[[caption-width-right:260:It's ALL about the Benjamins.]]A GameShow produced for Creator/ComedyCentral in the late [[TheNineties 1990s]], hosted by [[DeadpanSnarker deadpan actor]] and former political speechwriter [[Film/FerrisBuellersDayOff Ben Stein]], and featuring radio personality turned late-night TalkShow host Jimmy Kimmel as TheAnnouncer. 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 ''Series/{{Jeopardy}}'' clone if not for its unique concept [[ExactlyWhatItSaysOnTheTin the contestants really were competing for Ben 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".) [[note]]Valleycrest, the producers of the program - the same people who produced the American version of ''Series/WhoWantsToBeAMillionaire'', and a division of Buena Vista Television, which was in turn a division of Disney (it was renamed as Disney-ABC Domestic Television in 2007) - set a prize budget for each season. If anything was left from that at the end of the season, Ben got to keep it. If the contestants were better than expected, and the prize budget was exceeded, then it was Valleycrest/Buena Vista/Disney, not Ben, that paid out the overage.[[/note]]

The program featured another unique conceit: Since his own paycheck was at stake in each episode, Stein would actually turn the [[GameShowHost hosting/moderating duties]] over to Kimmel during the game's second round and would join the contestants as a contestant himself. The BonusRound 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 [[SuspiciouslySimilarSubstitute replaced]] by Nancy Pimental, and later by Kimmel's own cousin, Sal Iacono. The show ceased production in 2003.

Also see ''Series/TheChase'', which also requires players to outsmart a '''highly''' intelligent trivia expert to win money.
!!GameShowTropes in use:
* AllOrNothing: At the end of the first two rounds, the contestant with the lowest score is eliminated and any money they earned is taken away and returned to Ben Stein's Prize Pot. Averted with the last remaining player, who got to keep any money they already earned regardless of the outcome of the Best of Ten Test of Knowledge.
* BonusRound: 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 $1,000 in addition to the money they've already earned. If the player wins, he/she won what remained of the $5,000 pot. In at least one "champions" episode, the pot was upped to $25,000, and the contestant who faced off against Ben for it [[spoiler:ended up winning the money, taking his total amount of money won from Ben to $30,000.]] [[note]] (Theoretically speaking, Ben's remaining stash could actually be LESS than the contestant's take during the first two rounds.)[[/note]]
* ConfettiDrop: If the contestant beat Ben, money fell from the ceiling.
* DoubleTheDollars: From $50-$150 per question in Round 1, to $200-$500 in Round 2.
* Personnel:
** TheAnnouncer: Jimmy Kimmel is the most well-known.
** GameShowHost: Ben Stein. After Round 1, TheAnnouncer would host for the remainder of each show while Ben lowered himself down to being "a common contestant".
** LovelyAssistant: Nancy Pimental ''technically'' counts.
** StudioAudience
* PromotionalConsideration: From the show's second season onward.
* RulesSpiel
** Round 1:
--> '''Ben Stein''': All right, contestants. In the first round, questions are worth anywhere from $50-$150 of my money. Now every time you manage to answer a question correctly, you win money, and I lose it.
** Round 2:
--> '''Jimmy Kimmel:''' Now we'll see just how smart Ben really is as we play more of "Win Ben Stein's Money".\\
'''Ben Stein:''' Welcome back. As this rounds begins, Troper 1 has $ of my money, Troper 2 has $ of my money, and I have a mere $<5,000-(x+y)> remaining of my original $5,000 stake, which I will now defend by becoming a common contestant!\\
'''Jimmy:''' From this point forward, Ben has no advance knowledge of any of the questions to be asked. Isn't that right, Ben?\\
'''Ben:''' That is right, Jimmy. It's also right--well, it's not ''right'', but it's a ''fact''--that the questions in this round have risen to the level of $200-500 of my money, that is if '''you''' get them right. If '''I''' get them right, my total stays the same, but thankfully, [[DepartmentOfRedundancyDepartment none of my money is taken away]].\\
'''Jimmy:''' And whoever has the higher score at the end of this round, whether it's Troper 1, who starts [[Administrivia/EditWar edit wars for fun]], or Troper 2, who had his [[TVTropesWillRuinYourLife life ruined by TV Tropes]], will go on to play against Ben one-on-one for $5,000 of his money. Let's have a look at our topics. They are...
