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  2. In the second round, questions are worth $800–$2,000 in increments of $400. In both episodes, the winners attempt to defeat Stein for the entire $25,000. The first "Ben Stein's Cup" is co-hosted by Jimmy Kimmel, with the second co-hosted by Nancy Pimental.

    • Al Burton, Donnie Brainard, Byron Glore, Andrew J. Golder
    • Game show
    • Dennis Rosenblatt
  3. This is no ordinary episode of Win Ben Stein's Money. This is the second time Ben brought champions together to play for 4x the stakes in the maingame and a ...

    • Jul 22, 2010
    • 68.5K
    • Hondo20132
  4. Round 2 and the Best of 10 are seen in this high-staked version of the game! Who will win, and will the big money be won? Watch and find out, of course (that...

    • Jul 22, 2010
    • 63.7K
    • Hondo20132
  5. Episode aired 2000. TV-PG. YOUR RATING. Rate. Comedy Game-Show. The second episode of the Ben Stein's Cup; the grand prize is $25,000 of Ben's money. Stars. Nancy M. Pimental. Ben Stein.

    • Comedy, Game-Show
    • 30
    • 2000
    • Nancy M. Pimental, Ben Stein
  6. On two occasions in Season 4, three of the show's best contestants (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).

  7. Win Ben Stein's Money is an American television game show created by Al Burton and Donnie Brainard that aired first-run episodes from July 28, 1997, to January 31, 2003, on Comedy Central. The show features three contestants who compete to answer general knowledge questions to win the grand prize of $5,000 from the show's host, Ben Stein. In the second half of each episode, Stein participates ...

  8. Feb 25, 2023 · In both episodes, the winners attempted to defeat Stein for the entire $25,000, and the first "Ben Stein's Cup" was co-hosted by Jimmy Kimmel, while the second was co-hosted by Nancy Pimental. In conclusion, "Win Ben Stein's Money" was a game show that had a unique format and was a hit with audiences during its run.

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