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The 25 Funniest Comedy Central Shows of All Time

20. Win Ben Stein's Money

Air dates: July 28, 1997-January 31, 2003
Stars: Ben Stein, Jimmy Kimmel, Nancy Pimental, Sal Iacono

Pop culture enthusiasts knew Ben Stein from his droll, lifeless, though funny scenes in the 1986 flick Ferris Bueller's Day Off ("Buellller? Buellller?"), but one look at his résumé shows that he's much more professionally decorated than that. As in, he was both a speechwriter and lawyer for presidents Richard Nixon and Gerald Ford. Clearly, he's a brainy guy.

Hence Comedy Central's unconventional game show Win Ben Stein's Money, in which host Jimmy Kimmel would ask contestants trivia questions to see if they were smart enough to beat the eponymous, and proud, nerd. In reality, though, Stein never actually feared that he'd lose his own cash, since the winnings were pooled together from a prize budget, not his savings account. See, we told you he's shrewd.

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