10 Funniest Vince McMahon Moments in WWE History

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The Mr. McMahon character could very well be the best idea that real-life World Wrestling Entertainment boss Vince McMahon ever came up with during his time with the company. The WWE, then the World Wrestling Federation, was losing the so-called Monday Night Wars to rival organization World Championship Wrestling when McMahon took a page when an actual disagreement he had with wrestler Bret Hart and created the on-air persona who became the most-hated individual in the company and also the best heel in the wrestling business. McMahon changed the face of North American pro wrestling with that character, and the WWE is now alone atop the industry.

Part of what made the character so successful and so profitable was that McMahon was not at all afraid of making himself look silly or downright dumb during a variety of storylines. Many of those angles involved “Stone Cold” Steve Austin, who became the top babyface in the WWE and also the biggest draw in North American pro wrestling in part because of his memorable feuds with McMahon and with McMahon's stables. As great as Austin was during that portion of his career – and he was tremendous – the possibility exists that he would not have been the superstar that he was without the McMahon character being there to play Austin's rival.

Along with Austin, McMahon has feuded with several other wrestlers during the years that he was an active on-air character. This includes the likes of D-Generation-X members and current top babyface John Cena. McMahon has often been on the receiving end of jokes and of pranks during those feuds, and some of those moments have lived on as memorable skits and instances that are replayed on editions of Raw and SmackDown and also via the WWE Network. Say whatever you will about the type of life that he has lived. Nobody can question McMahon's dedication to his company.

10. Trump Shaves McMahon's Head

What was billed as “The Battle of the Billionaires” involving McMahon and Donald Trump was more disappointing than it was a memorable storyline, but its ending did produce a funny moment that occurred at WrestleMania. Following the match in which McMahon's representative Umaga lost, the WWE Chairman was forced to have his head shaved in the middle of the ring. McMahon, who plays the distressed heel as well as anybody in the business, cried out during the shaving as if he was being punished, and he was left completely bald when all was said and done.

9. Mankind in the Hospital

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McMahon had been hospitalized in storyline when he received two unwanted visitors: Mankind and also a clown. Mankind, attempting to endear himself to the boss, brought McMahon candy, while the clown tried to cheer the WWE CEO up with balloons. An angered McMahon did not take kindly to any of these gestures, ultimately throwing both Mankind and the clown out of his room. Karma often catches up with heels in the wrestling business, and that would prove to be the case for McMahon in this instance. Enter Steve Austin and the No. 8 moment that is featured in this piece.

8. Austin Attacks McMahon in the Hospital

We have all been there at one moment or another. Our boss is helpless inside of a hospital bed, and thus we have the urge to beat the crap out of him after pretending to be a doctor in order to sneak into the room. McMahon sold for Austin like a champ in this segment, screaming in pain and then taking a bedpan shot to the head before he was “zapped” by “Stone Cold.” Last but certainly not least was Austin helping McMahon out by inserting an IV in a manner that has to be witnessed to be truly appreciated. Every heel manager in the business should watch segments such as these to learn how to sell when putting a babyface over.

7. Austin “Shoots” McMahon

McMahon found himself prone and in a wheelchair when Austin, who had been fired by the CEO, made his way to Raw to kidnap the man who was his former boss. Austin pushed McMahon to the ring before cutting a promo that included Austin threatening to shoot – yes, shoot – McMahon in front of the in-house crowd and the television audience. McMahon was the perfect terrified heel in this segment, loudly sobbing as he begged off Austin and even “wetting” himself. The cherry on top of this sundae was, of course, McMahon taking a stunner from Austin.

6. THAT Stunner

McMahon was not yet playing the role of the heel authority figure when he was interviewing an agitated “Stone Cold” inside of the ring during an edition of Raw. Austin informed the WWE Chairman in so many words that working “within the system” was not something that interested the wrestler, and he ended his promo by hitting the “Stunner” that is widely regarded as the move that officially kicked off this famous feud. The humor in the moment was McMahon's selling, which involved the boss twitching as he stared off into the distance. McMahon sold death on that night, and it was glorious to behold.

5. Childhood Photos

Vince and Shane McMahon were feuding with D-Generation-X – Shawn Michaels and Triple H – when the McMahons welcomed a new edition to the family: Vince's granddaughter. Not to waste the moment, the DX members showed off what they claimed to be childhood pictures of Vince and Shane during a segment that aired on Raw. The DX duo then finished things off by displaying a picture of the new baby, a youngster who looked rather familiar. This may not have been the most inspired feud McMahon has ever been involved in, but it did bring WWE fans a few funny moments such as this one.

4. The Corvette

McMahon and the WWE have had no problem spending money on destroying property over the years, and that was the case when Steve Austin drove a cement truck up to a Corvette that was, in storyline, owned by McMahon. Stuck in his office and unable to do anything, McMahon could only stare in horror as he watched Austin destroy the vehicle as only “Stone Cold” could. McMahon's facial expressions as he is seemingly as distraught as he has ever before been helped push the segment over the top. You can be sure that the CEO still has plenty of nice vehicles in his arsenal.

3. Pants on the Ground

The Rock has been an ally and also an enemy of Mr. McMahon over the years, and he was playing a babyface when he found himself inside of the ring while his real-life boss had his pants down around his ankles. Rock would not allow McMahon to readjust his wardrobe during the segment, and the “People's Champ” even made the boss walk with his pants on the mat. The skit ended with McMahon taking a Rock Bottom because it just had to, and the crowd erupted in delight at watching the CEO of the company take the finishing move in the center of the ring.

2. McMahon Re-Entrance

The storyline at the time was that McMahon was going to negotiate a potential deal with CM Punk during an on-air segment of Raw as part of the WWE's version of the “Summer of Punk” gimmick.. McMahon was set to make his way to the ring when he did not, upon appearing from behind the curtain, get what he deemed to be an acceptable response from the ring. Always the showman who is capable of thinking on his feet, McMahon refused to make the journey down the ramp and to the ring until the crowd acknowledged him to his liking. While it was not a planned moment, it still remains one of McMahon's best as a character.

1. The Beer Bath

It is quite possible that one of the first things you think of when you recall the McMahon versus Austin feud is the incident that involved “Stone Cold” dousing McMahon and others with beer via a hose that was connected to a beer truck. While the segment was always going to be a hit with whatever crowd was in attendance at the arena on that night, the gem of the bit is McMahon literally selling for beer. That's right. Mr. McMahon, a businessman who was, at one point, the head man of a company that was worth $1 billion, took bumps for beer inside of a wrestling ring. McMahon is the best.