Lists of things that the Akatsuki would never do...

Itachi would never...

run up to his brother Sasuke and hug him.
become a drag queen
eat a live squid
tell Kisame how much he he appreciates their friendship
make a porn movie and post it on the internet
bleach his Akatsuki cloak and then dye it pink
use under-eye coverup makeup to cover those lines beneath his eyes
dress up in a weasel costume and stalk people
answer the phone saying, "weasel weasel weasel..."
pretend to be the tooth fairy for a small child
walk around an anime convention carrying a sign that says, "Need help restoring clan."
walk up to Sakura, kiss her on the lips and run off squealing in delight
carry a pink parasol with him everywhere to protect his skin from sun damage
sleep with a teddy bear
tell Sasuke that he's scared of the dark and ask to borrow a flashlight
pose and give a motto when he and Kisame appear
demand his money back from a vending machine, and then destroy it with the Ameterasu when it doesn't return it
make a list like this and post it online
collect swimsuit photos of Tsunade
make out with a fangirl
keep a pair of Madagascar hissing cockroaches as pets
adopt a stray kitten from a shelter and lovingly care for it
pour super glue on a toilet seat and wait for someone to get stuck, then steal their wallet
ask if Kisame has a sister- if he says yes, then ask if they can go out together, since he loves the blue skin look
force-feed Kisame shark's fin soup

become a vegan
keep kosher
get married
write a hentai manga about plants
wear a furisode
serenade someone outside their window with sweet love songs
make an anime music video
hug someone with the jaws of his plant
make suggestive prank phone calls to Temari
go swimming in frigid Alaskan waters
do a little dance in the middle of a shopping mall
join an online Naruto fanclub
say "goodbye, cruel world" and spray himself with weed killer
walk around without clothes, since his plant covers him up [it wouldn't really be indecent- just weird]
grow a ton of pink flowers on his plant every spring
get drunk on fertilizer
stage a hostile takeover of a garden store

give up art and become a pro wrestler
elope with a random fangirl
buy a coloring book and start coloring it, calling it art
become a pacifist
cut off all of his hair and dye the stubble lime green
grow a thick mustache, wear glasses and start talking with a European accent in an effort to appear smarter...
...then change his last name to "Einstein" to complete his new image
wear spandex [...actually, he might, but the idea is too scary to consider...]
collect action figures
open a furniture store
write a commentary on Tolstoy's book War and Peace
participate in a pie-eating contest
illustrate yaoi doujinshi featuring Itachi