Stein always had a co-host to exchange jokes with and to ask some of the questions in the game. Jimmy Kimmel was the co-host for the first three years of the show's run, but he left the show in 2000 (even though he made occasional guest appearances after that). Nancy Pimental replaced Kimmel and co-hosted the show through 2001. Sal Iacono, who took over the role in 2002, was the show's last co-host.
Once a player chose a category, Stein asked a question that was worth a value between $50 and $150, depending on the level of difficulty. If a player answered that question correctly, the value of the question was subtracted from Stein's bank and added to the contestant's score. Stein then asked that contestant a follow-up question from the same category for an additional $50; any of the opponents could answer that question if the contestant answered it incorrectly. (If nobody answered the original question correctly, Stein asked a $50 toss-up question that any of the three contestants could answer.) A new category replaced the old one after both questions were asked, and whoever won the previous question got to choose the next category.
At the end of the first round the contestant with the lowest score was eliminated from the game and that player's money was put back into Stein's bank.
A running gag on the show was performed whenever a contestant answered in the form of a question, like they do on Jeopardy: that player was forced to wear a dunce cap for the rest of the round.
The second round also contained five categories, but the questions in that round were worth anywhere between $200 and $500 of Stein's money if a contestant answered them correctly. (If Stein answered a question correctly, the bank total did not change.) Follow-up questions were not asked in this round.
The contestant with the lowest score at the end of the second round was eliminated from the game, with his or her winnings going back into Stein's bank.Rules of the game
First round
The game began with three contestants, five categories that were read by the co-host, and $5,000 in Stein's bank. Second round
Stein competed against the two remaining contestants in this round, answering questions from the eliminated player's podium. The co-host -- who always gave a disclaimer stating that Stein had no advance knowledge of the questions from that point forward -- asked the questions in this round.