The 20 Most Embarrassing McMahon Family Moments

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There’s nothing quite like professional wrestling. It’s a remarkable mix of athletics and theatrics that, when sewn together, become a spectacle unlike any other. At the heart of it all, one can say pro wrestling is a show and that its stories are character-driven. One can also say that WWE is the biggest and best at bringing out these dramatic scenes to a global audience.

The WWE skyrocketed into a household name - if it wasn’t already - by the late 1990s, based largely around the idea that the owner of the company, Vince McMahon, and his eccentric family, were becoming characters on the show. And what characters they would become! They would more-often-than-not be the hated power-holders who would meddle with the wrestling stars' affairs in order to insure their interests were met.

However, when you try to stick your nose into the business of men and women who fight each other daily for a living, no matter how powerful you may be, you’re going to get burned. With that said, the McMahon family has certainly had their fair share of moments that they would absolutely like to forget.

Here’s a list of some of the McMahon family’s most embarrassing moments.

20. Steve Austin Destroys Vince’s Car

Show of hands: how many times have you hijacked a cement truck and made your boss watch, in absolute horror, as you turned his $50,000 Corvette into a big, wet brick on prime-time national television?

I’d imagine not too many hands went up there. However, that’s exactly what Stone Cold did to get back an overbearing and vindictive Vince McMahon. Oh, what a life it would be to be Steve Austin!

19. Comatose Linda Gets Cheated On

If you’ve been watching WWE for years, more specifically Vince and his family, you’d imagine there isn’t much they wouldn’t do to try to draw an eyeball for the all-important TV ratings. Arguably, that was never more evident than when Vince McMahon cheated on his wife Linda, who had been in a storyline comatose state, with Trish Stratus right in front of her!

The end result did see Vince ultimately get his comeuppance from Linda (and Shane), but you’d have to say that it was, by far, a more humiliating experience for Linda McMahon than it was for Vince.

18. Kurt Angle’s Milk Truck

After Stone Cold got himself disqualified against Kurt Angle in their title bout at Unforgiven 2001, Angle was upset, to say the least. So, the next night on Raw, when Stephanie McMahon rallied The Alliance for ‘Stone Cold Appreciation Night,’ Angle saw a perfect opportunity to get some revenge on them.

Kurt Angle interrupted Stone Cold mid-speech and came out driving a milk truck to a thunderous applause. He proceeded to lay waste to Alliance henchmen and then went on to, in a call back to Stone Cold’s beer truck moment, soak Stephanie, Austin, and the rest of The Alliance with milk in the middle of the ring. This left Stephanie McMahon humiliated, with Jim Ross delivering the incredibly memorable line: “the Million Dollar Princess has just become the Dairy Queen!”

17. Shane Buys WCW

Around the turn of the millennium, something happened that would forever change the landscape of Professional Wrestling: Vince McMahon’s WWE drove Ted Turner’s WCW out of business.

With the demise of WCW, it was affordable for Vince McMahon to purchase the company outright. He got everything that ever belonged to them, and with that, was ecstatic that he had finally put an end to his biggest domestic, arguably global, competitor. So much so that he decided to make an event of it by showing live broadcast clips of WCW’s last ever episode of Nitro.

At the end of the night, just when Vince was about to make the big reveal that it was he who had purchased WCW, his son, Shane, interrupted to let him know that while the name on the contract did say “McMahon,” it said Shane McMahon. He had taken WCW’s ownership out from right under him and served a blow to Vince’s egomaniac character.

16. The Rock Cleans House

Heading into WrestleMania 2000’s Fatal Four-way main event for WWE Championship, every competitor was backed by a member of the McMahon family. The Rock, who was running and hot and whom many thought would come out the victory, was screwed over by his backer, Vince McMahon.

McMahon’s justification was seemingly to unite the family with Shane, Stephanie, and Triple H, with the latter as the family’s champion. The Rock did not take too kindly to being screwed over, as he went on to take out all of the members of the group; he left Stephanie last to take a Rock Bottom and a People’s Elbow in front of a rapturous crowd who felt like at least some justice was served.

15. Vince Blows Out Both His Quads

The 2005 Royal Rumble was a memorable one for many reasons. It had a solid roster of entrants and it ended with two of WWE’s hot, young, up-and-coming stars in John Cena and Batista. The ending itself was a thrilling double-elimination between Cena and Batista.

As the officials and the crowd were hotly debating whose feet had touched the ground last, an absolutely white-hot Vince McMahon came storming down to the ring to settle the issue at hand. However, perhaps Vince was too hot because he entered the ring from under the bottom rope and as he was getting up... he blew out both his quads!

It made for an odd scene, one we could look back at now with humor, as people just saw Vince sitting down as the officials and the wrestlers came to plead their cases of whom the victor was. Not one of Vince’s brightest moments.

14. Austin Rips Into Steph

Stephanie and Stone Cold definitely didn’t always see eye to eye. In fact, one time, I’m sure that was particularly difficult.

