- 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 The Hollywood Squares. YOU FOOL!, indeed.
- Jillette was generally crass to contestants. In the same episode he shouted, "You fool! You fool! Of course that's not the right answer! I gave it to you on a silver platter! Look at me! I lied!"
- "Gilbert Gottfried for the win!" Truer words were never spoken.
- 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.
- This gem:
Peter Marshall: Paul, what did ancient Romans traditionally bake into every loaf of bread they made?
Paul Lynde: A Christian!
(the correct answer was a coin)
- 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:
- 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 "We 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.
- Later on, Penn Jillette gives his answer to a question. The contestant disagrees. Penn was correct... so he says "YOU FOOL!"
- 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?
- During one week, "Macho Man" Randy Savage joked about how the bottom row of squares that week were the most-awesome. Who were the ones in the bottom row that week? Himself, Rip Taylor and Bear in the Big Blue House.
- Randy Savage's interactions with Bear were often hilarious, such as performing a fist-bump with him.
- Another hilarious Gilbert Gottfried moment:
Tom Bergeron: What should you do about a hairy back?
Gilbert Gottfried: I usually close my eyes and imagine she's wearing an alpaca sweater.
- Another question:
Peter Marshall: True or false: At a recent hearing, opponents of fluoridated water argued that too much fluorine in a person's system could cause an uncontrollable desire for sex?
Paul Lynde: (excitedly) HEY, CULLIGAN MAN!
- Even before they were merged into a single hour-long programme, the series had a (mostly) friendly rivalry with Match Game, which was the subject of several zingers:
Peter Marshall: What early television show featured characters named Fletcher Rabbit, Beulah, Madame Oglepuss, and Colonel Crackie?
Paul Lynde: Aren't they still regulars on Match Game?note
Peter Marshall: Paul, what would happen if you sank in quicksand?
Paul Lynde: You'd replace me with Charles Nelson Reilly.
- From the NBC finalenote :
Madame: Peter, I'm sorry you're leaving and not going to be on in the morning. I tried everything I could... I even fucked Silvermannote . It's true, it's true!
Peter: Maybe that's what did it!
Madame: It just goes to prove that you can fuck all of the people some of the time and some of the people all of the time, but you can't fuck with the people all of the time!
- Even on Hollywood Squares, Rodney Dangerfield gets no respect...
Peter: According to genetic experts, do scientists think they'll really ever be able to slow down the effects of aging.
Rodney: Definitely. Let me tell you about this now. Aging, I mean, I'm getting old myself...
Miss Circle: Yes, I agree.note
- A slip-up from the seemingly innocent Florence Henderson:
Peter Marshall: Will humming help your tennis game?