YMMV / Win Ben Stein's Money
Quite a few during the Jimmy Kimmel era.
In general, whenever a contestant accidentally responded in the form of a question, which prompted an uproar in the studio as Ben Stein whipped out a Dunce Cap for the offending contestant.
Awesome Moments: Those who won the $5,000 earned every penny — including one who went a perfect 10-for-10 against Ben's 9-for-10. (The same episode also features Ben and Jimmy dropping their pants after the contestant won the Bonus Round on a bet.)
"I am humbled, I hate you, get out of here! You've done enough damage!"
Replacement Scrappy: Nancy Pimental and Sal Iacono.
Both lacked the chemistry Kimmel had with Ben. Nancy in particular was not well suited to the banter Ben had been exchanging with Kimmel. The previously funny insults that were just part of the show now came off as more mean-spirited.
What an Idiot!: This answer:
Ben: In Ben Franklin's kite-flying experiment, what object was tied to the string of the kite?
Contestant: The antenna of his house.
"Ben puts down his question card and does a scowl and
towards the contestant": What kind of antenna do you think?
Jimmy: His satellite dish!