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Orochimaru
Killed 28 times
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Tooth Fairy
Killed 28 times
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From Wikipedia:
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Orochimaru (大蛇丸), featured in the Japanese folktale Jiraiya Goketsu Monogatari, is the arch-enemy of the ninja Jiraiya. He was once named Yashagorō (夜叉五郎) and was one of Jiraiya's followers, but he was overtaken by serpent magic. Having changed his name to "Orochimaru", he gained the ability to turn himself into a giant serpent. He attacked Jiraiya and his wife Tsunade and defeated them with his venom (only for another follower to save the couple's lives afterwards). "Orochi" is the name of a giant eight-headed snake in Japanese mythology. The kanji (大蛇, usually pronounced daija) literally mean "giant snake" or "serpent". |
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The tooth fairy is a fairy which gives a child a gift in exchange for a tooth that has come out. A child typically leaves the tooth under their pillow for the fairy to take while they sleep. The tooth fairy then adds the tooth to a special part of her all-white tooth castle in the sky. The myth in this form is practiced in the US, Ireland, Germany, Italy, South Africa, Australia, Canada, New Zealand, Portugal and the UK.
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Sasuke vs Orochimaru, 
