Hisoka's smile from Hunter x Hunter is sinister and unsettling
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The Yandere Queen, Gasai Yuno's smile from Mirai Nikki is psychotic
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Shinra Kusakabe's smile from Fire Force is creepy as hell
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Tomura Shigaraki's from My Hero Academia has a legit Creepy Villainous Smile
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Doflamingo's from One Piece grin goes over the moon whenever his plans go as planned
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Sawako Kuronuma's smile from From Met To You is scary resembling a ghost from 'The Rings'
Image: Google