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  • His over-the-top performance of "Stand Back" at the 1987 Slammy Awards. D-Generation X and Chris Benoit and Chris Jericho had field days with reminding Vince McMahon of this Old Shame.
  • His commentary with Jesse Ventura, which made WWF Superstars of Wrestling a must-see program between 1986-1990. Examples abound:
    • Ventura questions McMahon whether Juan Valdez note  was the same man as the mascot for the Juan Valdez line of gourmet coffee. "IT'S NOT THAT JUAN VALDEZ!!!!!" snaps McMahon.
    • Vince relentlessly making fun of jobber Steve Reese (during a squash match against Bad News Brown), at one point calling him a parakeet stripped of all his feathers. Ventura responded in kind by making fun of McMahon's physique.
    • In a match from Madison Square Garden pitting Koko B. Ware vs. Frenchy Martin, that re-aired on Prime Time Wrestling, McMahon and Ventura both talk about parrot soup and what ingredients would be needed to make a delicious soup. This, after Ventura talks about Martin winning the match and wondering if he'll claim Frankie (Ware's parrot) afterward.
  • In 1998, there's his skit with Mankind while Vince was recovering from his ankle injury. Which introduced the world to "Mr. Socko".
  • On the same day as the debut of Socko, Vince McMahon was beaten up by "Stone Cold" Steve Austin in the hospital. The attack included Vince getting brained by a bedpan, shocked by a defibrilator, and given a forced enema with an IV drip.
  • The legendary reveal of who was the "higher power"
    Vince: IT'S ME, AUSTIN!
    Jim Ross: Aw, son of a bitch!
    Jerry Lawler: WHAT?!
    Vince: IT'S ME, AUSTIN! IT WAS ME ALL ALONG, AUSTIN!!!
    • This is followed by Linda announcing she's just made Austin CEO of the company. Vince's look of abject horror is a thing of beauty.
  • His 2001 skits with "Stone Cold" Steve Austin and Kurt Angle during the controversial InVasion arc.
  • Mr. McMahon wakes from his coma.
  • "'CAUSE YOU DESERVE TO BE SCREWED! YOU DESERVE TO BE SCREWED!"
  • In the videos leading up to Diamond Dallas Page's debut, when he was stalking the Undertaker's wife Sara, that's not DDP's voice talking about her. Vince voiced those over himself with distortion added. And before you ask, yes, there is a clean version, and it's either hysterical or REALLY REALLY creepy.
  • This moment, when he tore his quad at the 2005 Royal Rumble. He ran to the ring to restart the match after Batista and John Cena caused a double-elimination at the end, not wanting 1994 to happen again. He ended up doing the spot sitting in the ring, legs stretched out, before being helped out. Slightly less funny: he refused medical attention and walked back on his own, causing a tear to his other quad.
  • The July 3, 2006 episode of Raw when D-Generation X "hijacked" the production truck subjects him into various practical jokes like having his use of public restroom broadcasted, and screwing with him during his promo like tampering his microphone and other shenanigans.
    "*High pitched voice* Dammit you people think this is funny!"
    "*Low pitched voice* Sounds like Darth Vader... Damn it, you'd better normalize my mic!!"
  • During his run as ECW Champion, he actually took on some Pretty Fly for a White Guy tendencies, turing up his Large Ham and Chewing the Scenery up to eleven. He even challenged the winner between John Cena and Shawn Michaels to a match for "his" title.
    Cena (to Shawn): He's lost it.
  • June 6, 2011: On Raw, Vince finally put Michael Cole in his place.
    Cole: May I have your attention please... I have just received an email from the anonymous Raw general manager.
    Vince: MICHAEL COLE, SHUT UP!
  • Needless to say, all of us enjoyed seeing Vince give Donald Trump a taste of his own medicine.
    About the only thing I can say to ya here tonight is... DONALD TRUMP, YOOOUUUUUUU'RE. FIRED!
  • The moment when Hornswoggle is revealed as his son. As HHH howls with laughter, Vince just stands there with a look of a man clearly wishing he could be struck dead at this very instant.
    • And that's before Hornswoggle clutches his leg for a hug.
    Jerry Lawler: I think Mr. McMahon has just lost the will to live.
  • December 10, 2012: Mr. McMahon catches Hornswoggle, the Great Khali, and Vickie Guererro in a rather awkward position. He gives them a shocked look before the next thing he says takes the cake:
    I thought this was supposed to be a family show.
  • Before a match with Shawn Michaels Vince decided to lead his family in a prayer. It opened with Vince saying, "God, you don't like me, and I don't like you!"
  • Have you heard Vince McMahon's commentating for Gary Strydom in the World Bodybuilding Federation?
    • Have you seen the mash-up of this footage with the time Stacy Keibler 'auditioned' to be his secretary, resulting in this?
  • Really, any of his "angry" promos can fall under this. Depending on your sense of humor, it's either unintentionally funny…or unintentionally HILARIOUS seeing just how much of a Large Ham he can be. Look no further than his infamous nWo promo.
