If you know that Hollywood Squares is a funny show already, then you haven't seen nothing yet. Have a look at some incredibly hilarious bluffs and moments from the show that I have found. Enjoy, and have a good laugh!
The Pink Sweater Incident (October 27, 1998)
The funniest thing happened in this show. On a dare put forth by Whoopi, Tom takes up the offer of wearing Bobcat Goldthwait's pink cardigan for one round (the first one). But it doesn't stop there. Bobcat also strips off his blue jeans right in his square and hands those off to the courageous host, although he puts them on. I swear, that had to be without a doubt, the funniest thing I've ever seen!
Bobcat Asleep at the Switch (September 29, 1998)
Contestant: I think I'll wake up Bobcat.
Tom: Bobcat! (Zoom in on Bobcat, asleep. Crowd cheers as he finally jerks up)
Tom: What is Prince Charles' favorite sport?
Bobcat: Gee, I don't know...Pocket pool...Let's see, uh...Hacky sack. (He shrugs. Crowd laughs)
Contestant: I agree.
Tom: You agree...?
Bobcat: ARE YOU NUTS!?
Tom's Tradeoff (November 4, 1998)
At the end of the first round, Rosie O'Donnell asks Tom if she could host for one round and she also asks how he felt about being a square (although she drops a hint to him in the previous day's show), so the trade was made. Rosie made a very convincing host (she kept calling herself by Tom's name) while Tom sat in Rosie's square flinging Koosh balls while waiting for his turn. Eventually, he got his turn and got his question right although the contestant disagreed with him.
Secret Square Slip-Up
This blunder occured during the first day of taping for the new series on August 1, 1998. Someone forgot to black out the studio monitors before the Secret Square game, so the Secret Square was actually revealed to the audience. When the audience saw it was Brian Austin Green, every female member of the audience went berserk, so right away the first contestant picked him and won the prize for a correct answer. However, the game was restarted with a different star though the contestant got to keep the prize. OOPS!
Sci-Fi and Deadheads (November 10, 1998)
Gilbert: Maybe this isn't the time to forge a complaint, but would someone tell Cindy Crawford that I came here to work, and not to be her own personal sex toy (Laughing). I'm SICK of it! Now what's your question?
Cindy:Which one's Gilbert?
Tom:The bottom row by the way is the Science-Fiction Row. (Audience laughs, Tom starts Gilbert's question) In the world of music, they're called "Deadheads". What are they?
Stephen Baldwin: Finally he says something intelligent!
The Naked Truth (November 10, 1998)
Tom: When Lady Godiva rode naked on a white horse through the town of Coventry, who was the only one that supposedly looked at her? Right.
Stephen: Well, whoever it was I'm sure he wasn't disappointed (Audience laughs)
Gilbert (poking his head into Stephen's square): Can I break for lunch? (Tom laughs)
Gilbert and Golden Balls (November 11, 1998)
Tom: What does a sign with three golden balls indicate, Gilbert?
Gilbert: I don't know but I'm sure it itches like hell
A Lot Of Bull (November 17, 1998)
Tom: What is different about the bullfights in Portugal?
Robert Wuhl: They're held in Greece
Tom's Turn To Slip Up (October 15, 1998. Submitted by Paul Crabbe)
Tom: If you were on the Lewis and Clark expedition and you asked a 16-year-old girl named Sacajawa...
Ben Stein: Sacajawea!
Whoopi: Sacajawa? (Laughing)
Al Roker: Sacajawa? That's a Starbucks Drink!
Bruce's Complaint (From "The Nanny: Making Whoopi", November 18, 1998)
Bruce: All right, that's it. I want a new square. Brad Pitt wouldn't get picked in this box. I wanna be on top of Whoopi.
Whoopi: Honey, if you was Brad Pitt, you would be!
Tom (trying to break it up): All right, all right.
Fight of the Century: Tom vs. All Comers (November 19, 1998)
It was Mr. X's turn to choose a square, so he picks Bruce Vilanch. Tom asked of Bruce what Ray Bolger's character wanted in the movie The Wizard of Oz, and Bruce responded "Ray was the Scarecrow, so he wanted a brain". And what did the contestant do? HE DISAGREED, THAT'S WHAT! Bruce was absolutely right, so Tom got up and proceeded to bean the male contestant with the question card, resulting in massive hysterics by the other stars. Obviously, the male contestant had never seen the movie, prompting Whoopi to explain things by saying "It's 'The Wizard of Oz', man! The house falls on the witch and Dorothy is chased by all those little white people!" And in the aftermath...Circle ended up capturing Bruce's square.
A Stately Pun (From Week 7. Submitted by Alex Anderson)
Tom: What is the state song of Kansas?
Bill Maher: "Yes, We Have No Black People"
G.I. Impaired? (November 17, 1998)
Tom: G.I. Joe is a manly doll for sure. After all, the term "G.I." means that he's a fighting man, but what did "G.I." originally stand for?
Robin Williams: If we're talking about the doll, we're talking about genitally impaired!
Mistaken Laughter (October 1, 1998)
Tom (to Jackée Harry): Who wrote the book "Sex for Dummies"?
