Of all the gigantic, larger-than-life superstars populating the WWE Universe, since the very beginning, one name has been bigger and more powerful than all the others: McMahon. Granted, that has more to do with the said name appearing on all the paychecks than anything else. At the same time, however, Vince McMahon is indeed a beast of a human, working out constantly and maintaining an incredible physique into his 70s. He’s also an absolute genius when it comes to marketing and management, but this hasn’t stopped Vince from occasionally embarrassing the hell out of himself -- and inside one of his own wrestling rings at that.

For every game-changing decision or shocking twist for which Vince is responsible, there’s another moment where he basically wound up in tears, begging for his own life. These moments have largely been scripted, of course, yet the cathartic feelings experienced by fans witnessing a wrestler give their boss what he had coming for him is entirely real. Each time Vince was left a defeated mess in the ring, the crowd just loved it, screaming their lungs out and wishing it were their own employer left a blubbering mess.

Why does McMahon continually book himself into scenarios where he’s made to look a fool? Believe it or not, the man simply understands what makes his crowds happy sometimes and is willing to give it to them every once in a while. There’s also the fact that when Vince isn’t crying or getting his butt kicked, he’s totally in charge of the sports entertainment industry, and it’s not like playing weak and pathetic now and again has done anything to change that. To examine both sides of this dichotomy, keep reading for 8 times Vince McMahon embarrassed himself in the ring and 7 times he actually looked like a boss.

EMBARRASSED HIMSELF: Blowing Out His Knees At The Royal Rumble

Virtually every wrestler has been badly injured at one point or another throughout his or her career. Injuries big and small happen in the industry almost every week, and for this reason, wrestlers shouldn’t be mocked for getting hurt. Generally speaking, insulting someone for getting hurt is a pretty low thing to do, inside or outside of the wrestling ring. All that said, when Vince McMahon managed to blow out both of his knees while simply entering the ring at the 2005 Royal Rumble, fans couldn’t help themselves from laughing. It was irony to the greatest degree—no one should have more experience getting in and out of a ring, a move, by the way, which has never once injured another living human being. And yet, Vince somehow managed to completely immobilize himself when sliding towards Batista and John Cena to make a decision about which one of them fell out of the ring first. The fact Vince recovered pretty quickly further made it easier to laugh at his pain.

LOOKED LIKE A BOSS: The Initial Match Against Steve Austin

Believe it or not, it wasn’t until Vince McMahon was the owner of WWE for over 25 years that he first stepped into a wrestling ring to compete in an official match. Naturally, Vince started right at the top, challenging Steve Austin for the WWE Championship on the April 13, 1998 episode of Monday Night Raw. Initially, no one imagined the straight-laced suit-wearing executive stood any chance against the Texas Rattlesnake… until he took off his jacket and revealed his biceps were bigger than most of his employees, and the rest of his physique could match them.

Of course, Vince still wasn’t a trained athlete, and so it was assumed Austin would make short work of him, which is why Vince used his trademark cunning to make Dude Love attack Austin before the match truly began. While it was barely a contest in the traditional sense, Vince still came out on top in more ways than one. Not only did he embarrass Austin for once, but he also did the unthinkable and defeated WCW Monday Nitro in the ratings for the first time in some 84 weeks, simply by deciding to step into the ring and wrestle. Now that’s star power only a boss can possess.

EMBARRASSED HIMSELF: Bang 3:16

While Vince McMahon looked pretty strong in his first official standoff against “Stone Cold” Steve Austin, the exact opposite was true for the vast majority of their feud. The Rattlesnake was consistently able to get one up on the boss week after week throughout 1998, and worst of all, he was reigning as WWE Champion, so there was nothing Vince could do to punish him without ruining his programming. Finally, Austin lost the title at Break Down 1998, and when a new champion wasn’t crowned at Judgment Day with Austin as the guest referee, that meant Vince finally had cause to fire him. And he did, for one night. Unfortunately, the night after, Austin went full disgruntled employee, carrying a gun into the arena on Monday Night Raw and chasing Vince into the ring, forcing him to his knees and getting him to beg for his life while apologizing for the firing. For the capper, Austin pulled the trigger anyway, revealing it was a fake gun that read “Bang 3:16.” Of course, he didn’t give away the joke until after Vince had peed his pants, truly one of his lowest, most embarrassing moments.