** Bonus Round:
--> '''Ben:''' So far, you've managed to take $ away from me, and that is yours to keep, no matter what happens. But now you have a chance--albeit a small one--to walk away with all $5,000 of my money, which Jimmy is now wheeling towards us in this safe. And all you have to do is beat me in what we call the "Best of Ten Test of Knowledge." Would you explain it to the group, please, Jimmy?\\
'''Jimmy:''' Yes, . I'm going to ask and Ben the same ten questions. , if you can answer more correctly than Ben can, you get his $5,000. Would you like to go first or second?
* SoundProofBooth: Where the contestant and Ben sat during the bonus round. Ben's room was an upper-class library, while the contestant's room was a barren cell.
!!This show provides examples of:
* AuthorTract: Whenever UsefulNotes/RichardNixon was mentioned, Stein (who was a speechwriter for him) would usually say a word or two to defend him.
* BerserkButton: Never accidentally answer by using "What is...?"
-->'''Ben:''' Not "what is?"! This isn't ''Series/{{Jeopardy}}''
-->'''Jimmy:''' That is the cardinal sin; does he look like Creator/AlexTrebek to you?!
** Violators had to wear a DunceCap until the next commercial break.
* CatchPhrase:
** When Ben lost the BonusRound (which was ''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.
** In the lead-in to Ben's turn at the BonusRound, after being informed of the score he needed to beat, Ben would usually say, "I shall do my best" or "I take all challenges seriously".
** Occasionally in the Best of Ten round, when told that the contestant had scored less than five points, he would say, "I take all challenges seriously."
** At the end of Round 1, Ben would say to the viewers "I am going defend my money by becoming a common contestant. Stay tuned, you might learn something!"
** After coming back from the first commercial break, he would usually say "We're back, with more of Win MY--Ben Stein's--Money."
** Before Round 2, Jimmy would say "Now we'll see just how smart Ben really is as we play more of ''[[TitleDrop Win Ben Stein's Money]]''."
** Often, during the Best of Ten Test of Knowledge, when the contestant goes first, Jimmy will say to the contestant, "As the host, I'm supposed to remain neutral, but since Ben can't hear me right now, kick his ass."
* CelebrityEdition: Ranged from hosts of other Creator/ComedyCentral programs, to political commentators, to porn stars.
* {{Cosplay}}: Ranged from TV shows (including ''Series/GilligansIsland'') to political figures (with Ben in drag as First Lady Barbara Bush).
* DareToBeBadass[=/=]ThrowingDownTheGauntlet:
** The OpeningNarration from Stein.
-->'''1998-2001:''' Hello, I'm Ben Stein. And today, I'm going to make history. I'm putting up $5,000 that says I know more than ''you''. ''So if you're smart enough, fast enough, and if you've got the '''guts''', you can '''''[[TitleScream Win Ben Stein's Money]]'''!\\
'''2001-2003:''' "Hello. I'm Ben Stein. My brain is a miraculous instrument. It contains the information I use to protect my money--$5,000. I'll put it up, but I won't give it up without a fight. But if you're smart enough, quick enough, and lucky enough, you can [[TitleDrop Win Ben Stein's Money]]."
** The Closing Narration too, at least in the early days.
-->''(if the contestant lost or tied in the Best of Ten Test of Knowledge)'' That means today, I have successfully defended $ of my money, which I will use to take on my next opponents./''(if the contestant won the Best of Ten Test of Knowledge)'' It's been proven that it can be done. ''(regardless)'' Therefore, I challenge all of you to write, call, or email at futility.com, in the hope, as infinitesimal as it might be, that on some planet on some distant day, you might [[TitleDrop Win Ben Stein's Money]].
* ADayInTheLimelight: Ben and Jimmy once swapped their traditional duties [[http://www.youtube.com/watch?v=8tghGTcyG6Y for an episode.]]
* DeadpanSnarker: Ben Stein.
* DunceCap: A contestant is forced to wear this if they accidentally tag "[[Series/{{Jeopardy}} What is...?]]" to their answers.
