Vince McMahon is often heralded and praised by people for the impact that he has made on the professional wrestling industry as a whole, and there is no doubt that he is a creative genius. However, there are also plenty of times that Vince has crossed the line both in business and personally.
On-screen and behind the scenes there have been moments where the WWE Chairman has been slightly creepy, which is something that a lot of fans can forget about at times. It's always strange to see Vince in certain situations that he books himself into, as it leaves fans questioning what is happening in front of them.
10 Kiss My Ass Club
Anytime something to do with nudity is suggested by Vince McMahon it instantly gets a little creepy, even when it is at his expense, like the Kiss My Ass club was. He was the one exposing himself to the world, which is likely how he justified it, but he was still making his employees kiss his rear end.
It was an odd time in professional wrestling and it created a strange gimmick that few people enjoyed. There ended up being several of these segments over months, but it isn't an angle fans look back upon with overly fond memories.
9 An Incest Angle
Not everything that Vince McMahon pitches in wrestling ends up happening on television, and that is a good thing because some of his ideas are not good. When Stephanie McMahon got pregnant, Vince suggested an incest angle that would have seen him be the father.
This was then changed to Shane being the father, both of which ended up being shot down for obvious reasons. But, it showcased a creepy moment from Vince's past which is something that fans will be pleased didn't see the light of day.
8 Booking The Live Celebration
The live sex celebration is a famous segment from WWE's history, and it is one that people still remember, but that doesn't mean it wasn't creepy of Vince McMahon to book it. There are very few jobs where a boss can even suggest that idea, let alone make it happen on national television, live in front of a crowd.
The fact that Lita has since come out and admitted the entire thing made her feel uncomfortable doesn't help matters with this one either. It wasn't a great idea for it to be booked, and in today's modern era is something that would likely not be allowed.
7 Vince's Devils
Vince's Devils is a forgotten faction by most wrestling fans and with good reason, as it had little to no impact. This was seemingly done to just put three attractive wrestlers with Vince wearing revealing outfits that would occasionally end up making out, for some reason.
The group didn't have any real bearing on Vince or what he was doing, and in terms of storyline, they barely received anything. If there has been some rhyme or reason for the faction existing it might have been worth it, but that wasn't the case and instead, it felt rather creepy.
6 Making Trish Bark
This moment was done to get heat onto Vince McMahon for how he would bully and manipulate talent in the storyline, but making Trish Stratus act like a dog was a step too far. It was devaluing to Trish at the time and made her look poor, which is a shame considering how talented she is as a worker.
It was also creepy that Vince marked her get undressed to her underwear in this segment, which was a ridiculous moment to add into an already bad wrestling segment that Trish shouldn't have been put into in the first place.
5 Wrestling His Daughter
Certain matches just don't need to be booked, and Vince McMahon facing Stephanie McMahon was one of them. He went too far in the match when it comes to violence, and while family fights, this is something that took it to the extreme.
It was only a storyline for people to enjoy and there were entertaining aspects of that, but it still went too far. It became creepy seeing him literally beat up his daughter, and while it is wrestling so it's not all real, there were still aspects that were uncomfortable to watch.
4 Natalya's Farting Gimmick
Vince McMahon is ultimately the one who has the final say on everything that happens on his product, which includes all of the gimmicks that end up making it to television. That includes the dreadful Natalya character that saw her passing wind regularly.
It was a creepy idea to create, and was a gimmick that nobody ever cared for. This wasn't something that was going to take Natalya to the next level, and all it served was to embarrass her regularly which was a strange idea for him to make.
3 Love Of Puke
Vince McMahon is a fan of lots of strange humor, which includes people being sick, and that is something that he has wanted to create a gimmick of someone doing just that. The famous video of him on the "Beyond The Mat" video showed him pushing Droz while yelling, "he's gonna puke."
It was a creepy idea to be so obsessed with, and that is something that he has pushed several times with one-off moments over the years, proving that this is an idea he's never going to give up on.
2 Segment With Stacey Keibler
Stacey Keibler was often booked into romantic segments during her time in WWE, but they weren't always with the boss. However, when Vince McMahon was looking for a new assistant, he ended up in an odd segment that saw Keibler dancing inappropriately for him to try and win the job.
Considering he was her literal boss, it made very this feel strange to watch from a fan's perspective given that so many women have been pressured into jobs in real life, with this being a strange situation for him to book.
1 Vince Kissing Talent
The creepiest thing that Vince McMahon has done is book himself to kiss some of the female talents in the company. That is something that a boss should never do, as there was never a need for him to be in that position. While romantic storylines in wrestling can work, Vince shouldn't have been involved in any.
The position of power that he had meant that him taking on that role instantly felt very creepy and shouldn't have taken place. It was always awkward to watch from a fan perspective as well, which didn't make Vince look good.