Chaotic Evil PCs

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I'm running a module for some new players. Half of them basically want to murder all innocent and benevolent quest givers in broad daylight in heavily populated areas, but ignore antagonistic monsters. I'm not opposed to the idea of running a campaign for chaotic evil PCs, but this module doesn't exactly accommodate it. I figured I'd try pleading with them out of character to just get through this one mission before flipping out and terrorizing the world, but I'm a little at a loss on how to set up plots, incentives, twists, and avoid party killing consequences once we're through this module. The ol' "please save my doomed village" quest probably isn't going to cut it.

Can a campaign designed for unpredictable psychopaths be successful? How do you even go about doing that? Are there any good ones already out there?

Any tips, tricks, advice, or anecdotes would be appreciated.



I will not ever DM for such a campaign. I play D&D for heroic fantasy. However, my players know this ahead of time. They know that if they choose to play their PCs in such a manner, there are two possible outcomes:


  • In game, the full consequence of their actions will be imposed. Much higher level heroes, deities, authorities will mete out justice.

  • Out of game, the player will be asked to bring it back to heroic play, or the player will be asked to leave the gaming group.


If this is a collective decision, and multiple players are taking it in this direction, I'll retire as their DM because I don't want to create adventures for a chaotic evil party.

If you do NOT want to DM for such a party, talk with your players. Be direct. And be firm.

However, if you are willing to DM for such a group, you will have to decide whether you are running as caterer to their desires and whims, or foil. Are you there to serve them up with innocent fodder for their evil cannon, or are you there to use NPC authorities to attempt to bring them to justice?  Either approach is legitimate, but require very different tactics.
Here are the PHB essentia, in my opinion:
  • Three Basic Rules (p 11)
  • Power Types and Usage (p 54)
  • Skills (p178-179)
  • Feats (p 192)
  • Rest and Recovery (p 263)
  • All of Chapter 9 [Combat] (p 264-295)
A player needs to read the sections for building his or her character -- race, class, powers, feats, equipment, etc. But those are PC-specific. The above list is for everyone, regardless of the race or class or build or concept they are playing.
I will not ever DM for such a campaign. I play D&D for heroic fantasy. However, my players know this ahead of time. They know that if they choose to play their PCs in such a manner, there are two possible outcomes:


  • In game, the full consequence of their actions will be imposed. Much higher level heroes, deities, authorities will mete out justice.

  • Out of game, the player will be asked to bring it back to heroic play, or the player will be asked to leave the gaming group.


If this is a collective decision, and multiple players are taking it in this direction, I'll retire as their DM because I don't want to create adventures for a chaotic evil party.

If you do NOT want to DM for such a party, talk with your players. Be direct. And be firm.

However, if you are willing to DM for such a group, you will have to decide whether you are running as caterer to their desires and whims, or foil. Are you there to serve them up with innocent fodder for their evil cannon, or are you there to use NPC authorities to attempt to bring them to justice?  Either approach is legitimate, but require very different tactics.



I think that Seeker pretty much states how I would handle this as a DM.  First before a campaign even started or characters were made I would sit down with the players and figure out what kind of game they wanted to play, and whether I was the kind of DM who could provide it for them. 

For an evil party I will tell them that as a DM I will treat behaving evilly as having consequences similar to attempting those same acts in the real world.  This would of couse apply only in the "civilized" portions of the campaign setting.  The party could stay in the "uncivilized" portions of the game world to avoid these messy consequences, but then they will be facing the beings which want to make them the victims of similar acts.  Either way with me as a DM, the life of the evil party is bound to be a short and messy one unless they become very good at disguising/hiding their evil behaviors.

I would make this very clear before the game even started, and ask that if they want something different, then they will need to choose a DM from among them to run it.  I'll be perfectly happy to destroy that DM's game campaign as a Chaotic Evil Prick if that's what they want to run.  I figure most of those games should be over in about 3 to 6 sessions anyway as they get pretty boring after a while.  Then I'll step up and offer a heroic fantasy game in its place.

I hope this helps.
If you do NOT want to DM for such a party, talk with your players. Be direct. And be firm.

That's sound advice. At present I really don't know what I want beyond participating in an engaging story. I think it's only fair I give it a shot to discover whether or not it's something I'd want to do long term. If it turns out it's not for me then your suggestion is probably my only option.
However, if you are willing to DM for such a group, you will have to decide whether you are running as caterer to their desires and whims, or foil. Are you there to serve them up with innocent fodder for their evil cannon, or are you there to use NPC authorities to attempt to bring them to justice?  Either approach is legitimate, but require very different tactics.

I think both of those mirror even the concerns a heroic campaign would have to take into consideration, is one there to serve up glory, riches, and victory or to provide heroes with challenging enemies that test their very limits? I definately think there is room for both whether the campaign is heroic or villainous. I just understand how to balance that much better in the heroic case, still struggling how to conceptualize that balance in an evil context.

First before a campaign even started or characters were made I would sit down with the players and figure out what kind of game they wanted to play, and whether I was the kind of DM who could provide it for them.

In retrospect I really ought to have done that. Since they are new players and I'm fairly unfamilar with DMing we sort of played fast and loose with the introductions and character backgrounds.

Either way with me as a DM, the life of the evil party is bound to be a short and messy one unless they become very good at disguising/hiding their evil behaviors.

