hmmmmmm tuff choice... id say my top 5 favorite characters are
Itachi, shisui, Obito, Kakashi, Sasuke, and naruto... wait that's 6 but those dudes have a few sad things in common... THEY ALL HAD TO PUT UP WITH ALL THE LEAF VILLAGES SHIT, THEY ALL BECAME OUTCASTS FOR SOME TIME, AND THE LAST THING IS THERE'S A LOOP WITH ALL OF THEM... I will now explain it... so basically it started with Obito ofc cuz Obito was lied to by Madara, then saw the girl he loved die by his BSF which was Kakashi and that also destroyed Kakashi cuz rin purposely went in front of Kakashi's attack so that she wouldn't be used for her tailed beast, which then Obito provoked/ helped Itachi to kill off his clan and before that, shisui kinda topped off Itachi's rage and anger by saying ight ima bout to head into this bottomless pit of agua, which also fueled sasuke's rage cuz Itachi had to do what he had to do *sniff, then Obito used the nine tails to try and destroy the village (props to Minato and kushina), who then sealed the 9 tails into naruto making naruto the feared demon boy of the leaf village making it so that fate would bring Naruto and Sasuke together and also making it so Sasuke leaves the village to get more power and kill Itachi. and boom that all I'm gonna say cuz I'm tired of typing, if you want more reasoning dm me average.