The "You Fool!!" incident, as mentioned on the main page - Overly-Long Gag doesn't come close to describing it. The longest first thousand-dollar game in the history of Hollywood Squares. YOU FOOL!, indeed.
Jillette was generally crass to contestants. Once, he shouted, "You fool! Of course that's not the right answer! I gave it to you on a silver platter!"
This exchange:
Peter Marshall: Paul, true or false: your teeth are about the same size and shape as a pig's.
Paul Lynde: Look who's talking, beaverface!
(Peter makes a face like a beaver's)
Paul Lynde's response to the question "In what state was Abraham Lincoln born?"
Paul Lynde: In what state? Like all of us, naked and screaming."
John Davidson's response to the question "Traditionally, Japanese brides used to shave what off at the time of their marriage?" The question was already practically begging for less-than-wholesome thoughts in regards to the answer, but Davidson (who was trying to avoid them) accidentally took it even further:
John Davidson: Uh...it must be hair on some part of the body. (audience laughs) But where could it be? On the whole, I would say... (audience erupts into laughter; Davidson joins in the laughing when he realizes what he just said, and throws something at the camera too)
When given the question "What country has the highest ratio of doctors to population?", Buddy Hackett gave a joke answer of "the country with the most Jews!" with the equally joking reasoning that "you have a doctor in every family, it's a cousin, could be an uncle. Couple of specialists." He was then shocked when the contestant agreed with him, and even more shocked when his answer (Israel) turned out to be right!
This question:
Peter Marshall: Any boat enthusiast knows that when a man falls out of your boat and into the water, you should yell "Man overboard!". Now what should you yell when a woman falls overboard?
Paul Lynde: Full speed ahead!
She had plenty of groanworthy Large Ham moments on the show, but Melissa Peterman's "Possessed at the Oscars" bit just about cracked everyone up.
Audience members have a good idea of the answer to this question before Gilbert Gottfried does.
And this one:
Peter Marshall: What is it, now, that Underdog always says?