10 Ways to Annoy Uchiha Itachi
Go ask him why he didn't kill Sasuke… when he answers then ask him why he didn't kill Tobi then repeat with Sasuke and so on…
Ask Kisame to play 'Billy the Theme Park Shark' for 72 hours straight.
When he's sleeping use Sasuke's hair gel to make his hair just like Sasuke's.
Dye the clouds on his Akatsuki cloak pink.
When he finally goes blind, offer to guide him. Then, make him crash into everything in sight.
Remind him that it's HIS fault that his brother is an Emo-phycopath.
Start calling him 'weasel' repeatedly. When he finally answers, say you forgot what you were going to say. Repeat several times. Then finally say "OH I REMEMBER NOW! HIII ITACHI:D"
Tell him that Pein has something important to tell him then when he goes to see paint his room pink (to match his cloak, of course) and write Tobi Was Here all over the walls.
Mock him forever with the fact that he missed ONE Uchiha.
Ask him if he wants Sasuke to kill him. (Why else would he leave him alive?)