Achievements: Graduated from the Ninja academy at age 7 with top grades, mastered the Sharingan at age 8, became a Chuunin at age 10, Anbu leader at age 12, wiped out his entire clan and promoted to S-class missing nin at age 13.

The Deal with him: Top member of secret society Akatsuki, who even Orochimaru admits is stronger than himself, Itachi is shrouded with mystery. He killed his whole family with the reason that it was to measure his strength. He left his little brother alive after screwing up his mind. Although it seemed that Itachi spared his brother so he could become stronger and thus a worthy opponent someday, we believe that somewhere deep in his very disturbed heart, he loves Sasuke in his own very weird fashion.

From someone who killed his whole family, Itachi is surprisingly unconfrontational and unbloodthirsty unlike how one would expect him to be. There were many incidents when he could have easily killed an adversary but instead left them heavily wounded and avoided as many fights as he could. Itachi has issues and it would be delightful when we finally find out why.