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- At least twice, a contestant guessed a word before their partner had given a clue ("chameleon" in "Things That Change Color" and "culture" in "Things Associated with Yogurt"). The latter one stunned Dick Clark, who looked around the set in amazement.
- Any time the sixth category in the Winner's Circle is guessed just as time expires. In the 80s versions, Dick will ask for an angle of the clock as an indication of a really close win.
- A few times, a team ended up with 5/6 in the Winner's Circle due to a clue being deemed illegal...but upon the return from commercial, the judges discovered that the clue was acceptable after all, leading to a win. For instance:
- This example from 1983, where Levar Burton is buzzed for saying "10 Across" on the box "Things in a Crossword Puzzle" but gets the other five boxes. After they come back from commercial, Dick announces that they have overturned the call, since "across" and "crossword" are not etymlogically related, leading to a $10,000 win.
- This one from 1987. Marcia Wallace gets buzzed for saying "A bat" on "Things That Get Hit" after clearing the other five boxes. Come the commercial break, Dick reveals that he has discussed with the judge, and that they have decided that the clue is valid after all for $10,000.
- March 26, 1973: The first Winner's Circle on the first show gave away the first $10,000 check to the first undefeated champion (with the help of Rob Reiner). Series creator Bob Stewart said the CBS execs present for that taping demanded the show be canned when this happened, arguing there was no way the game wasn't staged. Reiner mentioned the win in the opening segment of the third episode (which exists), confirming the moment in a contemporary fashion.
- 1973-74: Every $10,000 win shown in not only the Television City openings, but also the $25,000 pitchfilm.
- Any $25,000 win, including both of Dick Clark's appearances.
- December 2, 1977: Billy Crystal's 26-second blitz through the Winner's Circle, giving only one clue for each box. Made even more amazing through some rather unusual chains of thought — would you have gotten "Things in a Barrel" if given the clue "monkeys", or "Things That Are Wilted" given the clue "old flowers"? Amazingly, his record has stood the test of time — as of the current revival, Crystal's time still hasn't been beaten.
- The full Winner's Circle round, slightly longer than the above clip, was reran on April 30, 1979 note ; when GSN began to air the 1970s Pyramid, it was discovered that the original episode (minus the 36 seconds reran in 1979) had been destroyed by ABC.
- Although no copies exist of the actual episode, Mark Guerra, a huge fan of the 70's era of Pyramid, was able to record it on audio tape back in the day. Not only was there a record-breaking win for Crystal's partner, Natalie Hearst, but early in that same episode, Lynn Redgrave (the other celebrity for that week) won $20,000 for a woman named Nora. Below is a transcript of what transpired after Crystal and Hearst celebrated the win.
Dick Clark: Bob ...
Bob Clayton: I think that's a record.
Dick Clark: That is a record all-time win, 26 seconds to go to the top. [applause] Fantastic. Look at that. That doesn't happen in that length of time. Pem, Pem, Pem, Murdock hello, how much time do we have? 40, 20 seconds?
Natalie: Oh, can I go back and go for another 10? [laughter]
Dick Clark: What are you going to do with all the money?
Natalie: First pay off some debts and then maybe go to graduate school.
Dick Clark: Have we given away $30,000 today? Holy mackerel! We'll be back in a second with both winners, don't go away.
[the music continues along from where it had stopped and as they go to commercial. As they return and the edited version of "Tuning Up" ends...]
Billy Crystal: I'm just realizing what we did. One clue.
[Upon returning, there was a flashing $30,000 sign on the screen]
Dick Clark: Natalie and Nora you've won $30,000, do you have a word for us?
Both: Thank you!
Dick Clark: See you the next time.
- September 4, 1978: Robert Walden helped two contestants win a combined $30,000 in one day. That's $20,000 in the first Winner's Circle, and $10,000 in the second Winner's Circle.
- Both $50,000 wins.
New $25,000 (1982-87, 1988)
- There were a couple of times when the contestants played to two consecutive 21-21 ties, and only one of the players won both tiebreakers. The losing contestant didn't go home empty-handed, though...for playing to two straight perfect game ties, that contestant won a trip to Bermuda.
- June 29, 1983: A contestant gives the clues to both Deborah Adair and Terry Lester during their respective Winner's Circles, winning $25,000 in the process. For Adair's, this was her first time in the Winner's Circle, and for Lester's, they won at the very last second, as Dick had to check with the judges to make sure they got it in time.
- July 13, 1983: You have to hand it to Michael J. Fox and his partner for going through a triple tiebreaker AND THEN, with no rest, winning ten grand on the Pyramid.
$100,000 (1985-88, 1991)
- Every $100,000 win. The first nine had the audience emptying onto the stage, swamping the winner and getting their face on TV.
- Perhaps the most awesome $100,000 win of all is the one that lasted all of 27 seconds from September 1987.
- The best reaction that a winning contestant can give is probably the very same look you give when you're about to shit your pants after winning $100,000!
- Another great reaction, this one from celebrity Mary Cadorette after she helps a contestant win $100,000.
- To date, Keefe Ferrandini is the only contestant to give clues in the Winner's Circle and win the $100,000.note She even qualified the exact same way after nearly getting eliminated from tournament qualification. Basically, if she's going for the top, she's doing it in Curb Stomp fashion.
- Shelley Smith holds the distinction of being the cluegiver for two $100,000 wins, the first in November 1985 and the second in November 1986.note
- The fact that this version awarded the franchise record total of $150,800, a record that can never be broken, as winning the Winner's Circle twice in the current version only awarded $150,000.
- Any $25,000 win, which was not easy due to a lack of returning champions, the anal judging, and the esoteric categories.
- One Winner's Circle had the category "Fattening Things". The contestant kept saying "Fattening Foods" but due to the rule were contestants had to say the category verbatim, the judge wouldn't take it. Time ran out and, upon being told by Donny what the category was, the contestant and the celebrity engaged in a shouting match with the judge. Eventually, the judge backed down and the contestant won.
The Pyramid (2012)
- In general, any Winner's Circle win. Why, especially, because they brought back the 80s winning dings and the $100,000 Pyramid theme.
ABC $100,000 (2016-present)
- The third episode featured the version's first $100,000 win; there would be one more in season 1, and a $100K win to start season 2.
- Not only did the third episode of Season 2 have two $100K wins in each half, but the second also had the first double WC win for a maximum of $150,000.