That sounds good, but what do I do once they call that bluff? Is it really acceptable, knowing their general inclination, to have two dozen paladins waiting in the wings to drop them? In a heroic setting I can imagine taking flack for stuffing a room with too many monsters. I'd want to set it up so that it isn't any more difficult being evil than it would being heroic. If they get overly ambitious in either good or bad I suppose they get what they get. It's just a town square seems comparably less threatening than a dungeon full of hell beasts. I didn't want to tweak difficulty per se to convince them to play good guys or bad guys forced to act good. I didn't want to take a meta stance that crime doesn't pay or that villians have a tougher life. I'm just not sure how to do that or if it's possible.

I figure most of those games should be over in about 3 to 6 sessions anyway as they get pretty boring after a while.  Then I'll step up and offer a heroic fantasy game in its place.

I'm not sure how long it'd last, but it being more susceptible to boredom is possible. I think that may go back to Seeker's thoughts though, that a DM may become permissive to the point of handing them what they want. I don't see why the difficulty has to change or that it just become monotonous hack and slash. I get the impression the players might have gravitated to this as a backlash to the heroic setting.

I hope this helps.

Very much. Thanks.


I certainly don't mean to indicate a DM can't have a bash the helpless innocents kind of game if they want to run one.  Personally I think that kind of game would be rather dull for my tastes.  I also wouldn't dictate how the players play their characters, but I would dictate as DM how the world responds to their actions, and use the real world as a model for the response if they wanted a dark and gritty realism evil campaign over a high fantasy style good campaign. 

I'm pretty flexible with the kind of game I can run, but I generally don't to consequence free cakewalk worlds in any case.  If that is what a group of players want, then I'm probably not the right DM for them.  However, I'm not saying other DMs can't fill in that gap.

I hope this helps.
If you want an engaging story, this is definitely not the group for it.  These guys don't want a story or roleplay, they just want an excuse to vent their inner sociopath.
Another day, another three or four entries to my Ignore List.
I certainly don't mean to indicate a DM can't have a bash the helpless innocents kind of game if they want to run one.  Personally I think that kind of game would be rather dull for my tastes.

Apart from the general lack of direction, that's my biggest fear, that it will be dull. I'm thinking that might be because the innocent just don't seem very interesting or challenging adversaries, especially if they are helpless. Here's a setting with colorful villians and tons of really imaginative monsters. Compare that to your fairly bland good guy NPC who typically only shows up to provide exposition on the current quest. I'm speculating that an evil game could be interesting, but I guess i'd have to overcome the fact that the good guy NPCs are typically helpless and uninteresting. I'm not sure how to fix that.

I also wouldn't dictate how the players play their characters, but I would dictate as DM how the world responds to their actions, and use the real world as a model for the response if they wanted a dark and gritty realism evil campaign over a high fantasy style good campaign.

I'm not sure if realism is the best model to frame it in either. There are bad guys in these high fantasy style good campaigns, theoretically most didn't establish their evil empires overnight. I've been kicking around the idea that an evil party may sort of follow in what I imagine would be the tyrant boss character's footsteps from these heroic campaigns. I'm just not sure where to start.

I'm pretty flexible with the kind of game I can run, but I generally don't to consequence free cakewalk worlds in any case.

That's another worry of mine. I agree, a consequence free cakewalk isn't what I'd want either. That means sooner or later more challenging good guys will have to come out of the woodwork to stop them. I'm thinking I'd just have to tier it so it's roughly the same difficulty as monsters as if it were in a heroic tale.

I hope this helps.

It does.
If you want an engaging story, this is definitely not the group for it.  These guys don't want a story or roleplay, they just want an excuse to vent their inner sociopath.

I thought about that. I'm just exploring the possibility that there could be an engaging story about sociopaths. There's sort of a big thing for anti-heroes these days and the reverse dungeon setting does sound interesting, so I'm not convinced that it's impossible. I just wouldn't know what to plot hook chaotic evil characters with. The best I can come up with is make a stack of quest NPCs and let them eviscerate them one at a time until they either get bored enough to hear what they have to say or they say something that appeals to their twisted self interest.

I'm not entirely sure that it's just a wanton desire to kill everything. They seem disinterested in killing the intended antagonists out of spite. I'm thinking I might be able to get one of the main villians to recruit them or something.

Has anyone tried something like that?
You can make it that a major evil organization will "try to recruit them", as they are interfering with their business.

If they accept, you now have a superior that gives them missions (and it needs to be evil mission, like extortions, murdering, etc).

If not, bring the big and heavy hand of the law (with the help of the evil guild) to a showdown, where they then have two choices:

- fight and die (or go to prison and have to make a mission to repair thair ways; if failed again go to second option).

- run and become outlaws, at which point you can make their life a living hell (any major town guard would go after them, need to always live outside, low supplies, bounties would be posted and they would be attacked regularly by adventure companies, and if not enough, a big enough company would eventually be organized to track them and kill them outright); make it clear they CANNOT go evil all by their own.

Would you be targetting them? Yes, but thay made their choices, and they have consequences.

