- 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. 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.
- After the X-player falls for Gilbert's bluff about Nellie Bly rowing the Atlantic Ocean in 72 days (the correct answer was going around the world), Tom says "If you're just tuning in, welcome to the Gilbert Gottfried Show."
- Going to commercial, Bergeron says "We'll be right back with more of the Gilbert Gottfried Hour!" When the break is over, Bergeron seriously states "Welcome back to Biography's tribute to Gilbert Gottfried."
- The final question to the round. The X-player agrees with Gilbert's answer that "smog" is a combination of the words smoke and fog. Cue Tom rising from his podium, exclaiming "SMOKE AND FOG!'" with an expression on his face that just SCREAMS "Hallelujah!" Just before he asks said question, Tom says "By the way, if we run out of time during or any other game, we're all going out for drinks."
- 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. Even better, Gilbert and the audience member are both wrong.
- And this one:
Peter Marshall: What is it, now, that Underdog always says?
- At one point, when Rosie O'Donnell was one of the panelists, she asked Tom if they could swap places for a few questions, and he said "Sure, Why Not?".
- 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?
- When Tom Bergeron was host, he'd express frustration at explaining the rules every episode (especially when the contestants admitted they couldn't play tic tac toe)- one Whoopi episode had him going "It's tic tac toe, for god's sake!", and it came to the breaking point during the final week of H2, where crew members played and he commented he no longer had to be nice to the contestants, and he then ranted "Some of those people didn't even know how to play Tic-Tac-Toe!"
- Meta example, but a mid-70s Rich Little special had this parody mashup of this and The Towering Inferno, The Towering Squares, featuring much of the regulars (including Paul Lynde) on the actual set who are trying to flee the smoking Squares, and yet Peter Marshall continues with the game as if nothing's wrong.
Narrator: The Towering Squares! Where else could you see first-degree stars receive second-degree burns?!
- And at the tail end, the narrator informs us that playing on the same bill is Let's Make an Earthquake, where you can see "Monty Hall crumble before your very eyes".
- One episode during Tom Bergeron's run had him revealing the answer to a question before the contestant could say whether she agreed or disagreed with the celebrity's answer. Whoopi Goldberg quipped (paraphrased) "I think I hear the producers calling up John Davidson now!"
- From the H2 days, this contestant's enthusiastic responses to winning a car and $25,000, respectively; in fact, "enthusiastic" might be too strong a word....
- This episode from the Whoopi era has a carload of them, chiefly a Call Back to the "You Fool" incident thanks to another block-and-win situation with Gilbert (with Tom noting this time it was "mercifully short compared to the last time this happened"), but also Whoopi trying to claim disability from one of the contestants, then claiming the phrase "strike while the iron is hot" was invented by "the maid's union", and later on saying in response to a question she was going to avoid any penis or Viagra jokes. Which was promptly followed up by a dose of Hypocritical Humor, as she then jokes in response to a zinger from Coolio about the "charity stripe" in basketball being tatooed across Dennis Rodman's ass that the stripes are skidmarks, followed by Tom pointing out "This from the woman who wouldn't do a Viagra joke."