"'CAUSE YOU DESERVE TO BE SCREWED! YOU DESERVE TO BE SCREWED!"
Tearing 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 before being helped out.
Slightly less funny: he refused medical attention and walked back on his own, causing a tear to his other quad.
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.
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 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.
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.