This, of course, if you actually WANT to run an Evil campaign, that takes A LOT of effort; i would talk with the players first, to establish the rules of the campaign (should have been a first step, easy mistake to make when starting and have no reference or guidance). 
It looks like the OP has received several pieces of good advice already.  Here's a couple of things I would do if I were running an evil campaign (though I have not actually done this, so there is the possibility that I don't know what I am talking about).

1. You can still scale challenges for an evil party.  The first time they do something openly evil some low level mooks from the local watch show up and try to arrest them.  They have the option to fight, or sneak away - both should be pretty easy.  If they fight, now they have a reputation for resisting arrest and fighting the law.  The next time they are spotted doing something evil, a larger and more capable force will be sent out to deal with them.  Similarly, just as you would give a good party a task that is easier accomplished with diplomacy or stealth instead of brute force, you can do the same thing for evil characters.  Good PCs may have to sneak into the temple of Lolth and rescue some captives who are destined for human sacrifice.  If they fight every drow they meet, the combat would be overwhelming and they would almost certainly die.  For evil PCs, it might be sneaking into the temple of Pelor to steal the sword of truth so it is not used against them.  Again, they need to come up with a thougtful plan because a straight up fight is suicide.  Don't reward stupidity whatever the alignment of the PCs.

2. Ask your players for some of their long range goals.  Do they want to become despotic rulers?  Do they want to run a powerful crime syndicate?  Do they want to hang out in a secret lair gathering magical power?  Make them come up with some purpose other than randomly slaughtering whoever gets in their way.  That may be fun for a session or two, but it's not something to build a campaign around (or at least I would not want to play in that campaign).

And as several people have said before, if you decide you don't WANT to run an evil game say so.  Lots of people will jump in and say that the DM should be accomodating and do whatever the players want, but a person willing to run games is a valuable commodity.  Don't underestimate the strength of the argument, "That's not the kind of game I want to run, maybe somebody else should DM for a while."
I heard that they are making a new video game, where you control the Netherese flying citadel of Sakkors, raining death on your helpless enemies below. Working title: Mythal Command.
You've gotten a lot of good advice.  I have a few more questions...

Do these PCs have back stories?  Where did they come from?  One thing that often trips up real sociopaths is that they cam from somewhere with people who saw them as children and saw indications of their sociopathic behavior, which can then be used by authorities (particularly once with access to divination rituals) to hunt them down.

Most players at this point will come up with back stories in which everyone who ever knew them are dead.  That, too, is unlikely to have occurred without notice by others.  Don't let them off the hook there and don't make the mistake of having the "good guys" coming to get them think that the PCs are likely to be converted to goodness. 

These players are not roleplaying.  They do not care about their characters -- except insofar as they allow the players to indulge their ids.  So they will care not one whit about any NPC you craft. 

This brings up another no-win scenario for you.  Since all they seem to care about is indulging their basest desires, there's not going to be much for you to do except give them more innocents to slaughter.  They aren't going to want to roleplay very much.  They aren't going to want to settle down.  They won't get involved in long story lines.  Even long-term villains won't intrigue them.  This is going to be a long slog of short-term goals and immediate gratification.   You need to think long and hard before sligning onto a campaign like this because it often becomes grueling and unrewarding for the DM.

I think running a campaign for evil PCs is one of the hardest assignments for even skilled experienced DMs.  I really can't caution you enough as a relatively inexperienced DM that this is going to be difficult. 
Rev Morbid

   Ok I have run an evil campaign or two and they are very debasing as far as DMn. Chaotic players play chaotic PCs but not always. As it was said earlier running an evil campaign takes work and thought to make players who just want wanton destruction and killing to be drawn into a real plot.


Now here is a plot I have used before and it worked rather well, and copying is a really nice way of flattery.
  Now if they are in some po-dunk little town or village they may not really run into any big resistance, but also there isn't a lot to steal either or you should make it that way. "You just got 6 copper and a silver off the guy you murdered." And use the right term too, MURDER, as killing is one of those debased words in this kind of game, and make sure there are witnesses all the time, people are everywhere. then they have to MURDER even more. Soon word will be sent out to the local lord for help, now he may send some weak force to deal with the insulent bastards, but don't let them kill all the force, say once 1/3 to 1/2 of the force is dead they run right out of town/village. Now they might get a break from the local lord forces for a week or two to cause more mayheme, but on return the lord  sends some undercover guys who are just one or two travelers to scout out the party. They stay to gather facts and t hen leave  back to the lord with their accessment. another way you could handle this is to have a guy try and come to join them he stays for a while learning their secrets and then leaves one day/night and back to the lord. Some pictures are made and printed off and sent to other towns and citys with bountys for the players HEADS, wanted dead or alive. You then send waves of stiffer and stiffer forces to come after them till and order of paladins/monks/whatever come into the the picture, these guys are a hard encounter of the parties level built out of monsters/npc about 3-5 levels above the party and be sure to go 1 XP below the next Target Encounter XP total for a hard encounter of the players level so if there are 5 players @ Lv 6 use a LV 9 encounter w/ an XP pool of 2499 XP. max it out! Drive them from the town/village and if they stay and fight kill them, award them for their actions properly. That what happen to bad folk in a game like that. never hint or tell them to run let them figure it out themselves, they were smart(err foolish) enough to get into this situation, let them get out of their trap. Now smart enemies put the kabash on fleeeing enemies by having a second force down the road, as your players might just decide to run down the road. All roads are guarded by lesser groups hidden in ambush waiting for the fleeing party. Oh ya give them a decree before you kill them, read off some charges the main opponent shout in the middle of the town/village.

