I would say Falstaff from Shakespeare would be CN. He's a fun-loving, cowardly, treacherous lout, and he doesn't care who knows it. He's quite upfront about it, in fact.
On that note, I would say that a character's perceptions of how he relates to society make him lawful or chaotic more than his actual deeds. Both a lawful character and a chaotic character might use loopholes and corruption to get what they want. A lawful character would make that his primary plan, though, and then try to weasel out if things went wrong. While a chaotic would have no problem stabbing their enemies on the street if that whole "cunning" thing didn't work out.
CN would also encompass the anti-social type, I think. Especially classic movie gangsters like Scarface and Little Caesar. They're not evil in the "destroy the world" sense, but they know what they want and they're going to get it, and if laws or innocent people get in their way, that's too bad. Again, they're willing to use the law if it suits them, but their first impulse will be to simply ignore it and rely on themselves.
Samuel Fuller did a film noir called "Pickup on South Street" and he had an interesting note in an interview. He said that criminals were the most broad-minded people he'd ever met: they all had a racket, and knew everyone around them had a racket, and just figured that everyone needed to make money. Tell them the worst things about yourself you can, and the only thing that'll interest them is how they can profit from it. The lack of judgement is what keeps many of them neutral, I think.
