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- Let's start with one of Vince's most well-known Crowning Moments of Funny: He was lying the hospital with a broken leg, and Mankind went to try to cheer him up. Vince kicked him out after Mr Socko tried to kiss the leg better. Cut back later, and the nurse asks the doctor if she should help. A very familiar voice replies "Nah, I got it from here." as Vince's face turns to pure horror. Two seconds later, we see Stone Cold Steve Austin beating the hell out of McMahon, then bangs on his leg cast before he smacks Vince around the head with a bedpan, bends him over the hospital bed, grabs an enema tube and shoves it up Vince's ass. The last bit might have been fake but it's still a CMoF.
- Umaga versus Bobby Lashley where Vince put his hair on the line against Donald Trump's at Wrestlemania 23...with Stone Cold as the referee. Umaga lost, and Vince was subjected to Trump, Lashley and Stone Cold shaving him bald.