Considering the tense format of Pyramid, great moments occurred many times.
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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, who looked around the set in amazement.
A few times, a team ended up with 5/6 in the Winner's Circle due to a clue being deemed illegal...but upon coming back from commercial 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 Stewartsaid 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 $25,000pitchfilm.
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 (a week featuring Crystal and Sal Viscuso, who were good friends and playful "rivals"); 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.
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.