Nozomu Itoshiki is the extremely pessimistic school teacher in the series "Sayonara Zetsubou Sensei." Along with this extremely depressed teacher are his wide array of students just as crazy. A stalker, shut-in, OCD perfectionist, etc.
Each story revolves around a general topic of every-day life that we find normal/positive, and uses satiric humor to show arrays of negative, yet hilarious sides of the subject.
(Note: hard to find a good ref pic, but he DOES wear tabi & sandals)