 If you liked
Sayonara Zetsubou Sensei
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 ...then you might like
Vlad Love
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Vlad Love and and Sayonara Zetsubou Sensei both are set in a school, but lack a school themed plot. Rather, an eccentric teacher and a group of equally wacky students are used to discuss sophisticated themes and take ensemble roles in random settings. SZS covers mainly social commentary on idiosyncrasies of Japanese society, while VL mainly deals with the arts and cultural themes (movies in particular). Both use countless references to to their sophisticated non-anime subject matters casually. This often requires side-reading and a rich education to understand all the gags. Both shows have an experimental animation style, episodic structure, and random gag based
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