D&D General How do you do smart chaotic evil?

Right but you aren't willing to discuss what it actually means to be chaotic - it's just automatically insane no matter who it applies to. Is Ash insane? Deadpool?
The only Ash I know about is from Pokemon and he isn't CN or crazy. Deadpool I've considered to be insane since he first appeared. The Punisher is also insane, though he's LE in his insanity.
Are all the people who feel like they don't feel like they fit into society, have no respect for laws, authority or established hierarchies and just want to do their own thing but don't break laws because of the consequences insane?
No, but they aren't all CN or CE, either. Most are just neutral. The thing with neutral is that you don't have to have respect for laws, authority or hierarchies, and would just want to do their own thing. Most of the people in the world are neutral. They don't believe in Law, Chaos, Good or Evil strongly enough to move into those categories. They just want to do their own thing.

Chaotic is viewing those things as things to resist. It's the opposite of lawful, not the absence of lawful.
 

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The only Ash I know about is from Pokemon and he isn't CN or crazy. Deadpool I've considered to be insane since he first appeared. The Punisher is also insane, though he's LE in his insanity.

No, but they aren't all CN or CE, either. Most are just neutral. The thing with neutral is that you don't have to have respect for laws, authority or hierarchies, and would just want to do their own thing. Most of the people in the world are neutral. They don't believe in Law, Chaos, Good or Evil strongly enough to move into those categories. They just want to do their own thing.

Chaotic is viewing those things as things to resist. It's the opposite of lawful, not the absence of lawful.

Let's take a different approach. I have a character I want to represent. They don't care about laws one way or another, in modern terms they're libertarian. They just want to be left alone to do what they think is best - no regulation, no one telling them what to do. They may do some things on a whim but they aren't going to jump off a cliff because the idea pops into their head. They still accept responsibility for their actions and know what they do has consequences.

They certainly aren't lawful, they think laws and regulations are stupid, government is ineffective and should just get out of the way. They want a society where people work things out between themselves. What alignment are they?
 

They don't care about laws one way or another, in modern terms they're libertarian.
Libertarians say they don't believe in laws up until the point where you punch them in the face and take their "property" and all of a sudden the "non aggression principle" is something that I'm supposed to be following as if it's law.
 

I blame the current climate, but I can't imagine a smart chaotic evil.

Can somebody explain how your GM would pull it off?
Well first of all you have to understand Alignment isn't personality. It also isn't Intelligence. A CE can be smart enough to avoid consequences, they can like to hang out with people they can want attention. They can even have weird normal mortal problems like not being able to stand the sight of blood. They just believe they should be able to do anything they want. Quit tying personality to alignment, they are two different things. On the extreme end CE could be a timid school teacher who carefully plans the deaths of those who cross her or who have the money she needs to live in the style she wants too. A little poison, dispose of the body, move on.
 

Well first of all you have to understand Alignment isn't personality. It also isn't Intelligence. A CE can be smart enough to avoid consequences, they can like to hang out with people they can want attention. They can even have weird normal mortal problems like not being able to stand the sight of blood. They just believe they should be able to do anything they want. Quit tying personality to alignment, they are two different things. On the extreme end CE could be a timid school teacher who carefully plans the deaths of those who cross her or who have the money she needs to live in the style she wants too. A little poison, dispose of the body, move on.
This is true... one could say, if arguing personality and "smart" in absolutes, that LE are incapable of being "smart" as well. Considering flexible and creative thought are more approaching the domains of Chaos, if you arguein an absolute, personality basis, you may say all Lawful characters lack independent wits. sudden brilliance from some unknown well is chaos. The classic idea of "either he's a genious or a complete moron". The Nutty Professor is extremely "smart" scientifically, but he sure is a chaotic hot mess.
 

No edition has a CE write-up that doesn't involve insanity. I've seen no CE examples in media that don't involve being off your rocker in some way.

This is 3e's take on CE.

"Chaotic Evil, “Destroyer”: A chaotic evil character does whatever his greed, hatred, and lust for destruction drive him to do. He is hot-tempered, vicious, arbitrarily violent, and unpredictable. If he is simply out for whatever he can get, he is ruthless and brutal. If he is committed to the spread of evil and chaos, he is even worse. Thankfully, his plans are haphazard, and any groups he joins or forms are poorly organized. Typically, chaotic evil people can be made to work together only by force, and their leader lasts only as long as he can thwart attempts to topple or assassinate him."
Keep in mind also that those definitions are trying to portray evil in the most negative light possible, in order to make evil characters less attractive to play.
I think AD&D's CN is dysfunctional. It goes past insane. As for 3e's CN, first and foremost they follow their whims. Whims are done without thought. As an individualist first and last, while a CN person doesn't intentionally go after organizations or deprive others of liberty, if the whim strikes, they wouldn't hesitate to deprive someone of their freedom.
I think you're a bit too hung up on "whims" with all this, at least in the immediate sense. A whim "I'm gonna overthrow the king and put myself on the throne!" might lead to years of - perhaps on-and-off - planning and buildup in order to make that whim reality.

A CN or CE person can also be mostly an instigator of trouble, looking to cause chaos and disruption on a scale bigger than personal.
If your entire outlook on life involves following whims, you aren't a rational person.
Entirely depends on what those whims are and-or lead to. Rational does not equal logical.
 
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Libertarians say they don't believe in laws up until the point where you punch them in the face and take their "property" and all of a sudden the "non aggression principle" is something that I'm supposed to be following as if it's law.

I knew a guy who believed the ideal society would be a libertarian one with no laws or regulations. He considered taxes a form of theft and regularly quoted Reagan's “The most terrifying words in the English language are: I'm from the government and I'm here to help.”

All I'm going to say is that I disagreed then and I disagree now, more than that gets into politics.
 

Was Jack Sparrow insane? He was certainly CN. His choices are driven by freedom, survival, and whimsy rather than ideology or cruelty.
And yet even Jack (who I agree is CN) has some long-term planning underlying his whims - he knows where he wants to end up but his methods of getting there are entirely made up as he goes along.
For that matter I know people in real life I would consider CN - they obey the law not because they respect it, they obey the law because they don't want to end up in jail. Because they aren't insane.
Ayup.
 


And yet even Jack (who I agree is CN) has some long-term planning underlying his whims - he knows where he wants to end up but his methods of getting there are entirely made up as he goes along.

Ayup.
Agreed. Jack is a whimsical dude who loves freedom and hates the rigid hierarchical structures of most social order, which is why he chooses to live as a pirate. He's also smart and cunning (two related but separate things). Hell, when we learn what got him in a bad way in the first place, he actually looks more CG than CN. (Remember that the thing that got him in trouble was setting free the slaves in the hold of his ship.)
 

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