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For me, it would probably have to be between Itachi and...Madara. I have always liked the Uchiha characters in the series (Except for Sasuke...damn emo complex).

However, I do think that some of their individual talents should be taken into account. Itachi, for starters, was a professional in every aspect of combat, including Taijutsu, which is something Genjutsu masters such as himself don't normally engage in. Not only that, but as it has been stated multiple times in this thread, Itachi attained ranks at very young ages. Skill like his had never been seen in the Leaf Village before, and I daresay it shall be for a while.

Madara, on the other hand, has been scheming and plotting for YEARS. His skills obviously rival that of any ninja, as he is able to manipulate the Kyuubi to a degree, as well as put the roots into what would later become Akatsuki. I have to say though, his ability to use Izanagi without consequence is undeniably cheap. Another trait that could undermine him was the fact that Konan, a ninja that hadn't REALLY had a prominent role in the Narutoverse, was able to almost kill him. In fact, if he didn't have Izanagi, he would be dead in the series already.

I saw mention of the Third Hokage in this thread. That is one I'll have to argue. In the Sand/Sound Invasion of Konoha, Sarutobi was defeated by Orochimaru; it seems like everybody and their mother could easily kill Orochimaru now. XD

JIRAIYA AND MADARA ALL THE F***** WAY

Ide have to say Orochimaru, He had many plans, all of which he seemed to put Alot of detail in, some failed, some went off without a hitch. He I feel is the only actual villian to date. (sorry thats off topic lol) He is the only person to my knowledge to face 4 tailed naruto, and just laugh at it, even after getting smacked halfway across the forrest. and something tells me this whole sasuke beating him and the curse seal being gone is part of a gaint plan orochimaru has. This man is/was a thinker and i dont think he would over look something like this hapening.