The Classic Hollywood Squares Site

Square Rules
"I'll take Charley Weaver to block..."
The Hollywood Squares was a tic-tac-toe game with celebrities in the grid.  That's the short version.  The actual game was a little more complicated...

Peter Marshall would ask a question of a celebrity ("Paul, in what state was Abe Lincoln born?"), who, of course, would make a joke first ("Like the rest of us, naked and screaming!") then either give the real answer (Kentucky) or
a fake, "bluff" answer (he actually said Illinois that night in 1968).  The contestant would have to decide whether he/she agreed or disagreed with the given answer.  If the contestant is right, his "X" or her "O" goes in that space; if he or she wrong, the opponent gets it.  The exception is if the square would lead to a win (i.e., if the first contestant was trying to block).
    There were no "cat's games" on The Hollywood Squares; if no one got three in a row then the first contestant to get five squares won the game.  They played best two out of three, and the winner of the "match" would come back to meet another contestant.  Each game was worth $200; each match $400.   After five matches the contestant got a prize package that included a car, and would be retired.
The nighttime version was slightly different, since the unfinished game would not resume the next day (most stations ran the two episodes on non-consecutive days).  So each game was worth $250.  If that ear-shattering, heart-stopping air horn sounded, the current question was finished and each contestant got $50 per square already on the board.  The winner of that episode won a car.
There was also a Secret Square game in which the contestant who picked the Secret Square won a prize package.  It was the first complete game on the daytime version and the first three games on the nighttime version.  The celebrities (like Michael Landon, pictured here in 1968) were usually discouraged by the producers from coming up with "zingers" during Secret Square questions, since so much was on the line, and most of the questions were multiple choice anyway.  (That still didn't stop Lynde or, say, Oscar the Grouch from cracking wise during Secret Square time on occasion.) 
The show was on the air a good ten years before the producers ever added an end game.  The contestant simply picked a star, who read what was in an envelope.  It could be $5,000 but was always a nice prize anyway, so there was no real way to lose here.  The message in the envelope was always written like a bizarre riddle; often the contestant would be prepared to win a small prize only to win the full $5,000.  
One of the show's most controversial policies was that they often briefed the stars on topics in advance.  They didn't always get the question, but their writers often had a ready-made bluff waiting for them.  Some insisted on winging it all the way (Abby Dalton, for instance) but others had gag answers written well in advance...including Paul Lynde (who could still ad-lib every now and then).  The reason the show got around this, barely more than a decade after the quiz show scandals, was that the contestants themselves had no way of knowing the questions or the answers in advance, and the celebrities weren't exactly "spoon-fed" the answers as some believe (and also believed about Celebrity Sweepstakes).
Peter Marshall: Can't put an "X" there, you'll have to earn that one yourself...
Peter Marshall:  This is for the win...
--what Marshall said after a contestant picked what would be the third square in a row if the answer is correct, and reportedly the basis for the modern day internet expression FTW when it means "For the Win" and not the other thing
"The areas of questions designed for the celebrities and possible bluff answers are discussed with some celebrities in advance.  In the course of their briefing, actual questions and/or answers may be discerned by the celebrities."
--disclaimer that ran in the closing credits of each broadcast
(Reading of the bonus prize after player won the match)
David Brenner: Here's the news, do you ride a bike?
Peter Marshall (to contestant): Do you ride a bike?
(contestant nods)
Brenner: You do? Good, because in Yugoslavia your prize would be called, "Five thousand American dollars."
(contestant freaks out; Marshall counts off five one-thousand-dollar bills)
(Sesame Street's Oscar the Grouch is the Secret Square, and the contestant wins)
Peter Marshall: Oscar, you've made a man very happy...
Oscar: I'm sorry to hear that.
(Oscar is the Secret Square again in the same show and this time the other contestant wins)
Peter Marshall: Oscar, aren't you proud again? You've made a woman happy...
Oscar: No!  I'm not supposed to
help people! (groans)
(Big Bird is picked and turns out to be the Secret Square)
Peter Marshall: Did you ever dream that one day you'd be worth 94 hundred dollars?
Big Bird: Gee, and I was excited about 63 cents!
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