 If you liked
Black★Rock Shooter (TV)
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 ...then you might like
Mekakucity Actors
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They're both based on Vocaloid songs, but Black Rock Shooter was based only one Vocaloid song, Black Rock Shooter, and Mekakucity Actors was based on the Vocaloid song series, Kagerou Project
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Recommended by SayoKimetsu
Both were based around notable vocaloid hatsune miku especially projects and both can also be pretty edgy and trippy and share a ya cast too.
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Recommended by Disapeared_Ghost
While not similar at all, both series are based on Vocaloid songs (Black Rock Shooter and the Kagerou Project)
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Recommended by evilturkey5