   Then if they break through the line they can run to a neighboring city where they find their pictures up on the walls wanted by the king no less for MURDER, Theft, torture, crimes against animals, counterfieting, devil worship, and failure to pay proper taxes.  While in the city under cover they learn of an evil warlord in a nearby kingdom who has it in for the kingdom they are trying to escape from. Suddenly they are in a plot! He even has wanted posters of the PCs and is intriged by their actions and want to recuit them for his devious plans!

I just found something weird too. in my firefox there is a spell checker in Internet Exploder there is none

KSW
I don't understand the general consensus that 'evil characters automatically try to kill every innocent bystander they meet'.  Nor do I understand why the majority of DM's refuse to run a campaign with evil characters in it.  I've ran sessions and played in sessions that were evil, and they were nearly all fine, although I know I've been blessed with outstanding DM's through my RP'ing career.

I will agree that the 'kill bystanders whenever I can' evil party is boring as hell.  But people seem to think thats what evil is, when nearly every time I've played or ran it, its totally the opposite of that.  My players (and myself) have no compunctions against killing another person, but its always done as a last course of action.

imo, the biggest thing, is to find out what motivates them (your players).  In the best evil campaign I ever was a part of, the party motivation was power.  They brought nations who were allies against each other into full scale war against each other, they brought down huge houses and companies, assassinated rival factions, and in general masterminded some very nasty, evil things.  But they were careful, and were almost never implicated in anything, let alone actually prosecuted.  They ended up being some of the most powerful (not through straight head on combat, mind you, that was far too dangerous) people in the world, and only a very limited number of individuals actually knew they were running a big portion of the show, and they never knew how much.

Motivation is what drives people to play the game.  For some people, its to be the 'shining knight in armor saving the day' regardless of how well their character actually fits that visually.  For others, its being the one who's in a seat of power, public or not.  And honestly, those evil campaigns I've played where power was the goal, the group actually did quite a few 'good' things (destroying evil demons and devils and general 'bad' guys) but only because they got something out of it that propelled them farther up the totem pole.

Sorry for the wall of text, I just get frustrated at the close-mindedness of a lot of people when it comes to this particular subject.
You mentioned in your original post that you have a hard time trying to make the party care about the conflict you're trying to present them with. Keep in mind that evil is never monolithic. Just because your party is evil and your antagonist is evil does not mean that they are going to get along. Instead of a damsel-in-distress type character who needs help, drop the antagonists on them and give them a reason to go after the them.



I don't understand the general consensus that 'evil characters automatically try to kill every innocent bystander they meet'.  Nor do I understand why the majority of DM's refuse to run a campaign with evil characters in it.  I've ran sessions and played in sessions that were evil, and they were nearly all fine, although I know I've been blessed with outstanding DM's through my RP'ing career.



I could not possibly agree any more with this. Just because your characters are playing the odd end of the alignment spectrum doesn't mean that they are automatically bad people. If your players truly are completely uninterested in their characters and the story involved with them, then you should start to rethink the peple around you.

A certain few people in this thread seem to be coming in here on their high horse and jumping to the conclusion that because these people don't want to play knights in shining armor, that they are some kind of group of rabid sociopaths who don't care about story and only care about killing... An attitude that, in my opinion, is just as detrimental to the spirit of the game as the attitude they criticize.

EDIT: The Imperial March was playing the entire time I was typing this. Fitting.
Thanks to everyone providing suggestions. Definitely useful.

Do these PCs have back stories?  Where did they come from?

This is something I made the mistake of breezing by. These are first time players, pretty unfamilar with the setting and rules, I really should have done more but was a bit overwhelmed. They have names and very vague concepts that don't go much further than assumptions drawn from their stats and their class. I suggested they come up with backstories and some shared reason for working together, but I didn't want to force the issue. A couple of them have a very low opinion of their capacity for creativity. They may be a little too self conscious. 

These players are not roleplaying.  They do not care about their characters -- except insofar as they allow the players to indulge their ids.  So they will care not one whit about any NPC you craft.

I hadn't thought of that. Our group has been pretty bogged down just trying to introduce the rules. I don't think any of them set out to make a serial killer character, so I think you're right. I don't really have a character to hold them to. 

I think running a campaign for evil PCs is one of the hardest assignments for even skilled experienced DMs.  I really can't caution you enough as a relatively inexperienced DM that this is going to be difficult. 

Theoretically it doesn't sound tough. Besides being caught off guard, I think the reason it's tough is what you've pointed out. They just don't have much in the way of character to work from. I'm not sure how to patch that up. I suppose I could devote a chunk of a session to asking them character creating questions.
Now here is a plot I have used before and it worked rather well, and copying is a really nice way of flattery.

I like it. Like a net slowly being pulled around them. I'd just be a little hesitant to use that to promote a crime doesn't pay angle, but that is definately a solid way to explain increasing difficulty so I will probably be using a variation of that to some degree. Thanks.
I don't understand the general consensus that 'evil characters automatically try to kill every innocent bystander they meet'.

