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If you liked School Rumble add

...then you might like Beelzebub add

Beelzebub and School Rumble are both absurd comedies with a delinquent as the protagonist. The main difference between these two anime is that Beelzebub does not feature romance as a heavy driver of plot and instead focuses on action, as the protagonist seeks to become the toughest kid at school with the help of demon powers.

If you liked Full Metal Panic? Fumoffu add

...then you might like Gakkou no Kaidan add

Ghost Stories' notorious English dub contains offensive humor and witty satire. Granted, this show's original material was not meant to serve as a vehicle for dark humor, so most of the humor derives from the writing. Still, if you want to get a taste of anime with a sense of humor emblematic of the early 2000s, this is a bastion for black comedy.