Announcer - Jimmy Kimmel
As stated above, Jimmy Kimmel is Ben Stein's announcer, as well as his sidekick. During the first round, Jimmy sits on the sidelines. But he doesn't just sit idle as the game goes on. Before they start the game, Jimmy is the one who introduces the contestants. He tells who they are, and what they do. And during the first round, he announces the names of the categories as they are revealed.
During the second round, Jimmy takes over as the host as Ben becomes a common contestant to defend his money (stay tuned, you might learn something). He also still announces the names of the categories.
Finally, during the Best of Ten, Jimmy is the one who asks Ben and the contestant the ten questions. But it seems that Jimmy is not allowed IN the booth at all, even if he's hosting. When he and Ben changed places on June 16, Ben determined that the isolation booth was too scary for Jimmy, and that he would go into the isolation booth for him.
Starting in the middle of the fourth season, Jimmy Kimmel will be leaving Win Ben Stein's Money in order to concentrate on The Man Show. Replacing him will be Nancy Pimental. You can see what she looks like in the picture below...
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