Back when Vince was too busy to run the show because he was a bit tied up with Trish Stratus, he let Stephanie take the reins for a bit. At this time, she had issues with Austin and figured she would use her authority to make him suffer. After Austin dumped beer on her on a few days earlier, Stephanie sought vengeance by making Austin work as a hot dog vendor. As the tension rose throughout the night between the two, it culminated with Austin putting the vendor’s tray on Stephanie to see what it would look like. Irate, she ordered him to remove it; as he did, he ripped off her shirt with it leaving the young McMahon topless in front of the entire arena.

She ran backstage, completely and utterly flustered.

13. DX Make Vince Kiss Big Show’s Butt

It’s never thrilling to have to be an “ass-kisser,” especially if you work in the WWE.

Vince McMahon famously had a group named the ‘Kiss My Ass Club,’ which was dedicated to people who have wronged him. Many times, if someone had crossed him, their punishment for reinstatement would be that they would have to kiss his bare butt in the middle of the ring, in front of the live audience on broadcast television. Members included the likes of William Regal and Jim Ross. It was completely humiliating.

So how sweet it must have been for them to see Vince, inside of a steel cage with nowhere to run to, have his head buried into the Big Show’s bare butt by Shawn Michael and Triple H at Unforgiven 2006.

12. Chris Jericho and The Rock Insult Stephanie

If you were to look back, you would see how many great moments Chris Jericho and Stephanie McMahon had in their rivalry. Filled with jokes that would land him the upper-hand, Jericho always got the better of Stephanie. That was until she had someone beat him up for it. One of the finer moments in their ongoing feud that was not short on entertainment happened to include The Rock.

In a segment where Chris Jericho and Stephanie were bantering in the ring, McMahon mentions that she hoped that The Rock would “clean his clock,” alluding to their upcoming match. The Rock made his entrance at this point and in no time, he and Jericho traded hilarious insults about Stephanie. This would be more than she could bear as she ran out of the ring and up the ramp screaming like a petulant child.

11. Stone Cold Stuns Entire McMahon Family

When the WWE brought Raw back to the USA Network in 2005 after a few years away with TNN/Spike TV, they wanted the first night of the return to be a big deal. As one would imagine, they pulled out a lot of stops to make the return episode an event worth watching.

The show was packed full with segments featuring WWE alumni and high-quality matches. The most memorable moment would come from, as it has so many times before, ‘Stone Cold’ Steve Austin. With the presence of all four members of the McMahon family that night, Austin did not want to waste the opportunity to drop a few Stunners on the people that always got in his way. Even the usually subdued and innocent Linda McMahon was ‘Stunned’ that night!

10. Stephanie Slaps Linda

WrestleMania 2000 season was a very tense time for the McMahon family. With tensions running high and dividing lines drawn, everyone was on edge. Even with all that, it was still quite the shocker when Stephanie smacked her own mother in the middle of the ring. Stephanie’s power-trip slap left a crumbled Linda in tears. This vilified the younger lady McMahon even more in the eyes of the audience. It was a disgusting act of disrespect.

Linda would eventually get the better of Stephanie by shoving her to the ground and out of her way so that she could ensure that The Rock would go on to beat Stephanie’s husband, Triple H, for the WWE Championship. Linda would also go on to slap Stephanie back into place the next night on Raw.

9. DX Crap All Over Shane, Vince, and the Spirit Squad

Ever have one of those days when you feel like the world is just dumping on you?

If you’re Vince and Shane, you know what that feels like, literally! The McMahons and their goons, The Spirit Squad, were the targets of the reformed D-Generation X' s outlandish behavior during their feud. DX goaded the group out by mocking them with impersonations in front of the live audience, which lead to the McMahons and Co. trying to storm the ring. This proved to be an awful idea, as the result was a trap that saw the McMahons get tons of crap dumped all over them.

Though years go by, you’d imagine that Vince and Shane would still have a hard time trying to wash off that stink of embarrassment!

8. Trump Shaves Vince’s Head

Donald Trump might now be turning heads with his shock run for presidency of the United States of America, but, before that, he was shaving heads at WrestleMania.

A long-time friend of Vince McMahon, Donald Trump would be seen every now and then on television at live WWE events. However, a game of one-upmanship between the two seemingly friendly rivals would take Trump out of the stands, and into the ring.

When Vince’s irritation reached a boiling point, he decided to, in typical rich guy fashion, challenge Trump to a wager. The wager would see each man choose a wrestler to fight on his behalf and that the loser would get their head shaved. The intrigue of potentially seeing ‘The Donald’ lose his famed golden hair would add a bit of excitement to WrestleMania 23.

Ultimately, it was Vince’s Umaga who lost to Trump’s Bobby Lashley which lead to the now famous scene of Vince McMahon whimpering as Trump, Lashley, and Stone Cold shaved his head in the middle of the ring at ‘The Granddaddy of Them All’. So distraught was Vince by his new look, that he would go on to sport a Fedora for quite a length of time afterwards.

7. Vickie Gives Steph Some Chocolate

Bosses can get overbearing. In fact, they can get downright mean. This was the case with the working relationship between Stephanie McMahon and her employee, Vickie Guerrero.

