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* SugarWiki/AwesomeMoments: Those who won the $5,000 ''earned every penny'' — including one who [[https://www.youtube.com/watch?v=JhpO7nMBTdg went a perfect 10-for-10 against Ben's 9-for-10]]. (The same episode also features Ben and Jimmy [[SugarWiki/FunnyMoments dropping their pants]] after the contestant won the BonusRound on a bet; the contestant involved, at the urging of Ben and Jimmy, also dropped his pants.)
-->"I am humbled, I hate you, get out of here! You've done enough damage!"
* SugarWiki/FunnyMoments:
** Quite a few during the Jimmy Kimmel era.
** In general, whenever a contestant accidentally responded [[Series/{{Jeopardy}} in the form of a question]], which prompted an uproar in the studio as Ben Stein whipped out a DunceCap for the offending contestant.
* HilariousInHindsight: One 2000 episode parodied ''Series/WhoWantsToBeAMillionaire'', with Jimmy offering his help as a way to help the contetants cheat in the second round. Within eleven months of ''Millionaire''[='=]s syndicated run ending in May, 2019, Creator/{{ABC}} revives the format, broadcasting it as its original primetime format, with Kimmel as host... [[IronicEcho and contestants can now ask for Kimmel's help as a lifeline]].
* HoYay: Plenty between Ben and Jimmy. PlayedForLaughs, of course.
* ReplacementScrappy: Nancy Pimental ''and'' Sal Iacono. Neither had [[VitriolicBestBuds the chemistry with Ben that Kimmel had]], and the previously funny insults and banter between Ben and the host that were part of the show's humor now came off as mean-spirited.
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