among other personal favors. And the third interview was with Stacy Keibler, who lacked a proper resume, but had long legs, so Vince obviously loved her. To seal the deal, she gave The Chairman a lapdance and was made into his new assistant. It seemed like this segment achieved nothing but to give Vince a reason to get some Diva action without cheating while also simultaneously supplying entertaining television.
11 Booking Himself To Smooch All The Divas
One of the more unsettling aspects of Vince McMahon is how frequently he books himself into romantic angles with the women of WWE. Never mind the fact that he's already married in real life. What's most bothersome about how often Vince would book himself to feel up on or straight up make out with WWE Divas is the fact that it quickly turned into the norm in WWE once upon a time ago as if any female wrestler who signed for the company needed to expect that they would one day eventually entertain the advances of Vince McMahon. The list of female employees who fooled around with Vince seems endless. Trish Stratus, Melina, Sable, Torrie Wilson, Candice Michelle, etc. The list seems endless, and for the most part, it was blatantly obvious that Vince only booked himself in such segments so that he could stroke his ego that such beautiful women would even want to get with an old fart like him. And, of course, so he could get away with these women stroking something else of his without it being considered cheating on his wife.
10 Vince's Devils
In most of the instances where Vince booked himself in on-screen angles with women, there was at least some kind of satisfying storyline involved which made sense by the end of it. Trish being Vince's mistress only to be betrayed made sense and worked because Trish was able to get comeuppance and revenge against Vince afterward, making the angle worth it. Even with Sable and Torrie Wilson's vying for the affections of Vince, it can be argued that it was able to tie into Sable and Torrie's feud/pseudo-lesbian angle. As for Candice Michelle's affiliation with Vince upon joining the stable dedicated to him, Vince's Devils? Not so much. There were several segments that occurred on RAW on a weekly basis where Vince and Candice would make out for generally no reason. There was no storyline payoff afterward, and, to be honest, there was no storyline. It was just another case of the creepy boss booking himself to make out with another Playboy centerfold.
9 Sexual Harassment Allegations
Over the years, there have been a number of sexual harassment allegations against Vince McMahon. None of the stories have been confirmed, and he's never been convicted on any allegation, but even a handful of allegations is too many, and it's disheartening to think he may have committed such crimes. One allegation came in 2006 when a tanning salon employee claimed that Vince harassed her while on the job. A police report was filed on the day of that year's Royal Rumble, but no charges were made against The Chairman. Another allegation comes from wrestling legend Kamala, who, in an interview with 1Wrestling Radio, claimed that the key to success in WWE was doing sexual favors for Vince McMahon. And since Kamala failed to do any of those favors, his WWE career was a flop. Keep in mind that no former or current male wrestlers have come forward to back up Kamala's claims. Kamala himself went on to refute his claims in a 2014 Bleacher Report interview, claiming that his attitude was what hindered his own career. Vince's biggest allegations against him came from former female referee Rita Chatterton.
8 Dropping the N-Word
Vince McMahon has always aired some weird stuff on his programming for the sake of a laugh. Whether it be Mark Henry shagging up with a transsexual or birthing a hand with Mae Young, Vince has proven to have an odd sense of humor. He's also proven to have a wildly inappropriate sense of humor, as made evident during the Survivor Series 2005 pay-per-view. In one segment, John Cena -- who was still showing signs of his former rapper character -- ran into Vince McMahon, who congratulated the WWE Champion on the work he's put in thus far and told him to "keep it up, my n*gga!" Adding salt to the wound, Vince walked past an appalled Booker T and his wife, Sharmell. Many viewers were incredibly offended, so much so that the segment resurfaced in 2015 in light of Hulk Hogan's own racist remarks. Critics were especially disturbed with how Vince gleefully said the word with ease without any self-awareness of the hatred behind that word -- definitely not a segment for the PC crowd.
7 His 2003 Feud Against Stephanie McMahon
There aren't many things more disturbing than watching a father beat up his own flesh and blood. Vince McMahon did this towards Stephanie McMahon for the better part of 2003's Smackdown programming. When the WWE Chairman came to a dispute with the then-SmackDown General Manager, Vince didn't want to fire Stephanie. Instead, he wanted to convince her to quit by pitting her in wrestling matches with behemoths like Brock Lesnar and A-Train. Stephanie refused to quit, so he booked her in one final match: an I Quit match against none other than Vince himself. For an uncomfortable 10 minutes at No Mercy, a father abused his daughter in front of a stunned audience. Still, Stephanie refused to quit. The match didn't end until Linda McMahon had to throw in the towel for her daughter.
