Everybody drinks once whenever ... KenJen's answer ends with a stylistic flourish, like last night's, "What are the munchies, man?" in response to a clue about an 8-letter word for "hunger pangs."
The game is padded with generic rules that could be used when there is any strong champion, and the article is padded with material about great drinking games of the past. "Hi, Bob" was great because it was based on a neat observation about the show. Drink when KenJen gets one wrong is an embarrassing failure to be specific. Come on! I want some standards in my drinking games! Here's my drinking game: drink when someone announces a drinking game rule that isn't funny!
Maybe the problem is that Ken Jennings really isn't very interesting. And the show is less interesting than normal when Final Jeopardy presents no risk and no occasion for strategic betting. The only surprise is how much KenJen wins by. (An obvious missed opportunity in the Slate drinking game: there should have been a rule to drink when Ken bets just enough on Final Jeopardy to equal but not exceed the one-day record.)
On Final Jeopardy with KenJen, the people out of contention just seem like mere shells of a man/woman. What about that guy yesterday--you know, the guy that looked like Al Gore--just writing "What is ....?" when the question required the name of a country in Africa? At least name some country in Africa! The only possible thing you could lose there is your last shred of dignity if you were somehow to fail to name a country in Africa! But you did fail to ... ah ... enough already. That man was boring. And the woman was scarcely alive!
Conclusion: KenJen is making the show boring, but way more people are tuning in because of him than would watch on an ordinary day, where the contest would be more exciting. Viewers are dully observing the dollar total advance and sticking around because they want to be watching when some day KenJen falls. The percentage of viewers hoping to see him defeated probably increases each day.