Itachi :
5) Massacring all of the Uchiha (for the sake of the village).
4) How he was introduced when returning to the Hidden Leaf after the Third died by Asuma, Kurenai, Kakashi, and later Gai.
3) When Sasuke whipped out the "Karin" and Itachi was all like "Susanoo, mother****er"
2) When Tobi is telling Sasuke about his brother and says, "Yada yada yada... He killed his entire clan, left the village as a criminal, making you hate him, and Itachi still died with a smile on his face". Or something like that.
Number One Itachi Moment) That impressive ****ing music that goes on in the anime when Sasuke stabs Itachi and the clone points two fingers up and to the side, signaling Sasuke to look at the real Itachi.