 If you liked
Shinchou Yuusha: Kono Yuusha ga Ore Tueee Kuse ni Shinchou Sugiru
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 ...then you might like
Meikyuu Black Company
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Both of these Isekai rely on out there overall concepts that may not be every potential viewers cup of tea, yet for those looking for series that think outside of the box and have found this in one of the two may find what they're looking for in the other.
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Recommended by Yemi_Hikari
Both animes stand apart from classic isekai series with their unique sense of humor. In Cautious Hero, the humor comes from the protagonist's extremely strong will and overly cautious personality. On the other hand, in The Dungeon of Black Company, the humor stems from the protagonist's determination to become the strongest and reach the top, along with the unpredictability of his personality and his tendency to perform good or bad actions in absurd and unexpected ways throughout his journey.
Both are isekai that share a similar type of humor.
- In Cautious Hero, the MC is OP and the other characters are surprised by this.
- In Dungeon of Black Company, the MC is OP in that he is very smart, so he games the system in ways that surprises the other characters.
I found both to be very funny enjoyable.
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Recommended by sirnothing