In my instance they are chaoticish, but you're right. Even in my situation, where it's increasingly likely it'll be an evil campaign, they pick and choose their targets. I think that's consistant with wrecan's observation that they aren't really roleplaying, but instead acting out against the traditional heroic convensions (atruistic protagonists, defense of the weak, ect).
imo, the biggest thing, is to find out what motivates them (your players).

lol, I'd guess spite for being placed in a setting that expects them to be heroic. It's a pretty short module I'm running and I thought it'd at least serve as a good introduction to the setting and mechanics before I take the leap and try to draw up plots of my own. There was some understanding prior to the start that they'd be helping this village out, but they either aren't taking the setting seriously or are wanting to push to see how dynamic this style of gaming is.
Sorry for the wall of text, I just get frustrated at the close-mindedness of a lot of people when it comes to this particular subject.

I agree to a degree. Evil gets a bad wrap, but that's sort of expected in high fantasy. Moral absolutism is just a pretty dominant theme and is bolstered by the cultural perspective these settings are typically set in.
Just because your party is evil and your antagonist is evil does not mean that they are going to get along. Instead of a damsel-in-distress type character who needs help, drop the antagonists on them and give them a reason to go after the them.

Yeah, that probably plays a lot into the problem. I'm not really satisfied with this module's plot hook, but it is sort of a beginner's adventure and I was just worried about getting the rules right. If I can get them through this I'll definitely keep that in mind and have some quests appeal to a more mercenary disposition.

A certain few people in this thread seem to be coming in here on their high horse and jumping to the conclusion that because these people don't want to play knights in shining armor, that they are some kind of group of rabid sociopaths who don't care about story and only care about killing... An attitude that, in my opinion, is just as detrimental to the spirit of the game as the attitude they criticize.

That's probably my fault for giving that impression. I think I called them psychopaths in my OP. I was probably exaggerating a little bit. It's just... the first NPC they meet they wanted to kill.

NPC: "You folks look like adventures. Our village could really use your help."
Them: "Ok. We stab 'em."

DM: "You come across a group of thugs. They stand in your path and insult you."
Them: "I want to role Dipomacy and see if we can get them to join us."
DM: "Err... ok. (DC too high), didn't make it."
Them: "Ok, we leave them alone."

Maybe I'm just clinging too tightly to this inflexible module, but I have a tough time imaging the sort of story they'd get their characters into willingly. I like the suggestions offered by a few of you here about making an on the run campaign where they are basically chased by public avengers, I just don't want to make it seem too heavy handed like the universe is out to get them. Appealing to a mercenary mindset seems like a good idea, but I'm not sure what they'd fight for. Letting them climb the ranks of evilness to horde and conquer seems nice, but many of the people here are right in that'd probably get boring. I'm just not sure what incentives can be used. It's easy in a heroic setting, but it doesn't seem like it's a straight 1:1 conversion between glory and infamy.
We are playing very dark characters in my group at the moment. I can give you a few tips our DM has used in making our party work together for the greater "good".

The first step is linking the party together. Breaking out of a prison as a quest is one way to force players to join together at least until their free. Another way is to give each player a section of map leading to untold riches. The players will plot ways to get the other parts of map on their journey to the location allowing their evil side to have a little fun.

It helps if the player characters are smart, assassins and thieves as opposed to thugs and brutes. It is also a good idea to make death a major problem for the players. When they know their character cannot come back they plot their moves carefully, framing others for their ill deeds because anyone who tries to kill a chaotic evil character is not going to find forgiveness.

When you want to run a conversation make sure you have loads of guards that the group dare not attack, this will allow you to offer information or give out quests without the party attacking the NPC.

Chaotic Evil PC's seek unlimited power and so you should set quests that offer that power but only as a group. For Example: The God of Destruction has a long lost temple where it is said he waits for Six (number of players you have) Chaotic Evil adventurers to receive his otherworldly powers.

This will force players to keep each other alive but kill all that stand between them and the power of a god. Upon finding the temple it may be a trap designed to sacrifice the evil characters to bring the god into the mortal world.

This could be the hook for making your players create new less evil characters as the god has been set free and plots to restore his power and rule the world.

Evil characters can be a lot of fun but they never last. As DM you should inform the group that their characters may have a very short lifespan if they want to kill, lie and cheat. The law always catches up with you in the end.

Hope this helps. And don't think it's impossible, just think evil.
Just in case I failed to mention; I am playing D&D 3.5e.
I don't understand the general consensus that 'evil characters automatically try to kill every innocent bystander they meet'. 



In this case, it's because the OP stated that that's what the players have expressly stated that they want to do, in the first two lines of the initial post of this thread.
Another day, another three or four entries to my Ignore List.

I will agree that the 'kill bystanders whenever I can' evil party is boring as hell. 



The reaction is primarilly against this kind of evil character as being the only "typical" chaotic evil mode many players can conceive of playing.  I agree with you that well thought out characters with sound motivations and goals can be fun to play and run regardless of their alignment.  What I generally can't abide as a DM is a group of players of any alignment who want a consequence free cakewalk campaign with no challenge.  Adventurers who wantonly slaughter the helpless (be they peasants or "evil" goblin children) strike me as this type.

Will I run an evil campaign with players who a) know how to work together as an evil party and b) have a workable character concepts which understand and coordinate on their long term evil goals?  I most certainly would, and have a fun time with it.  Will I run a game for puppy chucking knuckleheads?  Nope.

