I spoke today to a friend of mine who was involved in the now-cancelled game show, Win Ben Stein's Money. So why does he think it was cancelled?
Three reasons. One was that it was getting repetitive. No matter how much we tried to wring variations on the format, every episode felt like you'd seen it before. The second reason was that we never found a sidekick who provided the chemistry that Ben had with Jimmy Kimmel. And the third reason and, for me, the biggest one was that Ben was winning too much. People tuned in to see the wealthy, snotty guy get topped by the guy off the street and that wasn't happening often enough.
Then my friend adds a fourth reason: "Actually, the main reason Comedy Central bailed was that they simply figure they've got enough of them. If the show has any ongoing rerun value, it won't matter if they more than they presently have. They'd rather put their 'new programming' money into building a library of something else."