Disclaimer: I don't own Naruto, or the Akatsuki (and it's a damn shame about that too… oh the possibilities!)
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How to Amuse Yourself at Itachi's Expense!
Tell him he's ugly, then run for dear life.
Introduce him to your friends as "Weasel Boy".
List the reasons why men shouldn't wear nailpolish
Repeatedly ask him if he has a death wish because he left Sasuke alive
Tell him Orochimaru is bragging about how he "kicked Itachi's sorry ass" before leaving Akatsuki
Watch as he beats the Snake Sanin with a large club
Ask him a question. When he answers, ask him "why?"; repeat asking "why?" until he yells "SHUT UP!" at you.
After doing this, as soon as he's out of range, skip around the Akatsuki base singing "Itachi's PMSing "
When one of the other Akatsuki asks you what in the hell you're doing, tell them Itachi has PMS. When they say "Wait, do you mean to say…?" respond with a positive sounding "Hn" that they will take as a yes.
When Itachi finds out about this and tracks down the member who started the rumor that he was really a girl, that person will say that you told them. When Itachi drags that person along to track you down, point at the person while crying anime tears and say "Why are you saying that?! I only said that he was having a bad day! Itachi-oniisama, please believe me! (cue adorable, pouting, chibi face and halo)
Mentally sicker as Itachi beats the shite out of the other Akatsuki member for making you cry. (don't show amusement in your expression unless you want to be beaten to a bloody pulp because Itachi figured it out from your expression.)
Lock Itachi in a room with Tobi when he (Tobi) is high on sugar and caffeine
When Itachi unbuttons his cloak to look cool, videotape it. Put the song "I'm in Love With a Stripper" in the background and post it on YouTube; entitle the video "Itachi is a Stripper"
Using the same footage, make a new video (Itachi is a Stripper part 2) with the song "Buttons" as background music.
Show the two videos to the Akatsuki members (except Itachi); then show them to Itachi and blame the videos on Kisame
Order 500 boxes of face cream in his name and have them delivered to his bedroom
Hack into Itachi's e-mail and send a message to Leader with many, many insults; then get the hell out of there before Pein blows a fuse
Photo shop a picture of him so he looks like a woman in a bikini, then e-mail this to everyone in Akatsuki
Turn him into a chibi, then charge 19.95 for his fangirls to hug him for 5 minutes strait
Make him watch the movie "Childs Play". When he goes to bed, take one of Sasori's puppets and scare him with it when he's half asleep
On Halloween, knock him out, dress him in a weasel costume, and put him on a lawn chair in the front yard, holding a bowl of candy hearts
Force him to watch the YouTube video "Sexy Naughty Bitchy Itachi" ; watch as he destroys the computer with Amaterasu