I hope this helps.

p.s. as I noted in my first post it isn't the chaotic evil character which is so horrible, it's the Chaotic Evil Prick who's such a pain.
What bothers me about evil PC's is the artificiality of the direction of their evil.  Namely that it sounds like your PC's want to kill every NPC they encounter, but don't want to kill eachother.  That's a really big role-playing inconsistency.  

Sure, there could be an interest in sticking together at first, but what happens when one of them gets their first nice magical item?  When they have to split up loot?  When one of them on watch and realizes that if he kills the others he can collect the bounty on their heads?

Evil plotting against the world could make for a fun campaign, but evil plotting between PC's is a huge headache.  I find that it is the sort of thing that rapidly ruins games.  D&D is not designed as an adversarial game, and the mechanics of PC v. PC don't work well (what's a diplomacy check on a PC supposed to do? or an intimidate?).  

So your players could just decide that they work together for the entire campaign, and they could plot to take over the world, or leave a path of bodies behind them, but I find that inconsistent role-playing.  I wouldn't be surprised if a couple players in this group turned on their fellow PC's at somepoint, and then you have a huge headache on your hands as the DM.

At the very least, figuring out how they work together is a something to consider.  If I were going to attempt this kind of campaign, I'd have a very early encounter place a powerful curse on the PC's.  The curse would somehow bind them together (maybe the spirit of a powerful demon is split into pieces and each enters one of them), making it so that they cannot hurt eachother and cannot lie to eachother.  It's artificial, but it could be necessary.   
If they like killing so much, teleport them to a Tomb of Horrors type dungeon and make it a survival/battle royal type of game (could be a part of the Underdark).

To not make things so boring for you (just basically random encounters), make some zones territory of a few social races/individuals that actually manage to make a living there.
If they like killing so much, teleport them to a Tomb of Horrors type dungeon and make it a survival/battle royal type of game (could be a part of the Underdark).

To not make things so boring for you (just basically random encounters), make some zones territory of a few social races/individuals that actually manage to make a living there.


Not a bad idea, that.  I played through the World's Largest Dungeon for a little while in 3.5 and something that was a big part of that dungeon was a wide variety of fairly cutthroat societies competing for the same living space.  A band of mercenary adventurers with no respect for life might be quite a blessing down there.
If they like killing so much, teleport them to a Tomb of Horrors type dungeon and make it a survival/battle royal type of game (could be a part of the Underdark).

To not make things so boring for you (just basically random encounters), make some zones territory of a few social races/individuals that actually manage to make a living there.


Not a bad idea, that.  I played through the World's Largest Dungeon for a little while in 3.5 and something that was a big part of that dungeon was a wide variety of fairly cutthroat societies competing for the same living space.  A band of mercenary adventurers with no respect for life might be quite a blessing down there.



I was also thinking about the Ultima Underworld setting (computer game), just exchange falsely acused with truly belonging there with "the scum".

What bothers me about evil PC's is the artificiality of the direction of their evil.  Namely that it sounds like your PC's want to kill every NPC they encounter, but don't want to kill eachother.  That's a really big role-playing inconsistency.  

Sure, there could be an interest in sticking together at first, but what happens when one of them gets their first nice magical item?  When they have to split up loot?  When one of them on watch and realizes that if he kills the others he can collect the bounty on their heads?



That is the other misconception a lot of people seem to carry when it comes to evil rp games.  One group (the oldest, in fact) refuses to play anything even close to evil because they assume that either they themselves or another PC will very quickly backstab everyone else for their own immediate betterment.

Apparently the 'strength in numbers' axiom only applies to good guys and npcs.  The way I look at it, from the perspective of gaining power, good things come to those who wait.  Becoming a supremely powerful being is not a quick process (PunPun excluded, ofc).  So, prior to becoming immortal, or at least a demigod, I have zero reason to kill ANYone who's going to actually help me obtain that status.  Ok, he has a badass sword I could use to gain a small bit of an edge over my immediate opposition.  Why not let the guy who already has it use it, so he can keep helping me achieve MY goals?

Makes no sense to me to weaken myself by offing my allies before they've outlived their usefulness.  And, as said above, prior to being AT LEAST a demigod, having a big guy in front of or beside me swinging that sword is going to be infinitely more useful than me doing it all on my own.
A good example of a group of Evil making it work would be the Decepticons. Sure, Starscream keeps backstabbing Megatron, but outside of that, Soundwave shows genuine loyalty to Megatron, even if he's a snake to some of his allies to maintain his position of power. It's one thing to be evil, but you can possess emotions outside of avarice and hatred. Even Blofeld had a pet.

However, I will concede that most players are not thinking that deeply on the subject. They are usually looking to be either sinister or ridiculous, and have little intention of taking an evil campaign seriously.
The Smithy Knew He'd Lost His Groove When Scalding Sparks Left His Chin Too Smooth Dwarvenshave
Chaotic Evil PC's seek unlimited power and so you should set quests that offer that power but only as a group. For Example: The God of Destruction has a long lost temple where it is said he waits for Six (number of players you have) Chaotic Evil adventurers to receive his otherworldly powers.