6 The Brian Pillman Interview
One of the most uncomfortable moments in RAW history (and, frankly, all of WWE history) came on the October 6th, 1997 episode, which was done in tribute to the late Brian Pillman. Pillman had just passed due to a pre-existing (but undetected) heart condition, but there was speculation from the media that his heart attack had more to do with his wrestling profession (i.e. drugs, steroids, stress of the job, injuries, etc.). So to clear the air about it all and basically get some heat off his back, Vince McMahon interviewed his wife, Melanie, just 24 hours after her husband had passed. It was uncomfortable viewing to see an obviously still grieving and distraught woman in tears be forced to discuss early details about her husband's death. It was completely tasteless on Vince McMahon's behalf and a shameful leap of misjudgment from him.
5 Rita Chatterton Allegations
In the mid-80s, WWE hired its first female referee, and her name was Rita Chatterton. She'd leave the company by the early 90s, but in 1992, she dropped a shocking bombshell on Geraldo Rivera's Now It Can Be Told talk show. Chatterton claimed that Vince McMahon had sexually assaulted her after she had refused to give him oral sex inside of his limousine. She then alleged that Linda McMahon had actually paid her off $5 million in "hush" money to keep quiet. No formal charges would be made by Chatterton against Vince, but Vince did sue Rivera for conspiring with Chatterton to make false allegations against him. Then, in 2010, Vince’s attorney threatened legal action against anyone who published these accusations.
4 His Howard Stern Interview
It's a rare thing to see Vince McMahon do an interview with anybody. We should assume that this isn't because he doesn't like interviews but because he always feels compelled to be 100% brutally honest. Given his line of work and reputation, he probably realized a long time ago that he shouldn't be so forward with interviewers, but despite all of the controversies and eccentricities regarding his life, he always comes off as completely honest, even to a fault. Take his interview with Howard Stern, for example, where he spoke truthfully about having cheated on his wife, Linda, numerous times. At the time of the interview, he claimed that he hadn't cheated on her in 6 years, that she knew about all of his affairs, and that they left it all in the past. The main reason why this is creepy is because of all those sexual harassment allegations that have popped up against Vince over the years, especially those claiming Linda paid certain parties off to hush up. If the longstanding cheating rumors are true, it makes us wonder if any of those harassment allegations are true as well.
3 His Playboy Interview
As his interview with Howard Stern would suggest, Vince McMahon is open to talking candidly regarding just about anything in his life. Though he tends to keep his home life private for the most part, compared to his life in the public eye, he doesn't shy away from the juicy bits about his life. His 2001 interview with Playboy Magazine puts heavy emphasis on that suggestion. In the interview, Vince talks openly about (among other things) his physically abusive father, his sexually abusive mother, and how his stepfather married Vince's cousin. Believe it or not, none of that is the creepiest thing that Vince said in the interview. That would be how Vince had somewhat of an affair with said cousin and how the two frolicked naked together in the woods. But wait! That still isn't the creepiest part of the story! The creepiest part is how Vince said he wanted to put crushed leaves in the girl. He didn't know why, but he did.
2 Booking Himself Against God
Fans have always been of the opinion that Vince McMahon would go to any and all lengths to make his Mr. McMahon character come off as sleazy as possible, but he took that notion to new heights in 2006. In the fallout to WrestleMania 22, after Vince was brutalized in a Street Fight at the hands of Shawn Michaels, Vince decided to test The Heartbreak Kid's faith in the good Lord above. For the upcoming Backlash pay-per-view, Vince made a tag team match between himself and "the product of [his] semen," Shane McMahon (the fact he called his son that is the creepiest part about this whole thing) against HBK and God. Yes, that God. Unsurprisingly, with assistance from The Spirit Squad and no one for Michaels to tag in, it was essentially a Handicap match that McMahon won, meaning, in the record books, Vince McMahon has a win over God. What makes this creepy is that it made us wonder just what depths Vince was willing to go if he was willing to put himself over against God. The thought that he may have no limits is kind of scary.
1 A-- Cream
January 21st, 2008 was a special night for WWE as it was the very first episode of Monday Night RAW to be presented in high definition. Mr. McMahon wasted no time to make full use of the remarkable new television quality: just a couple weeks later, on the February 4th episode of RAW, Vince McMahon decided to showcase his bare buttocks for the world to see in crystal-clear high definition. The episode was promoted on the basis of Vince McMahon making an example of his illegitimate son and resident company leprechaun, Hornswoggle, by forcing the little b*stard to join Vince's exclusive Kiss My Ass Club. To prepare for the occasion, earlier in the night, we saw a segment where Vince got his butt buffed by a dubbed "professional ass buffer," using an electric buffer to shine The Chairman's cheeks. To top it all off, Vince asked if the buffer "brought the ass cream" before the buffer used said cream to shine Vince even further. Afterward, Vince was ecstatic at the thought of his ass in HD. It's creepy enough to be hellbent on getting his supposed son to literally kiss his ass, but to pay a guy to lather his ass with ass cream is just plain weird.