The Great American Bore-off:

This has been a pet project of mine for a while. Basically, it would involve certain particularly boring administrators at the U of C competing to see who is in fact the most boring. Isn't this something you've always wondered about? There were a couple of logistical problems though, that Will and I tried to iron out last night.

• First, how does one get the boring administrators to come? The ones we consider the most boring don't appear to know that they are boring, and no one really wants to be the one to inform a dean that he is boring. We decided that we should invite all members of the administration, even the non-boring ones, and tell them it's a benefit for ADD. Since not that many would actually come, it could work.
  
• Then, how does one judge boring? It's a purely subjective judgment, and if we tried to judge it as people judge gymnastics, by watching and assigning a numerical score, all the judges would fall asleep. So we need Boring Stadium! It would be a big room with corners for each contestant. In the middle, one would be able to hear all the contestants; at each end, one would only be able to hear one. The person at the end of the night who has had the lowest average attendance in his corner would be judged the most boring.
  
• Third, how would we get people to come? Free alcohol, and lots of it.
  
• Fourth, how would we make money off of this? Gambling. As long as we set the odds right, we can't really lose. And wouldn't you bet on this?