 If you liked
Princess Princess
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 ...then you might like
Marginal Prince: Gekkeiju no Ouji-tachi
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Both series follow a clique of students and their silly adventures at an all boys school. Family troubles balance the mood and both have their own unique entertaining quirk: compulsory crossdressing in Princess Princess, episodic nonsequitur singing in Marginal Prince.
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Recommended by lithiumflower