  • McMahon's Kiss My Ass club debut is very funny (considered that Vince's a face at this moment). Regal's expression during the whole skit and King Lawler's uncontrollable laugh really made the Promo. The fact that Vince bended his ass to Regal when he kissed it just made the whole thing even funnier.
    • The "Kiss My Ass Club" angle ended with Vince getting an unfortunate taste of his own medicine. Due to circumstances, Vince McMahon was set up so he would have to kiss someone's ass. The Rock first says he's not going to kiss his ass, and calls out Jim Ross. The Rock stops Vince from kissing JR's ass, and calls out Trish Stratus. Vince eagerly moves to kiss her ass, but is stopped again by The Rock. Finally, The Rock brings out the real ass Vince is going to kiss: Rikishi. This ultimately ends with Vince getting Rock Bottomed and having his face shoved into Rikishi's ass.
  • Just watch any of HSQ moment against Vince's favorite heel. He will make funny faces out of surprise that just as memetic as Cornette face had they given a chance.
  • Mr. McMahon Dances with the Funkadactyls. What sells it even more is after the dance segment, he runs into Zack Ryder, who looks like he just witnessed a murder. The two stare at each other, and then McMahon gives Ryder a "Woo woo woo, you know it!", and walks off.
  • Undoubtedly the highlight of his infamous Million Dollar Mania giveaway was the moment he called his first lucky recipient, only to find that the guy had a Rick Astley ringback tone. And so it came to pass that on June 10, 2008, Mr. McMahon got Rickrolled on live television.
  • Watching McMahon run for his life right after calling the Undertaker and Kane "putrid pussies" on September 5, 1998 is distinctly hilarious.
  • The very first time he took a Stunner from "Stone Cold" Steve Austin at Madison Square Garden. Most people tend to go above and beyond the call of duty in theatrically selling the stunner. Vince? He did some sort of "flop-around-like-a-dead-fish" sort of thing. He just kind of slides awkwardly over the top of Austin’s body and spreads eagle once he hits the canvas looking face into the lights more dumbstruck by what just happened than injured.
    • As Chris Jericho puts it, it's a terrible sell of the move, but who's telling that to Vince?
  • A Real Life example: In Bret Hart's book, he talks about the time he went with several guys and got drunk. Not such a big deal, but then Vince takes the guys to Ric Flair's hotel room (Flair was still in WCW at this time), demands Flair's room key and then along with the guys, they proceed to completely trash Flair's suite. It's a hilarious story.
  • Another Real Life example are his various and hilarious quirks. Punctuating every sentence by calling someone "pal", his hatred of sneezing, his love of ketchup steak, not realizing whether or not certain talents are still employed... Vince is one quirky and fascinating guy. The stories you hear about these various quirks are often hilarious.
    • There are also many, MANY stories of Vince pulling stunts that are just as goofy/insane as anyone else in the WWE. For instance, here's BROKEN Matt Hardy telling about Vince trying (and failing) to beat Kurt Angle in a wrestling match.
    • As a case of him forgetting, one time, Vince asked the ECW team to come up with something involving Tommy Dreamer, because he draws in ECW in early 2010's or so. However, by then, Tommy had quietly left, and everyone knew that, except for Vince. When he was told Tommy was gone, Vince just thought he died for a minute and downright refused to believe he was not working for them. Everyone just played along and brought back Tommy.
    • He did not know what a burrito was for the longest time, which is damning because he was said to be eating a steak burrito for years. Man just didn't question what he was eating.
  • "SHUT UP, I'M TALKIN'!!!!"
  • After Mick Foley won his first WWE Championship, Vince had a little Villainous Breakdown:
    Vince: "Oh no, no, not Mankind!" (Paraphrased from the original)
  • In 2005, Eric Bischoff is about to strip John Cena of the WWE Title and give it to Kurt Angle. Vince shows up to put a stop to this. When Bischoff whines about Cena attacking him, Vince does a beautiful job mocking him, pursing his lips and moaning.
    Vince: He, he put his hands on me..Buh-buh-buh...He...he attacked me...He buh-buh-buh, he shut the hell up!
  • Oh, and his strut is just legendary.
  • The night after WrestleMania 33, he came out to a riotous ovation...capped off with the crowd singing his entrance theme. And it's clear Vince has no clue how to react to this.
  • This moment, when Vince told this in a promo to Shawn Michaels before Shawn and HHH had to face him and Shane in a tag team match:
    Vince: "You and God vs me, Vincent Kennedy McMahon and the product of my semen, MY SON SHANE!!!"
    (Shane's face slowly turns towards Vince as if he's about to say "What the fuck, dad?", while Shawn is struggling to contain his laugh)
  • The opening segment of WWE SmackDown 1000. How does Vince solve his children's inter-brand bantering in the middle of Truth TV? He would entertain everyone with one simple solution: A DANCE BREAK!
  • A story recounted by Curt Hawkins, Vince McMahon held a conference with all the wrestlers discussing about changes and the future of the business, this was around early to 2010. At one point, one Michael Tarver (former member of the Nexus) spoke up about how the changes will affect their pay, and Vince says, "Excellent question, Shelton", and the room erupted in laughter, all the while Vince couldn't figure out why.

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