Win Ben Stein’s Money, a Comedy Central game show airing from 1997 to 2003, offered a unique twist on the quiz show format. Instead of just competing against other contestants, participants had the chance to challenge the erudite Ben Stein himself for a share of the prize money. This article delves into the format and highlights of this quirky and entertaining show.
How to Win Ben Stein’s Money: The Game Format
The game unfolded in three rounds, each designed to test contestants’ knowledge and strategic thinking. The ultimate goal: to outsmart Ben Stein and win the coveted $5,000 grand prize.
Round One: General Knowledge Face-Off
Three contestants initially faced off in a general knowledge round. Five categories, each concealing questions with values ranging from $50 to $150, were presented. Ben Stein himself posed the questions. A correct answer deducted the question’s value from the total prize pot, with a bonus $50 awarded for answering a supplementary question correctly. All questions were displayed on a screen, adding a visual element to the game. 
Contestants answering questions in Round 1
Round Two: Ben Stein Joins the Fray
The lowest-scoring contestant from Round One was eliminated, with their accumulated winnings returned to the prize pool. Ben Stein then took the eliminated contestant’s place, leveling the playing field. Jimmy Kimmel, the show’s co-host, took over the questioning duties, presenting questions worth between $200 and $500. Crucially, Ben Stein had no prior knowledge of the questions. If he answered correctly, he didn’t win any money; instead, he prevented the remaining contestants from depleting the prize fund. There were no supplementary questions in this round. The eliminated contestant’s money was again added back to the pot. 
Ben Stein participating in Round 2
Round Three: The Final Showdown
The remaining contestant had the opportunity to win the full $5,000 by facing Ben Stein in a head-to-head final round. They could choose to answer questions first or second. Both entered separate isolation booths, ensuring a fair contest. The stark contrast between the contestant’s basic booth and Ben’s luxurious one added a humorous touch. Each was asked ten challenging general knowledge questions within a 60-second time limit. Winning against Ben Stein was a rare feat. 
Final round isolation booths
The final outcome determined the prize. A contestant victory meant winning the full $5,000. A tie resulted in the contestant winning their accumulated earnings plus a $1,000 bonus. If Ben Stein prevailed, the contestant kept their existing winnings, while Ben maintained his intellectual reputation. Special episodes offered previous winners the chance to compete for a $25,000 prize.
Win Ben Stein’s Money: A Lasting Legacy
Win Ben Stein’s Money, with over 600 episodes produced, garnered critical acclaim and numerous awards. Its unique format, challenging questions, and the comedic interplay between Ben Stein and Jimmy Kimmel made it a standout in the game show landscape. The show’s enduring popularity speaks to its engaging and quirky nature.
