Win Ben Stein's Money is a game show that requires some brains (unlike Wheel of Fortune) but is funny and doesn't take itself as seriously as Jeopardy. The show is hosted by Ben Stein, who is probably most famous for his appearances as a teacher in "The Wonder Years" and "Ferris Bueller's Day Off", along with Jimmy Kimmel as the smart-ass side-kick.
There is a lot of shtick, and good interplay between Stein and Kimmel that gives the show both humor and likeability. Kimmel is funny and rude, but occasionally crosses the line to gross or mean. Special theme episodes are occasionally shown, such as a recent cross-dressing episode. Another fun bit, is that if a contestant answers in the form of question, ala Jeopardy, they are forced to wear a dunce cap.
The premise of the show is that Stein has put up $5,000, which he will try to keep the contestants from winning. The exact financial details might vary somewhat - fine print at the end of the show hints at this. Stein competes against the contestants, usually successfully.
The show starts with 3 contestants, who choose from five categories, with various joke/scatological titles. Questions are assigned a dollar value for correct answers, and in the first round have a $50 follow-up. At the end of the first round, the contestant with the lowest winnings is dropped, and replaced by Ben Stein. At the end of the second round, the contestant with the highest winnings is selected to go on to the "Best of Ten Test of Knowledge", a one-on-one contest directly against Stein. The constestant and Stein are locked in isolation booths (one of the jokes is that the contestant's booth has a bare lightbulb, steel stool, and cracked plaster, while Stein sits in a booth with paneling, and an overstuffed chair). The contestant and Stein are given the same ten questions, and if the contestant beats Stein is given all $5000 dollars put up by Stein.
The show airs on Comedy Central, Monday-Friday, twice in the evening.
