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

[Dannyalcatraz]

Chaotic Evil enjoys hurting people; hurting people feels good. Hurting people feels just as good when they're bad people, and usually even better. Hurting people is even better when someone else thanks you for it.

Richard Kuklinski was allegedly a professional hit man who got caught & sentenced. By the testimony in his case and subsequent interviews- if true*- he was legitimately a serial killer who had also found a way to monetize his passions.

Darkest version of “Do what you love, and you’ll never work a day in your life.”







* he confessed to over 100 killings, but was only convicted of 5. Investigators were unable to corroborate most of his confessions, but believed he was credibly guilty of at least 15.

 

[Lanefan]

As a player though, your "villain" character is supposed to win. And that can be really... icky. D&D is all about heroic fantasy where evil always loses. Pretty much every published scenario, right from day 1, presumes that the PC's are going to be heroes and they are going to win. The idea that your PC's go into (to pick a REALLY old example) Slave Pits of the Undercity, take over the operation and begin being slavers themselves is not supported at all by anything in the game. There is zero presumption that the PC's are going to join forces with the slavers. And, frankly, that's something that would be very uncomfortable to play out at most tables, IMO.

Pre-2e D&D didn't assume this so much. You might have been taking out the slavers in A-series for altruistic reasons, or because doing so promised lots of loot, or because they were competition with what you were doing yourselves.

It was 2e that (sadly) brought in the "PCs are expected to be heroes" vibe as a direct response to the Satanic panic of the day; while at the same time banning classes that might not be so heroic (e.g. Assassin). Stupid move then, stupid move now; and WotC has leaned into it big time.

When I ran some of the Slavers series a while back, one of the main PCs* actually had "Slaver" as her randomly-rolled secondary skill. This gave the party some extra insight into the slavers' operation but also meant it was entirely possible she'd talk the rest of the PCs into taking over the slaving operation, as this character hadn't entirely left her old profession behind...

* - her most famous quote, on the party subduing some bandits: "Stop taking prisoners, start taking inventory".