Anyone who’s ever watched any Vince McMahon segment in the history of wrestling has probably thought about how strange of a boss he must be. While he wasn’t always the most bombastic character in WWE history, the longer time went on, the stranger and stranger he became.
Everyone has their own favorite era of Vince McMahon, but many tend to agree that he was at his absolute zaniest in the 90s and early 2000s. Always with a flair for theatrics, it was and often is the case that when Vince McMahon shows up, WWE television becomes must-see TV. With countless incredible moments throughout his career, some make him one of the strongest bosses of all time.
10 That Time He Blew up
When most people think of wrestling, they probably don’t think about explosions, but Vince McMahon isn’t most people. On an episode of Raw back in 2007, Vince seemingly wanted to write himself off of television by killing the Vince McMahon character in a fiery explosion.
Unfortunately, real-life tragedies would cut the storyline short, so wrestling fans never got to see just what would have happened after the apparent death of Vince McMahon. Knowing what the writing was like back then, it’s almost impossible to guess what would have come after.
9 Those Times He Got His Butt Kissed
While some people try to kiss up to their bosses in order to get ahead at their companies, most people never have to do it literally. Vince has never been a man to spare anyone from moments of embarrassment, and as such, forced some wrestlers to kiss his butt on live television.
It wasn’t just a random thing either, the entire thing was referred to as, “joining the kiss my *** club” something that some surprising names went through with. Probably the most famous instance was when William Regal had to become a member of that very club.
8 That Time He Kissed Butt
Most people would probably assume that most big bosses wouldn’t subject themselves to the ridicule that those under them face, but to give Vince credit, he’s taken part in plenty of personally embarrassing moments. In fact, most of those moments are famous moments in WWE history.
Vince McMahon’s club became his own undoing when The Rock got his hands on the chaotic boss. Rather than The Rock forcing Vince to give him a peck on the cheeks, he had bigger things in mind. Bringing Rikishi out, Vince ended up with one stinky face by the end of the segment.
7 That Time He Was Attacked In A Hospital
On an episode of Raw in the late nineties, Vince McMahon found himself indisposed in a hospital. Rather than being left alone, the WWE talent had other things in mind, namely, Stone Cold Steve Austin. When Austin showed up, one of the most memorable, but strange WWE segments of all time was born.
Most people probably wouldn't want to show kids a man being assaulted in a hospital, but the late nineties were a different time. The boss of WWE was beaten while lying helpless in a hospital bed and screamed as Austin punched his injured leg.
6 All Those Times He Kissed The Female Talent
For one reason or another, Vince McMahon often found himself in situations with some of the most beautiful female talent that the WWE had to offer. Being the strangest boss in the world, he would often end up in some kind of entanglement with one of the women.
While the married man found himself kissing plenty of women, one of the most notorious moments was when he openly made out with Trish Stratus in front of his wife. It’s the kind of thing that only someone like Vince McMahon could get away with.
5 That Time With The Exotic Dance
Anyone who has ever seen the most famous Vince McMahon meme of all time should know exactly where that meme came from. It originates from a segment that Vince had with Stacy Keibler in which she seductively dances for the irate boss.
Vince puts on the performance of a lifetime as he reacts to the beautiful women dancing in front of him. At one point, Vince even falls clean out of his chair. The whole thing is bizarre, but there probably aren't many people who can make it through the segment without laughing at just how over-the-top Vince is.
4 That Time He Got A Beer Bath
The huge feud between Stone Cold Steve Austin and Vince McMahon had countless memorable moments, but one of the best was when Austin decided to give Shane, Vince, and even The Rock a beer bath. Watching each man get blasted by the hose is a sight most people can probably still remember without even seeing it.
As everyone progressively gets more and more soaked, Vince takes to the mat and attempts to swim out of the ring. It’s a strange moment, but one that saw everyone involved at the absolute peak of their performing days.
3 That One Time When He Boogied Down
Most people’s bosses only end up singing and dancing after a few too many drinks during a company night out at karaoke. Vince didn’t need any help to perform, because he willingly took to the stage during the Slammy Awards back in 1987 to perform an entire song.
The whole performance is exactly what any wrestling fan would expect, but it’s well worth a viewing. Even stranger, it’s not all that bad. It’s a bit cringe-worthy, but Vince gives the performance his all and even participates in a bit of a choreographed dance.
2 That Time He Got Shaved At Wrestlemania
Often referred to as the Battle of the Billionaires, Vince McMahon was at odds with none other than Donald Trump at Wrestlemania 23. It’s possible Vince just needed a haircut, but he really got his head shaved at the biggest wrestling event of the year.
In classic Vince fashion, he screams and cries during the entire thing only adding to how good the moment is. Anyone who has ever dreamed of shaving their own boss's head probably felt some catharsis from watching the whole strange thing go down.
1 That Time It Was Vince All Along
Anyone could argue as to what the most famous Vince McMahon moment of all time is, but many seem to agree that it was his reveal that he was The Greater Power during a particularly infamous storyline. Rather than trying to be a hero, Vince was always at his best at his worst.
Wrestling is filled with strange promos, but Vince puts all of his energy into proclaiming how he had the entire world fooled. Vince involving himself in storylines as the boss is one thing, but constant shrieking and yelling about his evil genius is something that will never not be strange, even if it is kind of great.