 If you liked
Sakigake!! Cromartie Koukou
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 ...then you might like
Gokushufudou
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The styles for these Anime is rough around the edges, which helps to emphasize the fact both series deal with societal rejects. One takes place in high school while the other ends up involving adults, yet there is major levels of crazy going on with the plot.
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Recommended by Yemi_Hikari
Both are shows about "the underbelly" of society trying to go about everyday lives. Both are primarily about Delinquents and (ex)Yakuza getting up to every day activities in ridiculous ways. They share similar gag style humor, highly based on timing and the characters acting in ways that those around them are shocked by. It also turns the stereotypes of these types of characters upside down, showing that they are also caring people. If you enjoy the humor of one, you are sure to laugh at the other.