Win Ben Stein's Money

A Game Show produced for Comedy Central in the late 1990s, hosted by deadpan actor and former political speechwriter Ben Stein, and featuring radio personality turned late-night Talk Show host Jimmy Kimmel as The Announcer. Using the common "quiz show" game model, and sporting a humorous atmosphere (as befitting a Comedy Central program), the show might have been forgotten as merely another Jeopardy! clone if not for its unique concept — the contestants really were competing for Stein's money.

The show offered a $5,000 prize pot which constituted Stein's paycheck for each episode, of which the contestants tried to earn as much as they could; the remainder of the pot went home with Stein, so in a very real sense contestants were taking money out of Stein's pocket. (Of course, Stein was also paid a normal salary on top of his "winnings".)

The program featured another unique conceit: Since his own paycheck was at stake in each episode, Stein would actually turn the hosting/moderating duties over to Kimmel during the game's second round and would join the contestants as a contestant himself. The Bonus Round featured the winning contestant going head-to-head with Stein in a "Best of Ten Test of Knowledge", a timed rapid-fire questionnaire. Stein was no slouch as a contestant; highly competitive (especially when defending his earnings), he regularly trounced the actual contestants and rarely gave a wrong answer — although there were quite a few times when he lost the entire $5,000 pot to some "superior intellect", as he would say.

Kimmel was eventually replaced by Nancy Pimental, and later by Kimmel's own cousin, Sal Iacono. The show ceased production in 2003.

Game Show Tropes in use:

Bonus Round: The Best of Ten Test of Knowledge. If the player lost, they only kept any money they won previously. If there was a tie, the player would win $1000 in addition to the money they've already earned. If the player wins, they get all $5000 of Ben Stein's money.
Confetti Drop: If the contestant beat Ben, money fell from the ceiling.
Double the Dollars: From $50-$150 per question in Round 1, to $200-$500 in Round 2.
Personnel:
- The Announcer: Jimmy Kimmel is the most well-known.
- Game Show Host: Ben Stein. After Round 1, The Announcer would host for the remainder of each show while Ben lowered himself down to being "a common contestant".
- Lovely Assistant: Nancy Pimental technically counts.
- Studio Audience
Sound Proof Booth: Where the contestant and Ben sat during the bonus round. Ben's room was an upper-class library, while the contestant's room was barren.

Tropes used in Win Ben Stein's Money include:

Actor Allusion: One contestant was stumped and instead answered "Bueller...Bueller" in reference to Ben's previous role as the teacher.
Author Tract: Whenever Richard Nixon was mentioned, Stein (who was a speechwriter for him) would usually say a word or two to defend him.
Berserk Button: Never accidentally answer by using "What is".

Ben: Not "what is"! This isn't Jeopardy!
Jimmy: That is the cardinal sin; does he look like Alex Trebek to you?!

- Violators had to wear a Dunce Cap until the next commercial break.
Catch Phrase: Of sorts. When Ben lost the Bonus Round (very rare), he would say to his opposition "I bow to your superior knowledge! (bow) I'm humbled! I'm impressed! I hate you! Get outta here!" — and then hand that contestant that hard-won $5,000.
A Day in the Limelight: Ben and Jimmy once swapped their traditional duties for an episode.
Deadpan Snarker: Ben Stein.
Exactly What It Says on the Tin: It's a game show hosted by Ben Stein, and you're literally trying to win his money.
Name's the Same: Once did an episode where all three contestants were also named Ben Stein.
Nintendo Hard: Ben Stein is smart.
Oh Crap: The look on Ben's face when he got a question wrong, occasionally resulting (especially during the Bonus Round) in a Precision F-Strike...although perhaps not that explicit.
Twice An Episode: Ben Stein often puts the money back in his vault via...interesting methods.
One Steve Limit: One episode averted this by having three contestants who were all named Ben Stein (labelled as Ben #1, Ben #2, and Ben #3). When the second round came about, the podium occupied by Ben Stein (the host) had name "Big Ben".
Opening Narration:

Hello, I'm Ben Stein. And today, I'm making history. I'm putting up $5000 that says I know more than you. So if you're smart enough, fast enough, and if you've got the guts, you can Win Ben Stein's Money!

Public Domain Soundtrack: The theme song is "Ode to Joy", and the transition music consists of various classic tunes, such as "Eine Kleine Nachtmusik", "Ride of the Valkyries", "Russian Dance", and "Water Music".
Rule of Funny: Many of the categories.
Running Gag: Several.
- Many contestants answered in the form of a "What is...?" question, either by accident or just to cheese off Ben. In either case, he'd respond by forcing said player to wear a dunce cap for the remainder of that round (except on the rare occasion where the contestant caught him/herself in the process).
- When Ben asked Jimmy to explain the Bonus Round rules, the response would be something akin to "Yes, Nipple Nuts".
- If Ben was asked the questions second in the bonus round, Jimmy would ask an eleventh question if time had not expired. Two such examples:

Jimmy (if Ben won): Would you like to cuddle after the show?
Jimmy (if Ben lost): How does it feel to lose $5,000?

Smart People Know Latin: One of the categories is called "I speak Latin, ergo I am annoying."
Those Two Guys: Ben and Jimmy played off each other quite well.
Trans-Atlantic Equivalent: Win Jeremy Beadle's Money aired on Channel Five from 2 August to 22 December 1999. Appropriately, Beadle was just as Nintendo Hard as Stein.
Unwinnable by Design: On Ben's end. In the first round, the contestants can take his money unchallenged, which means that unless they all totally blow the first round, Ben's going to lose at least part of his $5,000.