 If you liked
Prison School
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 ...then you might like
Back Street Girls: Gokudolls
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Main characters are stuck in a situation (a school prison; men being forced to act like idols) where they cannot decide their fate, and get involved in a spiral of disgusting situations which always end up in dark humor.
Harsh, dark humor. "Explicit" content. Sex jokes.
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Recommended by Z_Tetriminos
These anime anime are completely different when reading they're synopsis, but when you watch them they are almost one and the same. They are both absurd, and have over the top reactions.
If you like weird, ''WTF'' comedy, you'll have a blast watching these!
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Recommended by AlexPlayer
Dumb toilet humor? check.
A bunch of horny guys forced into an unnatural and uncomfortable situation? check.
Villainous perverted mustache man? check.
These two shows have an unique appeal, and a very peculiar sense of humor.
If you liked the over-the-top inappropriate gags of prison school, you'll enjoy BSG's just as much.
Both are very comical in nature and include NSFW humor
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Recommended by Lavander_why
Both these anime have a lot of adult humor and good pacing
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Recommended by Bubbles1512
both are funny in a WTF, dark adult humor way.
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Recommended by indoorparkour
they are both funny and stupid at the same time.
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Recommended by gioelernesto