LOOKED LIKE A BOSS: Winning The WWE Championship

Nothing spells success in the wrestling business like winning the WWE Championship. Perhaps, it was knowing this fact that inspired Vince to write a story that ended in him walking away with the gold against all odds. The moment happened in late 1999 on an episode of the then still brand new SmackDown, which saw Vince defeat Triple H for the gold with unlikely help from Steve Austin and his son Shane McMahon, the contest’s referee. Truth be told, Vince didn’t look all that corporate winning the gold, needing Austin to drag his unconscious body against his son-in-law’s, but the real glory came the next Monday on Raw. Proudly donning his belt against his shoulder, McMahon walked to the ring for his one speech as WWE Champion, in which he promptly vacated the belt. The whole saga has received some controversy, with some fans asking if McMahon really deserved the honor, considering how rarely he wrestled. On the other hand, nothing made it more clear just how much power Vince had than making himself his own top star.

EMBARRASSED HIMSELF: Mocking Jim Ross

In most cases, the ways Vince McMahon embarrassed himself were entirely justified by the extent to which his audience enjoyed watching him do it. In fact, that’s usually the entire point, with Vince crafting his own embarrassment from beginning to end solely to achieve this end. Other times, however, no one knows what the hell he was trying to do, an issue that can be confusing in and of itself. Throw in the unnecessary mockery of one of his most loyal employees, and it goes from bizarre to downright shameful.

This trend is never worse than in the various segments where McMahon has attempted to mock or belittle Jim Ross, insulting the legendary announcer for sins like having Bell’s palsy or needing a week off for colon surgery. These are the sort of issue no employer should ever degrade his or her talents for, and yet Vince clearly took such glee in doing so, he just couldn’t stop for a while. In many respects, anytime Vince tried to insult JR is more embarrassing than peeing his pants on purpose or any other silly thing he did in the ring since it was entirely out of pettiness, and everyone knows it.

LOOKED LIKE A BOSS: Introducing WrestleMania III

For over two decades, it looked like the pinnacle of WWE would forever be WrestleMania III, an event where an alleged 93,000 fans witnessed Hulk Hogan defend the WWE Championship against the “undefeated” André the Giant. While the official story on what happened isn’t entirely true, it was indeed the biggest pro wrestling crowd in history until 2016, when 101,000 fans attended that year’s Showcase of Immortals. In any event, the moment relevant to this list had nothing to do with these inflated figures and was all about the man who organized the events. WrestleMania III ended with a bombastic leg drop, and the beginning was just as explosive, with Vince McMahon himself standing in the ring to welcome the crowd to the show. Triumphant barely begins to describe how McMahon looked, standing in front of more fans than any wrestling promotion had ever imagined would attend a single show, proving once and for all he had conquered the industry.

EMBARRASSED HIMSELF: Vince Is The Higher Power

Although no one person has achieved greater success in pro wrestling than Vince McMahon, this doesn’t mean every single thing he’s done on camera was necessarily a hit. To the contrary, Vince has created as much horrible television as he has true entertainment, and in the worst-case scenarios, he was solely responsible for just how awful his programming was. Arguably, the creative nadir of Vince’s character came in the midst of his highest-rated and most-watched time period, the Attitude Era, compounding the failure through how many people were watching. The horrible mistake his character made? Revealing himself as “The Higher Power” pulling the strings of the Corporate Ministry, a move that made absolutely no sense to anyone watching. Throughout the Corporate Ministry’s existence, Vince was one of their greatest rivals, and thus, making himself their leader was proof positive his company had no idea where they were going with the story. That it basically fizzled out from there further proved this fact, turning it into a truly embarrassing scenario all around.

