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

[Marc17]

Build up a reputation of not-evil and not-chaotic so you can blow it on something big.

 

[Koloth]

Q in some episodes of Star Trek Next Generation.
Empress Sato in the Star Trek Enterprise episodes "Through the Mirror Darkly".

IMO - a CE critter doesn't think of itself as CE. It is just doing what it thinks is best at the time or as part of a longer term plan. The side effects of its plans on others don't really bother it one way or the other. Some of those effects may help others. Other effects may harm others. In its mind, so what? As long as its plan or status is improved. Or it just has fun.

 

[Kurotowa]

The Joker

Really, there's two flavors of CE. On "alignment is a personality chart" there's the clinical psychopath who lacks empathy for others or respect for the law. Which like I described, they can assemble a moral code from first principles on a purely self-interested utilitarian framework. And then there's "alignment is a cosmic force" where CE is the nega-inverse of LG that breaks things and hurts people out of moral duty.

Many recent depictions of the Joker trend towards the latter there, where he's trying to embody CE principles out of a twisted belief that up is down and Evil is good. And that's certainly a tact you can take with the alignment. But it's hard to describe that as "smart" CE.

 

[Toe Knee Nose]

Chaotic Evil, as was mentioned, is unrestrained, but, domineering. They are going to try to dominate anyone they perceive as weaker, while realizing they have to play it cool with those stronger.

Heck Hasbin Hotel is a good example.