First the humor, then the serious:
There may be some female 5th questers, you never know...
With so many 5th quest entries, I imagine that few, if any, will play each quest to completion. I am wondering how -est-ness can be determined in that case. But, even so, I've played a little of each quest already myself, and I can certainly tell from an early point which have high or low NES authenticity, so maybe the other categories will fall into place similarly.
Hey, how about this one:
Pun-y Human (Funniest text strings) Award.