I think that encapsulates what I'm looking for. Converting what would be a good deed quest into a bad deed quest. The opposite of rescuing a villiage, helping someone find a lost relative, stopping an unjust ruler. that sort of thing.
What bothers me about evil PC's is the artificiality of the direction of their evil.  Namely that it sounds like your PC's want to kill every NPC they encounter, but don't want to kill eachother.  That's a really big role-playing inconsistency.  

I don't necessarily think so. Even IRL some of the most vicious and sadistic murderers had family, friends, and associates they got along with. Both good and evil characters have the capacity to be hypocritical when it comes to the criteria they use in evaluating the value of life.
Will I run an evil campaign with players who a) know how to work together as an evil party and b) have a workable character concepts which understand and coordinate on their long term evil goals?  I most certainly would, and have a fun time with it.  Will I run a game for puppy chucking knuckleheads?  Nope.

lol. Reminded me of this, Never Split the Party: Unless One of Them is a Video Gamer.
Makes no sense to me to weaken myself by offing my allies before they've outlived their usefulness.  And, as said above, prior to being AT LEAST a demigod, having a big guy in front of or beside me swinging that sword is going to be infinitely more useful than me doing it all on my own.

The mafia comes to mind. I think the misconception is coming from the same place Lawful Stupid comes from, it's an exaggerated caricature of the general attitude.
A good example of a group of Evil making it work would be the Decepticons. Sure, Starscream keeps backstabbing Megatron, but outside of that, Soundwave shows genuine loyalty to Megatron, even if he's a snake to some of his allies to maintain his position of power. It's one thing to be evil, but you can possess emotions outside of avarice and hatred. Even Blofeld had a pet.

This is an excellent point I hadn't thought about. Within the broad category of evil are plenty of archetypical villians. Even within the smaller catagory of chaotic evil, their values and motivations influence their relationships.
I don't necessarily think so. Even IRL some of the most vicious and sadistic murderers had family, friends, and associates they got along with. Both good and evil characters have the capacity to be hypocritical when it comes to the criteria they use in evaluating the value of life.

A good example of a group of Evil making it work would be the Decepticons. Sure, Starscream keeps backstabbing Megatron, but outside of that, Soundwave shows genuine loyalty to Megatron, even if he's a snake to some of his allies to maintain his position of power. It's one thing to be evil, but you can possess emotions outside of avarice and hatred. Even Blofeld had a pet.

Both of these points address the same concept: that evil *can* work together and have relationships.

In the Decepticons, the only one who believes himself to be the equal of Megatron is the backstabber.
In the mafia, if you show yourself to be equal to your superior, one of you is going to be eliminated.
A gang leader may have trusted lieutenants. He does not have the luxury of trusted equals.

Evil requires hierarchy. But a gaming group is generally assumed to be a party of equals, not Player A and His Lackeys.

Here are the PHB essentia, in my opinion:
  • Three Basic Rules (p 11)
  • Power Types and Usage (p 54)
  • Skills (p178-179)
  • Feats (p 192)
  • Rest and Recovery (p 263)
  • All of Chapter 9 [Combat] (p 264-295)
A player needs to read the sections for building his or her character -- race, class, powers, feats, equipment, etc. But those are PC-specific. The above list is for everyone, regardless of the race or class or build or concept they are playing.
I can't give anymore advice then what was given, but I will say this is the reason I never let my players play evil PCs.  More then likely it ends bad
I can't give anymore advice then what was given, but I will say this is the reason I never let my players play evil PCs.  More then likely it ends bad

Think it's fairly clear that situation typically ends badly. Exploring how and why is interesting.
Evil requires hierarchy. But a gaming group is generally assumed to be a party of equals, not Player A and His Lackeys.

That's an astute observation. I suppose to some degree even a party of good adventures can have some informal leader. 4e is really pushing the idea that clerics, bards, and traditional support classes of all classes are leadership roles, lol. That may be a fundemental point to reconcile for the evil party, that there is some formal or informal pack mentality that makes one of the PCs the alpha dog. I can see where that wouldn't work for everyone though. I almost perfer to play lackey characters; moff tarkin, weyoun, wormtougne. I don't think most players do though, that may be why evil campaign parties have cohesion and direction problem.

I'm not convinced that an inherent distinction between good and evil is in leadership struggle. It is a strong motif though, good being framed as selfless and thus more willing to cooperate. I don't know though. Can someone be evil and selfless? lol.


Evil requires hierarchy. But a gaming group is generally assumed to be a party of equals, not Player A and His Lackeys.

That's an astute observation. I suppose to some degree even a party of good adventures can have some informal leader.


I would say that for low level evil parties, an outside leader is a must to keep the campaign from collapsing; not only it serves as a boss that gives them missions, but also serves as a menacing figure, the "obey me or else" so useful to the DM; it will probably also be the first arch-enemy the party will try to face, so it adds hooks as well on its own.


 4e is really pushing the idea that clerics, bards, and traditional support classes of all classes are leadership roles, lol. That may be a fundemental point to reconcile for the evil party, that there is some formal or informal pack mentality that makes one of the PCs the alpha dog. I can see where that wouldn't work for everyone though. I almost perfer to play lackey characters; moff tarkin, weyoun, wormtougne. I don't think most players do though, that may be why evil campaign parties have cohesion and direction problem.


