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  • 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:
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 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)

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  • Paul Lynde's response to the question "In what state was Abraham Lincoln born?"
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 Paul Lynde: In what state? Like all of us, naked and screaming."

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  • 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:
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 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)

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  • 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:
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 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!

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  • 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:
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 Peter Marshall: What is it, now, that Underdog always says?

Wally Cox: Where are my residuals?

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