Considering the tense format of Pyramid, great moments occurred many times.
- 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 asks 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 "34 Across" on the box "Things in a Crossword Puzzle" but gets the other five boxes. After they come back from commercial, Dick announces that, since "across" and "crossword" are not etymlogically related, they won the $10,000.
- June 2, 1983: Barry Gordon says "Canadian policemen" for "Things That are Mounted" and gets the buzzer. After the commercial break, Dick explains that the judge chose to overturn the buzzer because they were expecting "mounted" in the sense of a mounted deer head, without realizing that Gordon's clue was legal for describing a policeman mounting his horse.
- This one from 1987. Marcia Wallace gets buzzed for saying "A bat" on "Things That Get Hit" after clearing the other five boxes. Notably, Dick disputed this one himself — when the judge said "You don't hit a bat", Dick replied "you hit a bat with a ball." After the commercial break, he revealed that the judge chose to give them the money after deciding that yes, a bat can be hit by the ball.
- 1987: Mary Cadorette's clue "magnets" was buzzed for the fifth box "Attractive Things" as her partner guesses the subject. They then get the sixth right away, prompting Dick to have the judge check the offending clue during the break. It turns out magnets not only attract, they can also be attractive; the contestant wins $25,000.
- 1987: Allen Kayser was conveying the subject "Things You Count With". It sounded to Dick that he had said "In your mind", which was illegal. The contestant got the last subject with 22 seconds to spare... but Dick silenced everything and they went to break. Returning from break, Dick quieted the music down and had a long talk with Allen and the contestant. We learned that Allen was from Colorado. Dick noted that if he had said "and your mind", it would have been accepted. The judges checked the tapes several times and heard a "d" every time, so the contestant won $25,000.
- During a Soap Opera week, one actor gave the clue "a leaky pipe" for "Things That Drip" which got buzzed but the pair got the other five subjects. Dick consulted with the judge and during the break they determined the clue was not synonymous (the clincher being that neither "leak" nor "drip" was listed as a synonyms for each other in the dictionary), so their charity won $10,000.
- A variant occurred on September 4, 1985. After clearing the first five boxes, Charlie Siebert gets the buzzer for saying "What you do to a loan" on the box "You pay interest on it." When he points out that he was confused by the wording of the box, Dick and the judge decide to take his side and slot in a new box for him to play with the remaining time. He successfully conveys the new box "Things that have a pattern" for $10,000.
- In the 80s versions, any time a contestant wins $5,000 for breaking a 21-21 tie.
- March 26, 1973: The first Winner's Circle on the first show gave away the first $10,000 check to the first undefeated champion. Rob Reiner's winning clue was "a doughnut" for "Things With a Hole". 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.
- June 1973: Richard Deacon is describing "Things you wrap", but the judge doesn't accept "Things you unwrap" or "things you put wrapping paper on". As he had gotten the other five boxes, the judge decides to swap out the box for a new one. Richard successfully conveys "Things at a party" to win the $10,000.
- Any $25,000 win, including both of Dick Clark's appearances.
- The pitchfilm has Bill Cullen talking about the excitement of contestants winning big on $10,000 accompanied by clips of Winner's Circle triumphs.
- 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 rerun 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.
- Both $50,000 wins.
- 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.
- September 22, 1982: Constance McCashin winning $10,000 for two contestants on one show. The first stands out for a few reasons:
- It was the first time the Winner's Circle is won on this version.
- Constance received the clues.
- She gets the last two subjects with only one clue: "Midnight Cowboy" for "Dustin Hoffman Movies" and "a Popsicle" for "Things on a Stick". The time's up buzzer starts sounding right after she says "stick".
- Week of October 11, 1982 and April 22, 1983: Two contestants win $25,000 despite the same misspelled category in the Winner's Circle: "Anthing with a Collar". It's not noticed the first time, but it is after the second. Dick lets the second contestant keep the slide◊ with the misspelling as a souvenir.
- Week of October 18, 1982: After winning $25,000 for a contestant, Nipsey Russell runs a victory lap around the Winner's Circle.
- 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.
- 1988: Kelly Grogan becoming the daytime record holder the hard way. Shortly after The $25,000 Pyramid began its three-month return on CBS, Kelly made it to the Winner's Circle having already won $31,100. She got the top category "Things You Abandon" after Earl Holliman said "A basketed baby", but the audience cheered so loud that no one could hear the illegal clue buzzer. When the show came back, Dick explained that Earl's clue was a made-up expression which negated Kelly's $10,000 win. Her opponent bested her score with $800 to her $750, seemingly ending her run. Fast forward ten weeks, and Kelly is invited back. She announces her total as $41,100, meaning the judge overturned the loss. She eventually won $60,050, ending her run on Monday of the final week.
- Date unknown: During one Winner's Circle round, Jamie Farr helps a contestant named Patty breeze through the first five topics in roughly thirty seconds. Then comes "Words With a Hyphen" at the top. Jamie freezes, only offering one full clue with "Neo-Roman". Somehow, as Jamie's about to say "black-market", Patty squeezes in "Hyphen?" with literally one second to spare. Reluctant to celebrate after hearing "hyphenated words", Jamie looks toward the judge, although the bell is repeatedly ringing symbolizing a win.Farr: How did you get that? The idiot sitting there couldn't come up with anything!
Dick: It just came to you? I didn't even hear it happen.
- 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
- May 1991: One contestant goes for $100,000 with Hillary Bailey Smith giving the clues. They reach the top category "Things That Stick Out" with a few seconds to spare. The contestant says "Things That Stick" and Hillary screams, thinking they've won. Time expires and John, after a Rapid-Fire "No!", explains that the contestant needed to say the other word "Out" to win. All is not lost as the same contestant makes it back to the Winner's Circle in the second half where she does win the $100,000 with Barry Jenner.
- Week of March 30, 1987: On one show, Nathan Cook wins $10,000 for two contestants, and they both qualify for the tournament. In the second Winner's Circle, the contestant gets the last subject "Things You Gather" with one clue: "Your thoughts."
- 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.
- In general, any Winner's Circle win. Why, especially, because they brought back the 80s winning dings and the $100,000 Pyramid theme.
- 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.
- The third episode of Season 2 had two $100K wins in each half.
- Anytime somebody wins the maximum $150,000, such as this occasion.
- One player had such a lead that the other had no way to catch up.
- The way the Winner's Circle begins. Everything changes color to red and black and a cluster of spotlights swirl directly onto the Winner's Circle as the camera zooms in from above.