Well there were a number of things that made parts of the interview weird... and really, weird is the best word to describe it. I don't think it was a bad interview. It was a pretty good one.
For example, I already mentioned the whole "fair/unfair" thing... Then there was the issue of "justice" and the idea that "there is no way to measure whether or not someone deserves something." Also, there was the whole reading and running will make you happy thing...
I agree to an extent with his view of the current educational system. While I think that having a firm understanding of something like history (including dates, people, locations) is vital, I agree that there often isn't the proper emphasis on the significance of the events, but rather just an exercise in remembering the dates, people and locations.
In general, he seemed to make a lot of concepts that should have been straight forward, somewhat convoluted, though I think that was more the interviewer's fault than his. For example, Will mentioned that the way in which he picked a few of his film projects was that he observed some of the patterns in the film industry. He considered which were the more successful films, and chose to do films like those. Simple concept. But then the interviewer asked him how he learned to do that. I'm thinking... "Well, common sense." But it becomes a thing, when it could have stopped at his initial answer.