LOOKED LIKE A BOSS: Getting Steve Austin To Sell His Soul

This next one is going to be a little bit controversial, as some people believe the moment in question was a serious misfire that greatly damaged WWE’s standing pretty much indefinitely. On the other hand, from a character perspective, Vince McMahon rarely looked so powerful than in the ending moments of WrestleMania X7, when he finally made “Stone Cold” Steve Austin turn to the dark side and start doing his bidding. Several of the most embarrassing moments this list covered were cases of Austin outsmarting McMahon, and for him to make his arch-rival basically realize he couldn’t beat him and thus decide to join him was the greatest victory he could ever imagine. Earlier in the night, McMahon had been defeated by his own son Shane in an epic street fight, leaving Vince looking a little haggard and exhausted from the start. Even so, his handshake with Austin was a moment of pure triumph for McMahon, one where he once again proved to the world he had full control over every last piece of his WWE empire.

EMBARRASSED HIMSELF: The Saga of His Illegitimate Son

In all fairness to Vince McMahon, half the time he embarrassed himself inside the wrestling ring, that was the whole point. As already explained in the whole "peeing his pants" incident, fans liked watching McMahon get his comeuppance, wishing it was their own boss going through the torment he suffered. Other times, however, there was no silver lining to why Vince made a fool of himself, as no one was laughing; nor did they want to see whatever it was that made him feel so ashamed. One instance was the long saga of his illegitimate son, and especially the payoff that said secret love child had been WWE’s favorite leprechaun, Hornswoggle. For some reason, the fact McMahon didn’t know that the diminutive, mischievous former WWE Cruiserweight Champion was his son was supposed to be embarrassing in and of itself, hence Triple H laughing hysterically upon delivering the news. The way most fans saw it, though, was that the idea was boring, senseless, and not at all embarrassing, except insofar as how WWE expecting this angle deserved main-event spotlight proved they were totally clueless about how to make an entertaining wrestling show.

LOOKED LIKE A BOSS: Telling Mark Yeaton To Ring The Bell

This next entry is another one that some WWE fans, especially fans of Bret “The Hitman” Hart, are going to find a bit questionable. Before we get ahead of ourselves, let’s be clear and say this isn’t necessarily a defense of Vince McMahon’s actions in the Montreal Screwjob, where he conspired to have Shawn Michaels win the WWE Championship from Hart without the latter’s knowledge. However, in doing so, Vince was making it absolutely clear to the Hitman, his fans, and everyone else in the wrestling world, exactly who it was who ran the show. Not only did Vince force HBK and referee Earl Hebner to help him screw Hart over, but he also walked down to the ring in his trademark strut and watched it go down up close in personal. To make extra sure Hart knew who was in charge of the double cross, McMahon also screamed at the timekeeper, Mark Yeaton, to “ring the ----ing bell” before Earl Hebner even gave him the order. While none of this made McMahon look like a boss we’d want to work for, it definitely proved he was the man in control of his company.

EMBARRASSED HIMSELF: Forcing Female Employees To Make Out With Him

In the warped minds of some men who believe that any time they kiss a beautiful woman, they've somehow “won,” this could easily wind up on the other half of this list. However, to a more evolved mind, the fact Vince McMahon has instructed a good half dozen female employees to vigorously make out with him on camera simply due to how much power he possesses says something a bit less flattering about his psychological state. Were these women genuinely attracted to Vince, perhaps there could be something said about his charisma, but the fact he’s essentially forcing them paints him as a weak man who needs to control women in order to feel important or powerful. Considering some of the women he’s made kiss him, like Torrie Wilson or Sable, clearly didn’t enjoy the experience, it gave their multiple liplocks a creepier edge, making them extra pathetic, knowing McMahon wanted so badly for the experience to happen that he demanded it.

