On top of that, any shortcomings of the celebrity players were compounded by the format: less time per subject in the front game, so if you didn't get it straight off you were screwed; no returning champions, so players were never able to play with the celebs long enough to get on a wavelength; and the conditions to get in the tournament, which put enormous pressure on both sides in the Winner's Circle (to go along with the esoteric writing therein).
Donnymid's problems, in a nutshell -- minus the strict Winner's Circle judging, which required the guesser to say the subject title nearly-verbatim. For some reason, simply uttering the "essence" of the subject (which awarded the box to the contestant in the classic era) was usually not accepted:
* Subject: "Characters from
The Wizard of Oz"
* Guess: "Things from
The Wizard of Oz"
* Ruling:
NOT ACCEPTABLE* Subject: "Things Mick Jagger Would Say"
* Guess: "Mick Jagger"; "I am Mick Jagger"
* Ruling:
NOT ACCEPTABLE* Subject: "Things A Baby Sitter Says"
* Guess: "Things A Baby Sitter Does"; "Baby Sitter"
(latter phrase repeated several times)* Ruling:
NOT ACCEPTABLEAs for qualifying for the Tournament, those rules and the lack of returning champions basically sapped all the fun out of both contestants winning $10,000 -- it turned such an event from "Rematch next time!" into a wash. And some days, especially during Season 2, it just wasn't possible to clear at least one of the Winner's Circle rounds.
(First and third examples were eventually guessed verbatim, and the former ended with a $10,000 win; second example was passed upon and not returned to before time ran out. First two examples are from Donnymid Season 2, while the third is from a first-person report {written, at least in part, by the dearly-missed Randy Amasia} following the taping of the infamous 1996 Pilot; it seems both shows had the same judge.)