I wasn't sure if this was the appropriate place for this question, so if this need be moved, by my guest- I just figured general discussion seemed a good area for flavor questions.
Specifically, I've recently come at odds with a friend over the meaning of wisdom, and whether it can be applied to chaotic characters in specific ways. He's a very law minded individual, which he recognizes, and has a hard time accepting chaotic characters offering valid philosophies and forms of wisdom that don't necessarily lend themselves to building, order, and structure.
I wanted to see if the community could aid me in providing examples of wise chaotic minded characters, preferably including a mix of good, neutral, and evil, that I could offer to him as suitable examples of both a chaotic orientation and qualify in the conventional sense as wise, whether they're canon pathfinder characters, or from any other fiction. Anyone got some good solid examples for me~?
Can a wise person believe in individual rights and freedom? Favor a person over people as a whole? Resent authority? Hate slavery and imprisonment? These are the chaotic principles that come to the top of my head at the moment.
It depends how you interpret law vs chaos alignmentwise. For me, it is in some ways almost a political debate - do you stress society or individuality, do you trust an overall ruleset to fit all cases and provide better outcomes overall or you think every situation should be judged individually. Basically, to me, someone who puts individual people as more important than social institutions, or codes of behavior leans towards the chaotic.
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Alignment is about goals and desires, while Wisdom (or any Ability score) is about capability.
So someone who desires freedom, particularly of personal expression, but shows good judgment, common sense, and perceptiveness in going about achieving that, is a high Wisdom Chaotic character.
In terms of real life, my immediate thought is most of the United States founding fathers. They wanted freedom and independence for themselves and many others (note how I don't say all or specify whwre on the Good/Evil axis they might've been...IO have opinions on that, but they're off-topic here), and went about that in a pretty methodical fashion, in some cases while indulging themselves personally in one way or another.
Ben Franklin is probably the best example of this, combining an immense number of stereotypically Chaotic traits in both his personal and professional life (helped start a revolution, notoriously promiscuous, had a bastard son he acknowledged at a time when that was odd, etc.) with a propensity for extremely good advice on a variety of topics (he basically came up with using 'Pro and Con' lists, wrote 'Poor Richard's Almanac', etc.), and finally succumbing to age at 84 after a long and successful career in several fields.
In terms of fictional characters, it's a bit harder. Fictional characters who epitomize Chaos tend to be high Cha and low Wis, as a rule, just as fictional characters representing Law tend to be the reverse.
That said, my first thought is Robin Hood's Merry Men. Depending on the version you go with, it's quite debatable whether Robin Hood himself qualifies, but generally at least one or two of the others (Little John leaps to mind in many interpretations) demonstrate Wisdom and general common sense, while remaining firmly on the side of Chaotic Good.
In terms of canon Pathfinder characters, Clerics of Chaotic Gods are definitely a good place to start. I'd particularly look at those of Desna and Calistria, as the tenets of Gorum and Cayden Cailean tend to lead to certain behaviors that some might not consider wise, making them less obvious in their Wisdom. Several Clerics of Desna in Adventure Paths leap immediately to mind.
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I wanted to see if the community could aid me in providing examples of wise chaotic minded characters, preferably including a mix of good, neutral, and evil
Chaotic good:
Core Concepts: Benevolence, charity, freedom, joy, kindness, mercy, warmth
Think about a cleric, listening to those in need. Many times he offers free advice or healing, but he won't always give them what they think they need. And sometimes he will outright reject a demand which looks reasonable on first glance. Due to his high Wisdom he is very capable of understanding petitioners, their real motives and and what's really best of them. He doesn't judge much, even not greedy or scheming petitioners, unless the person surpresses other people.
Chaotic neutral:
Core Concepts: Capriciousness, fate, freedom, individuality, liberty, self-possession, unpredictability
Think about a druid, usually busy with his own affairs. He insists on dressing himself like he wants, eating what he wants and bringing his pet bear into town. Due to his high Wisdom he is usually aware that he upsets people with such behavior - but he simply doesn't care. He also leaves other people to their own business, unless he notices they want to spoil nature or restrain him. Or his bear - which he considers an extension of himself and for which he developed an impressive empathy.
