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- At least twice, a contestant guessed a word before their partner had given a clue ("culture" in "Things Associated with Yogurt" and "chameleon" in "Things That Change Color"). The first time 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.
- 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.
- 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.
- 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.
- 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. 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.
- 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.