Itachi.
Orochimaru's was a bit... evil mad scientist and limited in terms of making me empathise with him. I didn't and couldn't give a f*ck about him. At all.
Gaara. Actually, with more consideration I think I'd rank him quite high. Easy to empathise with, largely due to Naruto's ability to do so. And the soundtrack, that helps - and his epic speech at the 4th Shinobi War.
The confrontation with his father, revelation about his mother - very satisfying. Liked it.
Obito. I empathised with Kakashi - not Obito. Didn't like him before he "died", or during and his mad rants about Rin made me want to bash his head in.
Madara. Meh. Thanks to Hashirama, I care a bit more but I'm not invested in him as I am with others.
Shikamaru. Good character, good development. I like him, but I don't love him. He's a cool guy, but it kind of stops there for me.
