I'd say Konan,Itachi and Nagato. Konan fought Tobi till the very end and she almost killed him hadn't he used Izanagi. She died an honorable death,fighting for her beliefs and continuing Yahiko's and Nagato's will. Nagato died god-like after reviving the dead shinobi. Itachi's death was somehow...
Itachi has amaterasu,tsukiyomi and susanoo while sasuke possesses something different than tsukiyomi maybe the power to control the flames of amaterasu. as for madara idk