(Whoopi's laughing, but Jackée thinks it's Bobcat)
Jackée (to Bobcat): Shut up, Bobcat!
Whoopi: That wasn't Bobcat, that was me, girl!
Holy Smoke! (November 10, 1998)
Caroline Rhea: I think Fred's a little...naughty. Anyway, go on.
Tom: And this appeals to you (Starts the question). Both Bill Clinton and the Pope played this game in their youth. What? (Laughter)
Billy Baldwin: Don't go there!
Caroline: I'm not going to say "Hide the Virgin," okay?
A Different Introduction (November 13, 1998)
Tom: Let's welcome our Gang of 9, hello stars!
Stars: Hello, Tom! (Whoopi does her greeting a la Eartha Kitt. Tom notices this)
Tom: Eartha Kitt's in the Center Square today.
Whoopi: Yes I am today, Tom.
Whoopi: And I'll be answering questions as they are asked of me.
Tom: A little growl maybe?
Whoopi: Growl. (Laughter. Tom is taken aback)
Tom: Let's meet our contestants while I fan myself.
Attack of the Jerry Springer Wannabes (October 16, 1998)
Tom: All right, Al. As reported in Sports Illustrated, college baseball players use these, pros can't, some say they have led to a scoring orgy. What are they?
Al Roker: Uh, bigger balls. (Laughter)
Whoopi: I agree with that! (More laughter)
Al: I'm sticking with that.
Tom: Okay. Bigger...balls. (Laughter)
Debbie/Miss Circle: I'll agree.
Tom: Aluminum bats (Al: Good choice!) X gets the square.
Gilbert Gottfried (interrupting): He just wanted to say "bigger balls!" (More laughter, Tom is in hysterics)
Al: Yes I did.
Gilbert: I know!
Al (yelling at Gilbert): You're just sorry YOU couldn't say it!
Tom (to Mr. X): All right, Dan.
Gilbert (to Tom): Would you ask me that question, so I can say "bigger balls" please? (Laughter)
Whoopi: Yeah, but Gilbert, with you it's wishful thinking! What's going on?
(Gilbert is shot down. Tom's trying to break up the fight, while the crowd cheers Whoopi's comment)
Tom (to Dan): Okay. Before this turns into the "Jerry Springer Squares," why don't you...
The Birth of a New Catchphrase
Tom: Supreme Court justice Stephen Bryer used a certain word that caused quite a stir in the legal world. What was it?
A Conversation with Judge Judy (February 2, 1999)
Tom: Your book title is my favorite title in publishing.
Judge Judy: You wanna say it?
Tom: Don't pee on my leg and tell me it's raining. (Laughter. He goes into the question) Judge Judy, Judge Wapner has a new TV show where he only presides over cases involving what?
Judge Judy: Judge who? (Laughter)
Andrea Thompson: You go, girl!
A Bee-dazzling Thought (January 26, 1999)
Tom: How does a bee become a queen bee?
Little Richard: By going to Ken Starr's house!
Freak-Out (January 26, 1999)
Tom: According to Dr. Joyce Brothers, what is the best way to freak people out on an elevator?
Gilbert Gottfried: Say "Okay everybody, it's time for your prostate exam!" (Tom cracks up)
Tom: If a ballplayer is "up for a cup of coffee", what does it mean?
Gilbert: It means he's taking a shower with Juan Valdez
Oscar Clip (January 26, 1999)
Tom: What is Greenpeace?
Whoopi: What every frog wants, Tom. (Laughing) Every frog wants Greenpeace. (Caroline Rhea is laughing) It's really not easy, and you can just stop laughing, Caroline.
Caroline: I think it's really funny! (Whoopi is near tears)
Whoopi: No, it's really sad. Kermit is out there all the time fighting, fighting for peace, along with the environmentalists...
A Plain and Simple Answer (January 28, 1999)
Tom: If a geisha gets your getas off, what has she done?
Gordon Clapp: Her job!
Armed...and Dangerous (February 15, 1999)
Tom: Where in Wheatridge, Colorado were the recently deceased taxed eighteen dollars?
Kevin James: I actually know this because I started my dance career in Wheatridge. It's an embalming tax
(Leah Remini looks over her shoulder to the right)
Leah: Richard is touching my butt!
(Cut to Richard on all fours, checking out Leah's butt. Tom comes running down the steps with the bottle of Disco Sweat, races across the stage, leans into Richard's square and sprays him in the face)
Tom: Get in your square! (continues spraying) Get in your square! (Returns to the podium. Audience is laughing and applauding wildly)
Kevin: Tom, I feel different
Tom: It's an embalming tax
Kevin: It's an embalming tax
Jim (Mr. X): I disagree
Tom: It's a hotel tax they had to pay while awaiting burial. X gets the square
(Whoopi is in shock)
Whoopi: What? WHAT?? Wait a minute, what happened to the mortuary? Didn't they used to put dead people in the mortuary? Since WHEN are these people getting hotel rooms?
Tom: It's in...
