- In 1998, there's his skit with Mankind while Vince was recovering from his ankle injury. Which introduced the world to "Mr. Socko".
- Really, anything between Foley and McMahon. Vince told Foley to never tell him what was coming, so every one of the boss' reactions were genuine.
- The legendary reveal of who was the "higher power"
- 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!"
- 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.
- 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 11. 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!
- Recently on 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.
- 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.
- 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 Rick Rolled 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.
- 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.
- "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)
- 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 Mc Mahon 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)