Re. Matthew Miller's interest in "insane" midrashim, here's one (I don't have the citation in front of me):
The 600,000 letters of the Torah correspond to the 600,000 members of B'nei Yisrael at Sinai. Two problems with this: The Torah only has slightly more than 300,000 letters, and the tally at Sinai does not include women, children, and the elderly. Task: Make sense of this midrash.