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[[folder:Peter Marshall (1966-81)]]
* This exchange:
-->'''Peter Marshall:''' Paul, true or false: your teeth are about the same size and shape as a pig's.\\
'''Creator/PaulLynde:''' 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?"[[note]] The actual answer was eyebrows [[/note]] The question was already practically begging for less-than-wholesome thoughts in regards to the answer, but Davidson (who was trying to ''avoid'' them) [[AccidentalInnuendo accidentally]] took it even further:
-->'''John Davidson:''' Uh...[[CaptainObvious it must be hair on some part of the body]]. ''(audience laughs)'' Wonder where could it be? [[ThatCameOutWrong On the whole]], I would say... ''(audience erupts into laughter; Davidson joins in the laughing when he realizes [[DoubleEntendre what he just said]], and he throws a cushion at the camera, too)''
* When given the question "What country has the highest ratio of doctors to population?", Creator/BuddyHackett gave a joke answer of [[https://www.youtube.com/watch?v=ZcTu0-1rqAU "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, [[AccidentallyCorrectWriting and even more shocked when his answer (Israel) turned out to be right!]] (He had thought the correct answer was Sweden.) [[https://www.youtube.com/watch?v=2au4EHncAxU Here's the uncut version in all its glory.]]
* 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!
* And this one:
-->'''Peter Marshall:''' What is it, now, that WesternAnimation/{{Underdog}} always says?
-->'''Wally Cox:''' [[ActorAllusion Where are my residuals?]]
* 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 ''Series/MatchGame'', 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]] The correct answer is ''[[http://en.wikipedia.org/wiki/Kukla,_Fran_and_Ollie Kukla, Fran, and Ollie]]''.[[/note]]\\
\\
'''Peter Marshall:''' Paul, what would happen if you sank in quicksand?\\
'''Paul Lynde:''' You'd replace me with [[Series/MatchGame Charles Nelson Reilly]].
* From the NBC finale[[note]](Obviously edited later, here is what was really said, albeit paraphrased.)[[/note]]:
-->'''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 (dated) Silverman[[note]](Fred Silverman, then president of NBC.)[[/note]]. It's true, it's true!\\
'''Peter:''' Maybe that's what did it!\\
'''Madame:''' It just goes to prove that you can fuck (fool) all of the people some of the time and some of the people all of the time, but you can't fuck (fool) with the people all of the time!
** Moments later, when Madame is chosen as a bonus round prize she says about her prize card, "It's from Fred, he says he's sorry."
* Even on Hollywood Squares, Creator/RodneyDangerfield 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]](For the record, Rodney's true answer was "yes", she DID agree, and she got the Square.)[[/note]]
* A slip-up from the seemingly innocent Florence Henderson:
-->'''Peter Marshall:''' Will humming help your tennis game?\\
'''Florence Henderson:''' This struck me funny. Will humming help my tennis game? Sure, why not? [[AccidentalInnuendo It takes your mind off your balls]], or something... ''(audience erupts into laughter; Henderson [[OhCrap realizes]] [[ThatCameOutWrong what she said]] and [[HeadDesk hides her face]])''
* A mid-70s Creator/RichLittle special had this [[https://www.youtube.com/watch?v=f8-nmqm5RlM parody]] [[JustForFun/XMeetsY mashup]] of this and ''Film/TheToweringInferno'', ''The Towering Squares'', featuring much of the regulars (including Paul Lynde) on the actual set who are [[ScrewThisImOuttaHere trying to flee the smoking Squares]], and yet [[TheShowMustGoOn Peter Marshall continues with the game]] [[WeirdnessCensor as if nothing's wrong]].
-->'''Narrator:''' The Towering Squares! Where else could you see first-rate stars receive second-degree burns?!
** And at the tail end, the narrator informs us that playing on the same bill is ''[[Series/LetsMakeADeal Let's Make an Earthquake]]'', where you can see "Creator/MontyHall crumble before your very eyes".
* This one involving [[Series/SesameStreet Oscar the Grouch]]:
-->'''Peter Marshall:''' Oscar, true or false, birds really like to watch other birds make love.\\
'''Oscar:''' Hey, listen, I'm from a kids show!\\
'''Peter:''' Well, I think you know Big Bird, don't you?\\
'''Oscar:''' Yeah, but he's only six years old! He doesn't know anything!
* When Lynde gets asked about food preparation:
-->'''Peter Marshall:''' According to the food editor of the ''Dallas Morning News'', what's the best reason for pounding meat?\\
'''Lynde:''' Oh, loneliness.
* This exchange from a question:
-->'''Peter Marshall:''' What does a person from Philadelphia dunk his pretzel in?\\
'''Marty Allen:''' A girl from New Jersey!
* In general, whenever a celebrity makes announcer Kenny Williams crack up during the intro.
[[/folder]]

[[folder:John Davidson (1986-89)]]
* The 1986 premiere had center square Creator/BronsonPinchot fielding a question regarding what the White House telephone operator says to you if you try to call and ask for (then-) President Reagan. To reveal the answer, John has Bronson dial the White House from a (working) telephone installed in his square, with Bronson asking for the President in his [[Series/PerfectStrangers Balki]] voice. [[TakeAThirdOption The operator promptly hangs up on him.]]
* This exchange:
-->'''John:''' You're watching balls go back and forth at speeds of up to 160 miles an hour, in what sport?\\
'''Joan Rivers:''' Oh, John. Jogging.
