Anime Villain!Male Reader x Overlord vote. As for their nations, I'll use one of Skyrim's Cities.
1) Findorr Calius (Falkreath)
2) Douma (Winterhold)
3) Jackal (Morthal)
4) Naraku (Whiterun)
5) Halloween (Solitude)
6) Deidara (Riften)
7) Crocodile (Markarth)
8) Yevgraf (Dawnstar)
9) PoH (Windhelm)