 If you liked
Sayonara Zetsubou Sensei
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 ...then you might like
Aoi Bungaku Series
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No rec for these two series yet? Zetsuboushita!
Itoshiki-sensei and Yozo Oba are based upon the main character of No Longer Human, Osamu Dazai's novel. In fact, they share the same characteristics: an handsome, kimono-wearing young man, popular with women, and (attempting to be) suicidal because society left him hopelessly in despair.
Both anime revolve around more or less the same matters of despair, death, and being human, although is opposite ways.
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Recommended by RenaPsychoKiller