Despite her best efforts, Vickie was, for weeks at a time, being berated and harassed by her boss for having done an “unsatisfactory job”. This led to Vickie constantly begging her boss for a stay of execution. She was finally given that opportunity when she was told by the boss that she could remain if she were to beat the McMahon in a match. The whole thing was rigged and Stephanie’s henchwomen tossed Vickie into a pool of pudding.

Stephanie did not stop at this, as she continued to berate Vickie while she was down and out in the pool. Seeing nothing to lose, Vickie made her final act in WWE a memorable one as she grabbed Stephanie and dumped her into the chocolate-y goo, leaving her boss mortified.

6. Vince Pees Himself

Vince’s attack in the hospital at the hands of Steve Austin had him seeing red. This only escalated a raging feud between the two. The attack, as Vince saw it, was the last straw for him. Fed up, McMahon saw it fit that ‘Stone Cold’ be fired once and for all. However, Steve Austin is not someone you simply fire and goes away. No, no, no!

Figuring he had “nothing to lose,” Austin showed up to Raw claiming his was armed and that he was going to finish off Vince McMahon for good. This would lead to an eventual in-ring confrontation at the end of the night, at which point, Austin would get McMahon out of his wheelchair, and onto his knees. ‘Stone Cold’ made Vince McMahon beg and cry, at gun-point, in front of the whole world, to spare his life.

Austin finally decided that he didn’t want to hear anymore and pulled the trigger… to reveal a ‘BANG’ gag. While Austin was having a laugh, a terrified McMahon was left humiliated for all to see, with soaking wet pants!

5. Triple H Marries and Dumps Stephanie

Triple H and Stephanie’s relationship definitely had a weird few years at the beginning.

It began when The Game revealed he drugged the young Ms. McMahon and got married to her at a drive-in chapel, on the night of her televised wedding to Test no less! Then they actually began to like each other and became a pair that would torment WWE’s roster as they ruled supreme at the top. Then, somewhere after all that, Stephanie lied about a pregnancy and tried to get Triple H to renew their wedding vows, which lead famously to Hunter’s dumping her at the alter by calling her “a no-good, lying b****.”

Those are two wedding moments that were truly embarrassing.

4. Vince Gets Attacked In The Hospital

Being cooped-up in a hospital bed is never fun. If you’re Vince McMahon, it’s especially awful.

While trying to heal up and get better, the head of the McMahon family was seemingly never given a moment of peace. Whether it was interruptions from his right-hand henchmen, or a hilarious Mankind invading his space with Mr. Sock-O and balloon animals, Mr.McMahon simply just could not get some quiet.

Just when he thought he did, however, he was confronted by a surgeon, whom then revealed himself to be non-other than, hated foe, the Texas Rattlesnake, ‘Stone Cold’ Steve Austin. Austin proceeded to lay a spectacular hospital-themed beating to his boss, using everything from his IV cord to the bedpan. It would be a moment that, to Vince’s displeasure, no one would ever forget.

3. Stephanie Gets Stinkfaced

The now iconic ‘Stinkface’ finisher has been used by Rikishi to humiliate many men. Like, a lot. However, the humiliation was probably none greater than when Rikishi was finally able to get the young, obnoxious McMahon into the corner for the classic butt-rub after she had cost him his match against then heavyweight champion Stone Cold Steve Austin, who was in cahoots with Stephanie’s ‘Alliance’ group at the time. It made for a classic moment of embarrassment for the McMahon that many fans will not soon forget.

2. Vince and Shane Get Doused

Here’s the thing about getting blasted with beer in front of 20,000 people while you’re hard at work showing off your top new employee: you either like it or you don’t.

In the case of Vince McMahon, and his snotty son, Shane, it’s probably safe to say they didn’t.

While ‘The Corporation’ leader Vince McMahon was trying to triumphantly brag about his new titleholder and “face of the company,” The Rock, Steve Austin came out to make his intentions known: that he was coming for the WWE Championship. And, boy, did he arrive in style!

Coming out in a Budweiser 18-wheeler, Austin seemed to be prepared to end all of The Rock’s weeks-long chirping. He did so emphatically by interrupting the champion’s insult-laden monologue by grabbing a hose from the massive truck and spraying the boss, his son and his prized champion with a blast of ice-cold beer!

While the wild Albany crowd exploded with enthusiasm at the sight of the grown men slipping, sliding, and “swimming” all over the ring, it’s probably a moment that Vince and Shane would like to forget.

1. Vince McMahon’s “Death”

This one could have been huge! It was a massive angle that could’ve been a memorable one for a long time to come. It was ambitious, without a doubt. Vince McMahon’s character was killed in an incredibly suspicious car explosion. It was set up to be an exhilarating murder-mystery for viewers to try to unravel week after week with great anticipation! So, what happened?

Very shortly after the angle was put into motion, the Benoit murder shocked the world. It forced a massive break in ‘kayfabe’ for Vince, who had to appear on television to address the fans, and, shortly thereafter, the media’s scrutiny. The entire ordeal forced McMahon’s hand into altering the landscape of the WWE, the effects of which are still strongly felt today.

Suffice it to say, the whole thing was a colossal embarrassment for Vince McMahon both personally and professionally.

Sources: wwe.com, bleacherreport.com