Now, why we keep calling it Akatsuki, when we could call it Red moon?
And Itachi, weasel, for that matter???? [img]i/expressions/face-icon-small-smile.gif[/img]

And speaking of Itachi, I agree with Tenkei. He's too much entangled with Sasuke, to me is more like is there to be the excuse for Sasuke's angst than anything else.
As a character, he doesn't have a clear agenda, I mean his goal of getting Naruto is sorta weird. He is not doing it for himself, but for somebody else. No decent bad guy would be a mere henchman of an organization, much less bossed around.
Orochimaru has a clear agenda, even though I consider it a bit stupid, but he is his own man, or snake so to speak. Not only his goal is stupid, but he is stupid himself. He wasted a great deal of time with his personal revenge against the 3rd, and even lost the use of his arms in the process. Really dumb.
IMO, if he were a real smart evil guy, he'd put an act to the 3rd, saying that he was sorry, and remorseful and beg for his forgiveness in tears. Once he recovered the 3rd's trust, he could learn all the jutsus that he wanted, get Sasuke as a bonus, until finally be in a position of kill the 3rd in his sleep.
If Kabuto wasn't such an insuferable disgusting jerk, I could even respect him. Here's a guy with his own agenda and doing the smart thing. He doesn't mind being Oro's doormat, and reap the benefits from such position. The nice thing about Kabuto is that we never know when he will stab Oro in the back, and he seems smart enough to figure out the right moment, when he is strong enough and Oro vulnerable.
It may take years, but a good evil guy recognizes the value of patience as a virtue.
Still, the downfall of Kabuto may be his need for a personal revenge against Konoha.Which obviosly will impair his reasoning.
Gaara had his own agenda. To kill whatever living creature that crossed his path. He recognized it as the purpose of his existence and therefore, was happy with himself. He's a perfect evil man, if we consider evil as the supreme selfishness. He wasn't entagled in personal vendettas, his goal wasn't make other people suffer, but simply to kill them. He didn't need to kill anybody in particular, so he didn't go through a great deal of trouble to kill *a* specific person. He said he'd kill Shikamaru and Naruto, but he could wait for the best opportunity to do it. There was no hurry. Again, for the good evil guy patience will always be a virtue.
Except for the old Gaara, and possibly Kabuto, the other two have too many personal problems preventing them from being decent evil-doers.