* EarlyInstallmentWeirdness: The first season had traditional pull cards for the categories as opposed to being done on TV monitors; the Best of 10 Test of Knowledge had the clock barely displayed on center stage, as opposed to two clocks, one for each booth. Also, the money didn't drop if a contestant won the $5,000 grand prize, and the logo was displayed differently (the second and third words in the center, with the first and last on the top and bottom respectively).
* ExactlyWhatItSaysOnTheTin: It's a game show hosted by Ben Stein, and the contestants are literally trying to win his money.
* FalseReassurance: Inverted. Once Ben Stein steps down to become a contestant, the contestants are reassured that Ben has no advance knowledge of any of the questions to be asked from that point forward.
* FlawlessVictory: The famous episode where Ben agreed to drop his pants if he lost the Best Of 10 saw challenger Bob achieve this by becoming the first person not named Ben Stein to score a perfect 10 in the round, guaranteeing at least a tie[[note]]which would add another $1,000 to Bob's winnings no matter what[[/note]] and forcing Ben to accomplish the same feat, which he failed to do. Cue pants drop.
* FlippingTheBird: Believe it or not, Ben's done this a couple times to the question writers.
* GameShowWinningsCap: With VERY few exceptions, contestants only appeared once, and the most they could win was the complete $5,000 pot. (And with the "Ben Stein's Cup", a single-game tournament which was only played twice for $25,000, the highest a contestant could win was $30,000 altogether.)
* GoldenSnitch: The $400 and $500 questions. Despite the second round's dollar values being much higher than those in the first round, having Ben as a contestant made [[LuckBasedMission come-from-behind victories difficult to accomplish]].
** On at least one occasion, a contestant who was behind by exactly $450 won after responding correctly to a $500 question (which also happened to be the final question of the second round). However, comeback victories like this were ''rare''.
* HeadDesk: One of Ben's reactions to a particularly nasty-sounding category title.
* IronicEcho: In one episode from the show's second season, contestants Jason and Dave are tied at the end of the second round. The sudden-death tiebreaker question deals with one of the major players in American suffrage.
--> '''Contestant Dave:''' Who is... Elizabeth Cady Stanton?
--> '''Jimmy:''' Who is leaving the show, Dave? The answer is you!
* LuckBasedMission: The dollar values are never shown until the topics are chosen. It's not so bad in the first round, but in the second round, any lead of less than $500 can evaporate with just one question.
* NintendoHard: Round 2 and the Best of Ten. Ben Stein is '''smart''', and more worrying, he is ''aggressive''.
* ObviousRulePatch: Originally, the contestants were to receive the full $5,000 prize if the contestant and Ben were tied in the Best of Ten Test of Knowledge. (One early contestant won the $5,000 this way.[[note]]Despite being one of the first episodes taped, the only episode in which this happened aired mid-season.[[/note]]) However, the producers figured out that ties could happen rather frequently[[note]]And in this scenario, it meant that the contestant scoring a 10 was an automatic win for them since it made Ben having to play pointless[[/note]]. As a result, if the contestant ended up tied with Ben, the contestant received $1,000 (which was added to what the contestant had already won).
* OhCrap: The look on Ben's face when he got a question wrong, occasionally resulting (especially during the BonusRound) in a PrecisionFStrike...although perhaps not ''that'' explicit.
** This was another of Ben's many reactions to the really nasty-sounding category names.
* OncePerEpisode: Several:
** Jimmy's, Nancy's, and Sal's humorous introduction for Ben as he walked out on stage.
** Ben calling Jimmy, Nancy, or Sal the to his (such as "the Abbott to my Costello").
** In later seasons, Ben pondering why he's willingly gambling his daily paycheck, then responding to the audience's reaction.
---> '''Ben:''' ...I'm putting $5,000 on the line, and I'm giving these three totally strange strangers a chance to take it all away from me. ... Why have I done such a thing? Call me crazy.
---> '''Audience:''' YOU'RE CRAZY!
** Ben's responses to winning, losing, and tying are pretty much the same throughout.
** The "from this point on, Ben has no knowledge of the questions or answers" disclaimer given after the first break, when Ben becomes a contestant.
