* In 1998, there's his skit with [[Wrestling/MickFoley 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 [[ThrowItIn never tell him what was coming, so every one of the boss' reactions were genuine.]]
* The legendary reveal of who was the "higher power"
-->'''Vince''': '''[[MemeticMutation IT'S ME AUSTIN]]!'''\\
'''Jim Ross''': [[AudienceSurrogate Aw, son of a bitch]]!\\
'''Jerry Lawler''': [[BigWhat WHAT]]?!\\
'''Vince''': '''[[EvilIsHammy IT'S ME AUSTIN!]] [[ChewingTheScenery IT WAS ME ALL ALONG AUSTIN]]!!!'''
* His 2001 skits with [[Wrestling/StoneColdSteveAustin "Stone Cold" Steve Austin]] and Wrestling/KurtAngle during the controversial [=InVasion=] arc.
* [[http://www.youtube.com/watch?v=5JsJh3_-6mM Mr. [=McMahon=] wakes from his coma.]]
* "'CAUSE YOU DESERVE TO BE SCREWED! ''YOU DESERVE TO BE SCREWED!''"
* Tearing his quad at the 2005 RoyalRumble. 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 before being helped out.
** [[BlackComedy 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 PrettyFlyForAWhiteGuy tendencies, turing up his LargeHam and ChewingTheScenery UpToEleven. [[https://www.youtube.com/watch?v=638WkwiaOoY He even challenged the winner between]] Wrestling/JohnCena and Wrestling/ShawnMichaels to a match for "his" title.
-->'''Cena''' (to Shawn): He's lost it.
* June 6, 2011: On ''Raw'', Vince '''finally''' put Wrestling/MichaelCole 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 Creator/DonaldTrump 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 [[http://www.youtube.com/watch?v=Mnkl_rMAhew Hornswoggle, the Great Khali, and Vickie Guererro]] [[AccidentalInnuendo 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.
** Which borders on [[SelfDeprecation Take That Me]], since he really couldn't do BitingTheHandHumor, as he IS the hand.
* Before a match with Wrestling/ShawnMichaels 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'' [[http://www.youtube.com/watch?v=AbsRtuoIDSc 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 [[http://imgur.com/GZUKvFD 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 LargeHam he can be. Look no further than his infamous nWo promo.
* [[http://www.youtube.com/watch?v=N_4eGC2VkBc This moment,]] during which [=McMahon=] does his infamous strut to the ring, absolutely livid...and he nearly breaks both his legs upon entering the ring, deciding to continue angrily staring at everyone while sitting, legs stretched forward.
* [=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 [[http://www.youtube.com/watch?v=0YVUSrNylZI 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.
* [[https://www.youtube.com/watch?v=H7uLr3Hk6F8 This.]]
* 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 Music/RickAstley 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 [[TemptingFate calling the Undertaker and Kane "putrid pussies"]] on September 5, 1998 is distinctly hilarious.
* The very first time he took a Stunner from StoneColdSteveAustin at Madison Square Garden. Most people tend to go [[DwayneJohnson above]] and [[KurtAngle beyond]] the call of duty in theatrically selling the stunner. Vince? He did some sort of "[[BadBadActing 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 RealLife 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 RealLife 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.