LOOKED LIKE A BOSS: Plotting Against Hulk Hogan

Alright... so in some respects, the above picture might make it look like Vince McMahon is in a pretty desperate state. Taken from a screenshot of his WrestleMania XIX match against Hulk Hogan, Vince is indeed wearing the proverbial crimson mask, his face covered in blood spilled by the Hulkster’s hands. However, we’ve nonetheless chosen this exact moment as one of Vince’s most triumphant, due to how brilliantly directed it was. What the picture alone doesn’t capture is Vince slowly creeping up from behind the ring, wearing that trademark evil smile and holding a lead pipe. It was an expert piece of villainy -- a monster the hero thought had been vanquished slowly rising up from hell ready to unleash unearthly chaos. No, Vince didn’t look like a Fortune 500 CEO in this instance, but he did look like the meanest, most vicious wrestler alive, a status he’s no doubt secretly wanted all along.

EMBARRASSED HIMSELF: Making Trish Stratus Bark Like A Dog

As if it wasn’t bad enough for Vince to instruct half of his female employees to lock lips with him on camera, he really took the misogynistic sexism to another level during what was probably his longest-lasting onscreen relationship. No, we’re not talking about his ongoing, 50+ year marriage to his wife, Linda, but instead, the heated dalliance he shared with future WWE Hall of Famer Trish Stratus. One early 2001 evening, Vince called Stratus, then his secretary/mistress, and forced her to beg for her job after failing him for the last time. When her words alone didn’t do the trick, McMahon had Stratus strip to her underwear, get on all fours, and crawl around the ring while barking like a dog. The whole thing was degrading, demoralizing, and disgusting, especially given his status as the poor woman’s actual, real-life boss. While the point was to make fans hate McMahon’s character for being a jerk, what actually happened was people believed he was an actual, real-life misogynist, a move that later even affected his wife’s multiple Senate campaigns.

LOOKED LIKE A BOSS: Announcing He Purchased WCW

Easily the most triumphant moment of Vince McMahon’s career occurred during the opening segment of the March 26, 2001 episode of Monday Night Raw. For the first time ever, WWE fans saw a glimpse of WCW Monday Nitro, slowly panning over to a smiling Vince McMahon, who announced to the world that he had purchased his competition after a six-year war. Both in character and to the real Vince McMahon, this had been his primary goal from the minute Ted Turner called him up and said he was looking to get in the ‘rasslin business.

As Eric Bischoff started to intensify the war, Vince’s fervor for complete annihilation of his opponents grew ever stronger, and he wore his emotions on his sleeves while delivering his victory speech. Beaming with pride, Vince bragged that WCW performers who betrayed him, like Jeff Jarrett, would be gone forever, and those who were loyal would be rewarded. Though Shane swooped in at the end of the night and one-upped his dad in the storyline, in reality, Vince’s had indeed won the war, and his triumphant victory speech was a declaration that he once again owned all of mainstream wrestling.

EMBARRASSED HIMSELF: The Kiss-My-Ass Club

And so, the egomania of Vince McMahon has come to this. Far more embarrassing than peeing his pants, outing himself as a creepy sexist, or breaking both his legs while sliding inside a wrestling ring combined were the not one, not two, but five damn times Vince McMahon willingly dropped his pants and bent over in front of wrestlers, demanding they literally kiss his bare ass. The worst thing about it was that in Vince’s own mind, these were moments of triumph. He’s Vince McMahon, damn it, and that meant he had total control over even his most rebellious employees. They dared defy him, so they had to prove their submission by groveling and brown-nosing to a literal degree!

Unfortunately for Vince, no one else saw it that way, instead seeing a disgusting old pervert forcing his staff to perform quasi-sexual acts for his own pleasure. The crowd didn’t cheer or boo any of the times Vince asked an employee to pucker up; they simply recoiled in disgust and hoped it was all over.

Source: WWE