** Ben almost always says "I will do my best" at the start of his Best of 10 round.
** Ben reacting with faux disgust to one of the bawdy category titles.
*** Twice per Episode: Ben Stein often puts the money back in his vault via... interesting methods. Examples may include "I'm going to blow-dart my money back up on the board", pelvic thrusting it, yodeling it, and more. Essentially any verb one could perform, Ben would do that activity to put the money back.
* PrecisionFStrike: Yep, in addition to FlippingTheBird, Ben even dropped a few of these during the course of the show's run.
* PublicDomainSoundtrack: 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".
* RuleOfFunny: Many of the categories.
* RuleOfThree: In one of the early episodes, a contestant accidentally answered questions with "What is" three times. After the third instance, Ben [[RageBreakingPoint couldn't take it anymore]].
--> '''Ben:''' Okay wait a minute, this is unbelievable. This is ''unbelievable''!\\
'''Jimmy:''' (to contestant) We need a hammer, or something, to ''beat'' you with.
* RunningGag:
** As Ben appeared on stage, he was often introduced in humorous ways, such as "The man who put the T&A in SAT..." and "I swear to God he dances naked in his dressing room..."
** Many contestants answered in the form of a "[[Series/{{Jeopardy}} 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).
** At the start of the BonusRound, Ben would swear on something ridiculous that he had no knowledge of any of the questions to be asked.
** When Ben asked Jimmy to explain the BonusRound's rules, the response would be something akin to "Yes, [[Series/RedDwarf Nipple Nuts]]".
** If Ben was asked the questions second in the bonus round, Jimmy would ask an eleventh question if time had not expired. A few such examples:
-->'''Jimmy''' (''if Ben won''): Would you like to cuddle after the show?
-->'''Jimmy''' (''during a Ben win''): Are hookers deductible as "entertainment expenses"? (''To which Ben answered, "Yes, of course."''')
-->'''Jimmy''' (''if Ben lost''): How does it feel to lose $5,000?
* SmartPeopleKnowLatin: One of the categories was called "I speak Latin, ''ergo'' I am annoying."
* SoundProofBooth: Used in the Best of Ten round.
* TemptingFate: In a legendary second season episode, at the Best of 10, Jimmy wheeled out the safe with Ben's shoes on it (they played ''Strip Ben Stein of His Clothes'' in Round 2, but only one answer from the challengers to strip was provided), and asked Ben to drop his pants if he lost the final, saying HE will do it too. Cue opponent Bob becoming the first challenger in the show's history to answer all 10 questions correctly, and Ben missing one and ensuring a loss.
* ThoseTwoGuys: Ben and Jimmy played off each other quite well.
* TitleDrop: Occurred every time the show returned from commercial breaks.
* TransatlanticEquivalent: ''[[http://ukgameshows.com/ukgs/Win_Beadle%27s_Money Win Jeremy Beadle's Money]]'' aired on Creator/ChannelFive from 2 August to 22 December 1999. Appropriately, Beadle was just as NintendoHard as Stein.
* UnwinnableByDesign: 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.
** Even so, there were times that Ben didn't lose all that much money. The record lowest amount of money Ben ever lost was a mere $150.
* WaxingLyrical: At the beginning of each show, Ben recites a pop culture reference in monotone before putting $5,000 up for grabs. Song lyrics are common.
* WholesomeCrossdresser:
** As mentioned above, Ben dressed up as First Lady Barbara Bush in one episode.
** Another episode had Ben, Jimmy, and the three contestants in gender-swapped clothes. Jimmy wasn't too keen to this.
---> '''Jimmy:''' [[ADateWithRosiePalms I won't be able to masturbate for a week!]]
* WhoWantsToBeWhoWantsToBeAMillionaire: One episode was a parody of the show, complete with lifelines.
--> '''Jimmy:''' If you are too stupid to answer the questions in this round, we've got three ways to help you cheat. Number one, you can dial 1-900-ASS-PARTY; they may not have the answers, but it is a lot of fun. Number two, you can poll our audience, but they're really only good if it's a drug question. And, number three, you can ask me, but that's not usually much help either.
** Which also counted as BitingTheHandHumor- as explained above, Creator/{{Disney}}/Creator/{{ABC}} produced this show through their Buena Vista TV arm.