| Host | |
| Ben Stein | |
| Co-Hosts/Announcers | |
| Jimmy Kimmel (1997–2000) Nancy Pimental (2000–2001) Sal Iacono (2002–2003) | |
| Broadcast | |
    | |
| Packagers | |
| Valleycrest Productions Comedy Central | |
| Distributor | |
| Buena Vista Television | |
Win Ben Stein's Money featured three contestants competing in a Q & A styled game against each other and eventually Ben Stein in an attempt to win $5,000 of his money.
Gameplay
The First Two Rounds
In the first two rounds, the contestants involved faced a game board of five categories inside five picture frames (in the first season they appeared as cards, but in Season 2 and beyond, the cards were replaced with monitors). Each category was a pun hinting at the question's content, similar to Pyramid or the JD Roberto era of Shop 'Til You Drop.
A contestant in control picked a category, and then a dollar amount was revealed behind it after which a question was read (the questions were just heard in the first season, but in the rest of the series, the questions were also seen on the monitor the chosen category appeared after the amount was revealed). The first contestant to ring in with the correct answer scored the hidden dollar amount; plus, that amount was taken away from Ben's total. After each question, a new category replaced the one chosen.
The rounds were played in an unmentioned time limit, and time was called when a cuckoo clock sounded. The player with the lowest amount at the end of each round was eliminated from the game, and all the money he/she took was returned to Ben and added back to his total. Also, if at any point a player answered in the form of a question (as on Jeopardy!), Stein, in mock anger, would place a dunce cap onto the offending player's head and he/she was forced to wear it for the rest of the round.
Round 1
In Round 1, the three contestants faced-off against each other, and Ben read all the questions. The questions were worth either $50, $100, or $150. Each time a contestant answered the first question correctly for the amount showing, that contestant had a chance to answer a $50 follow-up question; should all three contestants miss the first question, the follow-up became a toss-up for all three contestants.
If there was a tie for second place after this round, a tiebreaker question was asked, and if the first contestant to ring in with the correct answer would move on; however, if they answered the question incorrectly, the opponent would move on.
Round 2
In Round 2, the survivors of the first round played not only against each other, but against Ben as well as he became a common contestant trying to defend his money; because of that, the co-host read all the questions, with the disclaimer that "from this point on, Ben has no advance knowledge of any of the questions to be asked." or that "This is the part of the show where we remind everyone that Ben does not get the answers to the questions ahead of time."
Ben would always stand at the third podium for the second round. If a contestant got eliminated from the third podium, Ben simply would take over that spot. If a contestant got eliminated from the second podium, one contestant moved one spot closer to make way for Ben entering the third podium. And if a contestant got eliminated from the first podium, both contestants would move one spot over or (later in the run) the contestant from the third podium would move to the first podium to make way for Ben entering the third podium.
This time the question values increased to the range of $200-$500 in $100 increments to the contestants should they get them right; if Ben got a question right each time, his remaining total stayed the same. To accommodate this, the scoring display on his podium showed a dollar sign. Ben made the first selection in this round, and there were no follow-up questions this round.
The contestant with the most money at the end of this round got to keep it and went on to take on Ben Stein for the rest of his money. If there was a tie, a tiebreaker question was asked (without Stein answering). the first contestant to ring-in with the correct answer would move on to the bonus round; however, if the contestant answered the question incorrectly, the opponent automatically went to the bonus round.
Bonus Round: Best of 10 Test of Knowledge
The bonus round was called the Best of 10 Test of Knowledge, because both the winning contestant and Ben were both asked the same ten questions, but they played individually/one at a time. To start, the winning player had a choice to go first or second, then they sat in their own isolation booths (the winning contestant sat in a dirty plain wrap booth with a hardwood stool and a bare hanging light bulb, while Ben sat in a beautifully decorated one with a leather-wing back chair and other lavish furnishings). Whoever played second wore headphones so they could not hear the other's answers.