Whoopi: What's happening in America? Giving dead people hotel rooms? They can't even watch the satellite! (Tom and audience laugh)
Smokey Robinson: You know, they're check...they're checking in rather than checking out (Tom and audience laugh again)
Check Your Oil? (November 17, 1999)
Tom: Reuters reports that in Beijing, the "Bang-Bang Peace and Happiness Health Center" is China's first licensed what?
Kevin James: Jiffy Lube (Tom and audience laugh)
Whoopi Gets Bleeped (February 17, 1999)
Tom: Rush Limbaugh's second book has sold over 9 million copies and is called...
Whoopi: I'm a big ol' [bleep]
Shoot! (February 17, 1999)
Richard (overly excited): This is for the win! For the win! Gimme a "W", gimme an "I"...
Caroline: Gimme a gun! (Tom and audience laugh)
Gilbert Strikes Again (January 28, 1999)
Tom: A study published in the recent issue of the British Medical Journal claims the age-old prejudice people have about doctors' what is true?
Gilbert: Two words. Rectal Examination! (Tom cracks up)
He Shoots, He Scores (February 22, 1999)
Tom: Hockey is the national winter sport of Canada. What is their official summer sport?
Jeffrey Tambor: Waiting for hockey
An Homage to Mike Tyson (February 23, 1999)
Tom: Who's known for his "Self-Portrait with Bandaged Ear"?
Deborah Norville: Evander Holyfield
Tom: It is the highest point in South America, Titicaca is Peru's biggest what?
Whoopi: You're letting me say "Titicaca" on television?
Gilbert Gottfried's Pants (February 23, 1999)
Tom: In folklore, where would you find a "jolly roger"?
Gilbert: In my pants
Gilbert: IN MY PANTS!
Tom: I know
Gilbert: I just felt like saying it again
Whoopi: Katarina Witt was in your pants?
Gilbert: Oh, I only pray
Tom: Leslie Visser is the first what to announce for Monday Night Football?
Gilbert: The first sportscaster without a really ratty toupee. Or...IN MY PANTS!
Gilbert: Did I say "In my pants?"
Tom: I think you did...figurative speech of course...Who is obsessed with squeezing toilet paper?
Gilbert: That's me, and it's not an obsession, it's a hobby! What I want to do in my spare time is my business
Tom: What debuted in 1936, Whoop, with a cover picture of an obstetrician slapping a newborn baby and the caption "Life begins"?
Whoopi: The first sexual harassment suit. But if it wasn't that, and it wasn't in Gilbert's pants...
Gilbert: Heh, IN MY PANTS!
Tom: You know, somewhere a therapist is getting very rich off him
Gilbert Gottfried's YOU FOOL Bluffs (October 1, 1999)
Tom: Playgirl magazine's clinical sexologist says "I think we should be able to talk about sex the way we talk about" what?
Gilbert: Soft-boiled eggs, cause they both take under three minutes
Tom: In a poll, 94% of Hungarians compared to only 48% of Americans said doing this was necessary to feel fulfilled. Doing what?
Gilbert: Seeing Wayne Newton live
Tom: This happened first season too, didn't it? When she heard that Phileas Fogg had done it in 80 days, journalist Nellie Bly beat him by doing it in 72 days. What did she do?
Gilbert: Get through to the cable company!
Tom: Its French designers nicknamed it the "atom" because of its small size and the explosive effect a woman would have when she wore it. Today it's better known as...
Gilbert: It's in my pants!
Bruce: But your thumb's covering it
Gilbert: In fact it's covering it right now
Tom: What significance does 1908 have if you're a Chicago Cubs fan?
Gilbert: Uh, that's the year you were in Chicago!
Tom: Steve Austin is a big, bad professional wrestler fully known as...
Tom: The word "smog" comes from what two words?
Gilbert: Uh, smelly fog
Why some of the Survivor 1 cast didn't show up for their theme week (September 25-29, 2000)
Sean: too busy explaining his alphabet theory on Sesame Street
Greg: CBS security dragged off some surfer talking into a coconut shell
Kelly: still waiting by the side of the road for Susan to give her a drink of water
Rudy: in a glass-chewing competition with G. Gordon Liddy
From One Host To Another (December 14, 2002)
Peter Marshall: They are the biggest distributor of hamburgers in the world, who are they?
Tom: That's easy, it's Marlon Brando
The Joke's On You (April 1, 2003)
Co-executive producer Henry Winkler let fans in on a little secret, he was playing an April Fool's joke on Tom. The day's real players were secluded while actors took their places, and their performances were very believable. The female actor kept weeping uncontrollably, while the male actor was annoyed by her and got Tom annoyed at the same time (Henry at this point was taking the fans through the process of the prank via video commentary). When it was starting to get out of control, Henry called an end to the joke by announcing "Tom, April Fool's!" A shocked Tom received loud applause and shouts of laughter from the entire studio, before announcing to the world "That was [bleep]ing brilliant!" This was one of the funniest and most priceless moments of Season 5, if not the whole series!
I'm always looking for more funny moments from Seasons 2, 3, 4, and 5. If you've got a bluff, blunder or wacky moment you'd like to share, please e-mail me.