* Another moment from the Davidson era:
-->'''John:''' You heat some raw milk to 143 degrees, and you keep it there for about a half an hour. What have you just done?\\
'''Jm J. Bullock:''' Well, for one thing, I've scorched the hell out of my cow!\\
(several seconds later, as Jm tries to keep it together and everyone else is laughing)\\
'''Jm J. Bullock:''' Welcome to game show hell, everybody!
[[/folder]]

[[folder:Tom Bergeron (1998-2004)]]
* The "YouFool" incident, as mentioned on the main page - OverlyLongGag doesn't come ''close'' to describing it. The longest first thousand-dollar game in the history of ''Hollywood Squares'', the out-of-time sound effect played right after the last square was won, resulting in there being no Secret Square game (the prize meant to debut that episode debuted alongside the next Secret Square prize the next episode). [[https://www.youtube.com/watch?v=iFMaPUtCi9o YOU FOOL!]] indeed.
** Penn 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!"
** "Creator/GilbertGottfried 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." The joke answer on that question, "Getting through to the cable company!" was also a standout that episode.
** 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 this or any other game, [[INeedAFreakingDrink we're all going out for drinks]]."
** He also tells the losing circle player that she's getting the usual $500 consolation prize and "it's in psychological counseling."
* She had plenty of groanworthy LargeHam moments on the show, but Creator/MelissaPeterman's [[https://www.youtube.com/watch?v=5rK0__tMW2g#t=218s "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 "[[CallBack YOU FOOL!]]"
* Audience members have a good idea of the answer to [[https://www.youtube.com/watch?v=y45nmSyfDno#t=107s this question]] before Gilbert Gottfried does. Even better, Gilbert and the audience member are both wrong.
** The [[https://www.youtube.com/watch?v=GyLzkk5W114 uncensored, unedited footage from that episode]]. Hoo boy.
* 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".
** Same episode, but not during the time they swapped seats,
--->'''Tom Bergeron:''' Which was the first [[Music/TheBeatles Beatle]] to perform in Moscow?
--->'''Rosie O'Donnell:''' (without missing a beat) Volkswagen![[note]]The correct answer was Paul [=McCartney=][[/note]]
* During one week, "Macho Man" Wrestling/RandySavage 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 '''Series/BearInTheBigBlueHouse'''.
** Randy Savage's interactions with Bear were often hilarious, such as performing a fist-bump with him.
** This little moment:
--->'''Tom Bergeron:''' Scientists say its physically impossible to keep your eyes open when you do it. When you do what?
--->'''Bear in the Big Blue House:''' [[TakeThat Watch C-Span.]] Have you seen it? "Mister speaker, the great state of-"ZZZZZ....
* Another hilarious Creator/GilbertGottfried 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.
* Tom would express frustration at explaining the rules every episode (especially when the contestants admitted they couldn't play TabletopGame/TicTacToe) -- 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!''"
* 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 [[MythologyGag John Davidson]] now!"
* [[https://www.youtube.com/watch?v=A9tWVkc8KxM This]] [[https://www.youtube.com/watch?v=TPErQgQdeqY episode]] from the Whoopi era has a carload of them, chiefly a CallBack 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"). It kicks off with Whoopi trying to claim disability from one of the contestants, then claiming the phrase "strike while the iron is hot" was invented by "[[BlackComedy the maid's union]]". Later on, she says in response to a question she was going to avoid any penis or Viagra jokes. Which was promptly followed up by a dose of HypocriticalHumor, as she then jokes in response to a zinger from Coolio about the "charity stripe" in basketball being tattooed across Dennis Rodman's ass that the stripe is a skidmark, followed by Tom pointing out "[[LampshadeHanging This from the woman who wouldn't do a Viagra joke.]]"
* [[https://www.youtube.com/watch?v=rOU9r1DcwGI This little known blooper]], where Tom gets confused over who won the game and gets lambasted by Whoopi over the blunder.
-->'''Bergeron''': I guess that Emmy nomination is shot to shit right now!
* [[https://www.youtube.com/watch?v=WX3VDmB-taA&t=100s One "It Just Ain't Right" episode]] saw Gilbert Gottfried failing ''spectacularly'' to pronounce the "Fraggle" in ''Series/FraggleRock'' [[OverlyLongGag for a good minute]].
* Jake Johannsen making the best of the word "differences" in [[https://www.youtube.com/watch?v=_pZvtrPqbjo&t=605 this]] clip:
-->'''Bergeron:''' The National Enquirer tells us we'll be seeing something different about the actresses on Baywatch. What?\\
'''Johannsen:''' Next season, all the actors and actresses on Baywatch will be sporting the high-resolution plastic nipples from Japan.
* This zinger given by Triumph the Insult Comic Dog on the Bergeron era.
-->'''Tom:''' Who's the only dog ever to make ''People'' magazine's best-dressed list?\\
'''Triumph:''' Uh... Sally Jesse Raphael.
* October 23-29, 2002: Charlie Brown, one of the most enthusiastic contestants the show ever had. In his five-day run (where he won $124,129), he rightfully demonstrated the proper way to celebrate winning a [[https://www.youtube.com/watch?v=xKcwDlDkaGA car]], [[https://www.youtube.com/watch?v=Iv7mNW_3JBs $25,000]], and [[https://www.youtube.com/watch?v=uby0czBMQpQ a trip around the world]]. In fact, "enthusiastic" might be too strong a word....
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