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

[Paul Farquhar]

Forget about alignment, play the character.

 

[Dannyalcatraz]

Robert Howard Bruce (aka “Ether Man”) was a RW serial rapist who got caught after 20 years of crimes in at least 5 states. The detectives talking to him were very frustrated with him by the end of their interview.

One said to him (paraphrasing), “You’re smart, you’re good looking…you could have done anything you wanted!”

He laughed and replied, “I did!”

 

[Lanefan]

Smart (and wise) chaotic evil?

Job one: survive. Remember, if careless you can always be killed by the chaos you create.
Job two: never get caught. Plausible deniability is your friend, as are any and all means of defeating or obscuring divinations.
Job three: do whatever the hell you want while making sure others suffer the consequences.

Unwise CE types fail at job 1. Dumb CE types fail at job 2.

 

[Plaguescarred]

Smart Chaotic Evil to me is calculated, unscrupulous, without second thought remorses being free from any moral constraints or code of conducts limitation, usually self-centered acting without regards to life, laws, agreements. No wrong in their way, they can lie, cheat, extort, kill with ease.

 

[EzekielRaiden]

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, you have to articulate an idea of both Chaos and Evil that actually coheres.

"Chaos" is usually depicted as sloppy, slapdash, shambolic; to be of Chaos is to self-diminish because you can't get your poop together. To overcome this, we need a conception of chaos which is self-reinforcing, rather than self-damaging. And for that, we have a useful concept: Fractals. Most fractals are not the picture-perfect self-similarity you see in the famous, named ones like the Koch Snowflake or the Sierpinski Triangle. Most of them are random, messy things, which defy analysis by being complex no matter how close you zoom in. And that, in truth, seems to be one of the hallmarks of "natural" vs "artificial" things: natural things exhibit this infinite, down-to-the-molecules level roughness, which artificial things don't.

As for Evil, well, what's the typical problem with Evil? It's not just that it can be self-sabotaging, it's that it is easily tricked into doing something horrendously destructive for utterly unworthy payoff--petty self-centered nature, more or less. Chronic Backstabbing Disorder is another one, especially for those who blend Chaos and Evil. So what fits for this kind of Evil? I would say evil induced by absolute madness. Evil arising, not from a conscious choice to do a thing one knows is wrong, but from a genuine desire to do "good" things, warped by a profound derangement of facts and reasoning.

In other words? Something like Davros from Doctor Who, or perhaps Lex Luthor (especially the version in 2025's Superman). This kind of Chaotic Evil can be brilliant or stupid, physically powerful or reliant on skill and resources, an "ally" of convenience or a ruthless opponent, etc., etc. They just need some Purpose, some Worthy Goal, so that they can say: "Utopia justifies the means." Because once you cross that line, you functionally are Chaotic Evil. You'll do ANYTHING to make your utopian goal a reality. You'll kill anyone, destroy anyone, ruin lives, lie, cheat, steal, whatever it takes.

This is not a fickle CE. It is not a vacillating CE. This dispenses with the LoL rAnDuMb crap, and instead focuses on the overwhelming insanity of Chaotic Evil: insanity so sharp, it can duel. It's textured all the way down; you can never get a perfect bead on what it wants or why it's doing what it's doing, because no matter how finely you zoom in on its actions, it doesn't "settle down" into a clean pattern. The only thing so neat and tidy about it is its dedication to whatever it is that it pursues. The only method it follows: anything goes. Not in a grasping-at-random way, but in a speed-chessmaster kind of way: constantly re-formulating plans with every minute detail flowing in.

 

[AlViking]

It always bugs me when people automatically depict chaotic as stupid, undisciplined, unstable or uncontrolled while lawful is depicted as intelligent, stable, disciplined and strategic. Those aspects don't have much to do with how I view chaotic.

A chaotic person (good, neutral or evil) doesn't follow a moral code as defined by any external force, they don't have any guardrails as to what they will do. They'll honor a promise as long as it's in their benefit, they don't follow any code - pirate or otherwise - and while they can have goals and aspirations they may change them if they want. They don't have to be random destruction just for the sake of randomness, they can be cruel and creative in the suffering they cause for jollies.

Also remember that very few people are truly only one thing. They may have a soft spot for puppies or be a fey that cannot technically lie because of external enforced limits what they say but can still mislead, trick and be cruel like an evil version of Puck.

 

[aco175]

I like the Littlefinger example from Game of Thrones (GoT). He works within the system only when he needs to in order to push his agenda. He acts mostly in secret since he is not as powerful or playing the game of pushing others in certain ways. He cares for little except putting himself in a certain place. He freely murders or creates the downfall of others if it helps him.

Might be NE or CE but people are complicated and alignment is not a all the time thing. He helps people in certain situations, but only (that we see) because it helps him somewhere or at a point in the future.

 

[Bill Zebub]

Act Lawful, but secretly be sowing Chaos.

(Are references to political appointees also considered political speech...?)

 

[CreamCloud0]

To my own definition:

Evil: a willing capacity to harm or take away from others to benefit yourself, your goal and your desires.

Chaotic: liberty, a willingness to ignore or abandon anything or anyone that would hold you back from following your desires.

Now, there is nothing in those descriptions either separately or combined that prevents smart strategic thought or planning, where people go wrong I believe is in obligation, they think that evil is obligated to stab their friend in the back ‘for the evilz’ or that chaos is antithetical to following rules if they desire to, all that’s really between clown prince CE Joker from being a competent long term planner is the wisdom of exerting a bit of self/impulse-control.

 

[Li Shenron]

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

Can somebody explain how your GM would pull it off?

Someone with very high IQ who has a strong resentment against any form of authority other than themselves, and consciously refuses to care about the wellbeing of others.