Chaotic evil:
Core Concepts: Anarchy, anger, amorality, brutality, chaos, degeneracy, freedom, profaneness, violence
Now consider a psychic with the psychedelia discipline. He consumes hallucinogens on a regular basis, some of them are so exotic that most commoners never heard of them. Depending on his consumption over the day (and night), his view of the world alternates between unnaturally clear and totally screwed up. The latter often results in bloodshed, without any appearant reason. Since he became used to recognize his own figments, he is surprisingly good at detecting oddities in both mundane and magical deceptions of others. Further, sometimes he has a deep understanding of his own flaws, but he considers it his personal freedom to cause mayhem whenver he wants.
PS: Kids, don't do this at home. If you to expand your mind, eat some almonds or fish. Omega-3 fatty acids are your friends. Drugs are not.
Using chaos to achieve one's ends, being at peace with a disordered state as natural, and accepting that one cannot plan for all outcomes, so the one who can adapt will win… plenty of wise chaotic outlooks.
Chaotic Wisdom + Intelligence can borrow from the Thirty-Six Strategems (warning: tvtropes link), many of which have a decidedly chaotic bent to them.
Or you can just stat up Bill Murray.
Silly example: Not allowed to walk at the left side of the sidewalk? Your wisdom will tell you that it is a completely unnecessary law. Breaking that law, encouraging people to break that law, would also make the right side of the sidewalks less crammed. And if there's no horse chariots around, why not walk in the middle of the road? Why not anywhere? It would just be better for everyone.
True wisdom would tell you that having a default rule splitting traffic into noncompeting lanes enhances efficiency in high traffic areas, and reduces it in low traffic areas. You should pragmatically vary your rule/no-rule mix according to the circumstance. Which is why ethically neutral people are the most wise.
actually, you'd need intelligence to perceive this assignation of traffic, THEN you may or may not have the wisdom to respect this sensible arrangement.
Zen Buddhism is surprisingly non-lawful in alignment. Many of their stories revolve around the message that you shouldn't take the rules to serious - you can't attain enlightenment while you're still attached to things, and rules count as things for this.
Since Zen Buddhism comes from a rather lawful oriented society, this makes them actually look mostly chaotic, but I think they just seem that way in contrast, and it's actually mostly neutral.
(After all, you can't attain enlightenment while being attached to freedom, either. You don't have to actually give up your freedom - or your laws - but you have to be *able* to give them up to become enlightened.)
As far as fictional examples that come to mind... Lirin, from The Way of Kings (I can't not cite this), Michael Garibaldi from Babylon 5 (more wise in the "common sense" variety than the stereotypical spouting philosophy, but still), Tom Bombadil.
I think part of the problem is the non-game-system-based characters are a lot harder to identify as Chaotic if they aren't going around breaking things, and obviously wiser Chaotic characters are likely to be a lot more moderate and patient, and just take issue with the bad rules and corrupt authority instead of hating the entire system without bothering to differentiate.
My favorite take on high-wisdom chaotic essentially comes down to this: Strife and disorder cause problems, but by nature, they cause lots of small problems. They don't enable the kind of large-scale systemic problems that stagnation and excess stability can. (Look up the lyrics of the song The Sun is Also a Warrior, it's a very nice example of the kind of philosophy I'm trying to communicate.) This was more or less the idea of my CG Inquisitor (deity being The Traveler, from the Eberron campaign setting), her opinion was generally that if people had too much authority or stability or tradition, they were likely to end up with a bunch of harmful and useless laws that wouldn't get changed just because change is scary.
Another one I've played around with for CG is just a very strong take on "mind your own damn business", to the point of almost pacifism. Someone hired you to do something about the goblins near their village? That's your responsibility, better do it. But you don't have any right to decide the goblins deserve to die - at least not without a much more nuanced understanding of goblin culture and the motivations of these specific individuals, and that would take a while - so better find a way to get the goblins to not interfere with the human village, with minimal encroachment on the freedom of the goblins to be goblins when it doesn't do any harm. Anything weird you see going on, if it doesn't do any harm, chill and don't be judgmental about it. If someone actually tries to hurt someone else, though, their right to freedom is limited precisely where it would interfere with anyone else's, and that's when you step in, albeit while doing as little harm as possible, at least until you know what the bad guy is doing and can be sure their motives aren't justified.
Uncle Iroh from Avatar, The Last Airbender (the anime, not that travesty of a movie) seems like he should qualify as chaotic good and wise.