Each player had 60 seconds (one minute) to answer as many of those ten questions as they could, and the player who answered the most out of ten won. Missed or passed questions could not be returned to, but the co-host went over any and all of them after the first player finished. If Ben won, then the contestant took home just the money he/she won from the game; if both players were tied, the winning contestant won a $1,000 bonus in addition to the main game cash; and finally, if the winning contestant managed to beat Ben Stein and win, he/she won all $5,000 of Ben Stein's money (his/her main game score was augmented to the grand prize amount).
"Ben Stein's Cup" episode
At the end of the fourth season, three of the best contestants of the season (who had already won $5,000) returned for a special "Ben Stein's Cup" episode, for a chance to win five times the amount ($25,000). The question values in the main game were multiplied by four; so in Round 1, the question values were $200, $400, and $600; with follow-up questions worth $200, and in Round 2, the questions were worth $800-$2,000 in increments of $400. The winner attempted to beat Ben Stein for the entire $25,000.
In a previous "Ben Stein's Cup" episode in Season 2, three contestants who already won $5,000 received a chance to win another $5,000. Question values in the first two rounds were the same as always.
Music
Ben Stein's Intro – "Wachet auf, ruft uns die Stimme" by Johann Sebastian Bach
Open/2nd Commercial Outro/Win – "Ode to Joy" by Ludwig Von Beethoven
Close – "Ride of the Valkyries" by Richard Wagner (this was also played in the contestants' headphones in the isolation booth to prevent them from hearing the other contestant's answers)
1st Commercial Intro – "Water Music" by George Frederic Handel
1st Commercial Outro – "Spring" by Antonio Vivaldi
2nd Commercial Intro – "Eine Kleine Nachtmusik" by Wolfgang Amadeus Mozart
3rd Commercial Intro – "Trepak" by Pyotr Ilych Tchaikovsky
3rd Commercial Outro – "Night on Bald Mountain" by Modest Petrovich Mussorgsky
Studio
Hollywood Center Studios, Los Angeles, CA
Rating
Trivia
- At one time during the third season, Ben & Jimmy traded jobs for one episode up to the Best of 10 Test of Knowledge.
- A second season episode was one of the most talked about, for on that show, Ben was forced to strip. At first during the second round, Ben took off his shoes, but the Best of 10 Test of Knowledge was where the unthinkable happened; for when the winning contestant (whose name is Bob) won that round, Ben was forced to take off his pants (except he did it briefly). Upon Ben's brief stripping, Jimmy completely took his pants off, and then the winning contestant did a brief stripping himself. Also what makes this show memorable was that Bob was the first contestant to get all ten questions right (Ben answered nine).
- Ben & Jimmy (as well as the contestants) would participate in special themed episodes, including a flashback to the sixties.
- From 1997-1999, the Ben Stein statue from the top of the ceiling is shown in between the Best of 10 Test of Knowledge, and during the closing credits. It was replaced with a oval projection screen beginning in the 2000 Season until the end of the run.
- One episode from 1997 had Jackie and Sammi Forrest of Fun House fame appear as the "Ben Stein Cheerleaders"
Merchandise
WBSM Interactive
GSN's website once had a live interactive game where you can play along with the show.
International Versions
An unsuccessful Australian version called Win Roy & H.G.'s Money hosted by "Rampaging" Roy Slaven (John Doyle) and H.G. Nelson (Greig Pickhaver) ran on the Seven Network for a brief period in 2000. The grand prize for this version was also $5,000.
An equally unsuccessful British version called Win Beadle's Money hosted by the late Jeremy Beadle along with Richard Morton as co-host ran on Channel 5 for five months from 2 August (August 2) until 22 December (December 22) 1999. The grand prize for this version was a thousand pounds.
Additional Pages
Win Ben Stein's Money/Quotes & Catchphrases
Win Ben Stein's Money/Gallery
Win Ben Stein's Money/Video Gallery
Links
Win Ben Stein's Money @ Comedy Central.com (via Internet Archive)
Win Ben Stein's Money @ futility.com (via Internet Archive)
Episode Guide
Win Ben Stein's Money @ Salute to Game Shows
How one contestant managed to Win Ben Stein's Money