Aizen vs Madara (Bleach vs Naruto)
Aizen vs Madara (Bleach vs Naruto)
Which versions? There's a surprising amount of variety here to choose from.
That people don't presume (and state their presumption of) the prime version (or at least the most current viable version) of a character is being used when a specific variant isn't mentioned by the OP is something I've always found rather odd.
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With other characters I wouldn't really feel the need to ask.
Madara and Aizen both spend a significant amount of their time of their careers being amped by outside sources (The Jyuubi and the Hougyoku respectively). "Aizen in his prime" to me would be Aizen with just his own abilities at the top of his game rather than actively amped by his merger with the Hougyoku but I don't know if OP means that.
Also, there's the added caveat with Madara aside from external powerups, he also spends a large chunk of the story as an eternally regenerating zombie which is a very different kettle of fish to Madara as he was at the top of his game during his natural life.
If we're not being pedantic then I'm guessing it's Aizen after he's gotten out of the mightiest chair this side of Critical Role against Madara after becoming the ten tails jinchuuriki but before getting backstabbed.
Aizen is a bit difficult to quantify since he's supposed to be as powerful, if not more so, as when he was Death Metal-Aizen. He just doesn't really get a chance to show it due to the rushed nature of the series ending and he's fighting Yhwach mainly by dicking him around with illusions. Also, Aizen's immortal but we don't know to what degree. If we're going by Death Metal-Aizen standard then he's powerful enough to casually throw out mountain busters and he can combined at least five of those suckers with no problem. But even with that I'm fairly certain that Bijuu Madara outclasses him simply because that's the kind of fire power that the Juubi shrugged off like it was nothing.
Aizen might catch him off guard via illusion trickery but I'm not sure how much he can after getting to that point.
Alright, so Jyuubi Madara it is...
Dark Soul pretty much has it.
Aizen is meant to be stronger when he's in the chair than he is when he's all death metal style. I mean just the sheer bananas power he could bring to bear just by flexing his aura alone is actually incredibly nuts. Problem is, Madara is ridiculously hard to hurt and has a bunch of firepower and gimmicks he can bring to bear.
Kyouka Suigetsu is potent but to what end I guess...?
I'd back Madara myself.
Kyouka Suietsu still requires Aizen to show off his shikai, doesn't it? While Madara should be able to genjutsu Aizen just by making eye contact, even before taking into consideration things like the full moon Tsukiyomi plan, or whatever his "trap the entire world in an illusion" plan was called..
I'm not sure how the Sharingan's base ability to see through illusions works against non-chakra illusions, though.