- 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; 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!" - Funny Moments:
- 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.
- Hilarious in Hindsight: One 2000 episode parodied Who Wants to Be a Millionaire?, 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, ABC revives the format, broadcasting it as its original primetime format, with Kimmel as host... and contestants can now ask for Kimmel's help as a lifeline.
- Ho Yay: Plenty between Ben and Jimmy. Played for Laughs, of course.
- Replacement Scrappy: Nancy Pimental and Sal Iacono. Neither had 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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