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

A chaotic still has to exist in society.

They woukd need to be so powerful they can ignore things. Ir hide things.

D&D tends to be fairly simplistic. CE is evil stupid.

OPs asking about smart CE. IRL the violent types tend to end up dead or in prison. Non violent ones very unpleasant to be around.

A smart charismatic one might have devotees.
Societies tend towards lawful, though. Chaotic characters tend to end up the lone wolves away from that society, so as the chaotic evil person amasses power? They're going to break away from that society through one reason or another. Be it banditry or something else

And yeah, they need to be powerful. Chaotic evil is basically the alignment of might makes right, not caring about the laws and just doing what one wants.

Alignments don't exist IRL so bringing up how it works there won't really work. Frankly alignments are a crutch anyway. But if we're bringing it up, then we have to bring up Zenos as a fictional character who is very much chaotic evil and his one goal is trying to do anything to keep away the sheer grey boredem in his life, which very much quickly turns into wanting to fight you as you repeatably clash against him, getting stronger, until you beat him and, well. Spoilers once again.
With nothing else to live for, he kills himself after finally losing in a fight, the challenge of watching you grow stronger the only thing that has ever given him any happiness. Then his body gets brought back without him, and his soul ends up in someone else, and he, rather understandably pissed off, murders his way to getting back his original body and then promptly sets about causing a near world-ending catastrophe all to simply have another opportunity for the two of you to go one v one. He faces down the final boss of the game by asking you a simple "This is your prey? I thought you were above something so mundane", implying you're going to crush the final boss, and after you've killed what amounts to a god, asks you for a simple one versus one, until your lives are spent.

Zenos has devotees. But, he doesn't care about them. He lets them do whatever they want, only caring for anything to get him out of that boredem, and suck-ups do not get him out of it.
 

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