To this, i will simply quote the PHB1(pg16), regarding the leader role:

"Clerics and warlords (and other leaders) encourage and motivate theri adventuring companions, but just because they fill the leader role doesnt mean they are necessarily a groups spokesperson or commander."



I'm not convinced that an inherent distinction between good and evil is in leadership struggle. It is a strong motif though, good being framed as selfless and thus more willing to cooperate. I don't know though. Can someone be evil and selfless? lol.


Absolutely:

- paladins that believe their faith should be the one and only

- burocrats and advisors that just hinder the efforts of the heroes to help the realm/organization

- anyone who believes in a cause but without seeking personal beneficts, that believes that the ends justify the means.

Basicaly most of the NPCs that in other editions would fall under Lawfull Evil. 
 Can someone be evil and selfless? lol.



Did you see Serenity? The Agent is a classic example of extremely evil and totally selfless. 
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Apparently the 'strength in numbers' axiom only applies to good guys and npcs.  The way I look at it, from the perspective of gaining power, good things come to those who wait.  Becoming a supremely powerful being is not a quick process (PunPun excluded, ofc).  So, prior to becoming immortal, or at least a demigod, I have zero reason to kill ANYone who's going to actually help me obtain that status.  Ok, he has a badass sword I could use to gain a small bit of an edge over my immediate opposition.  Why not let the guy who already has it use it, so he can keep helping me achieve MY goals?

Makes no sense to me to weaken myself by offing my allies before they've outlived their usefulness.  And, as said above, prior to being AT LEAST a demigod, having a big guy in front of or beside me swinging that sword is going to be infinitely more useful than me doing it all on my own.



I think this is possible, I just think that over the length of a game it will become artificial.  In a good or neutral group there is a sense of loyalty within the group.  There might be individual opportunities for individual PC's that they don't seize because they are beholden in some way to the group.

In a long campaign it seems highly likely that opportunities will arise for individual PC's to seize more power by betraying the group.  This won't happen all the time, but an evil PC played consistently should be willing to make a deal with enemies when it is to their own personal advantage.  It's possible to maintain an evil alliance, I'm just saying it's far more difficult, and potentially artificial.  

Also, in my experience, players who want to play evil PC's of the type the OP described (the kill everyone type), will quickly grow bored and that at least one of them will want to turn on the other PC's.   

Also, in my experience, players who want to play evil PC's of the type the OP described (the kill everyone type), will quickly grow bored and that at least one of them will want to turn on the other PC's.   


Agreed, Evil campaigns will tend to have a VERY short span, unless something forces them to stay together.

Or you could go the Paranoia route: everyone knows the Stasis Clone spell, and everyone will have clones, with the memories up to the clone process; this will get old too eventually. 
I would say that for low level evil parties, an outside leader is a must to keep the campaign from collapsing; not only it serves as a boss that gives them missions, but also serves as a menacing figure, the "obey me or else" so useful to the DM; it will probably also be the first arch-enemy the party will try to face, so it adds hooks as well on its own.

^ That is sharp. I like that.

To this, i will simply quote the PHB1(pg16), regarding the leader role:

"Clerics and warlords (and other leaders) encourage and motivate theri adventuring companions, but just because they fill the leader role doesnt mean they are necessarily a groups spokesperson or commander."

That last line should also include "or respected." Tee hee hee.
Did you see Serenity? The Agent is a classic example of extremely evil and totally selfless. 

I did. Good film and solid example. I suppose I should have framed the question as, can a chaotic evil character be selfless? I'd imagine the Agent as more of a lawful evil, but I may be wrong. We're dealing with a lot of abstract concepts so it's tricky for me to picture. Maybe it's really the chaotic part of chaotic evil that is throwing me off.
Also, in my experience, players who want to play evil PC's of the type the OP described (the kill everyone type), will quickly grow bored and that at least one of them will want to turn on the other PC's.   

I think the answers I've gotten to my last question provided some clues to why that might be. Maybe it isn't so much the evil dimension that grows monotonous, but the chaotic? Maybe it's because a pack of maraudering looney toons have embraced an exaggerated version of chaos and never latch onto anything in the environment/story to have any resonance? I don't know.

Has anybody had any trouble with chaotic characters in the past? Any similarities?
In that context I do think the chaotic part of chaotic evil maps to the self serving element.  Unfortunately too many players treat it as maping to the illogical and random kind of character instead of self serving personality with a cruel streak.  I think it is perfectly possible for a chaotic evil character to follow their societies rules when they are being observed.  It is only when they feel they can "get away with it" that they probably should perform their evil deeds.  Most selfish and cruel people generally don't want to be caught and punished for it. 

That leaves this random violence type of character in the insane category with most likely a psychosis, or aberant behavior mindset.  These are the kinds of evil character concepts I generally won't permit in any of my games.  Mainly because the players generally just want an excuse to act like puppy chucking knuckleheads.  I'm just not willing to create a playground for their twisted little sadistic power fantasies.  To do so that would have to make me the DM being willing to play the masochist to their sadist, and that's certainly not what I consider fun.

I hope this helps.
I suppose I should have framed the question as, can a chaotic evil character be selfless?


Complex charactaers can.  Imagine someone like Dexter.  Someone who is a self-acknowledged sociopath.  He is driven to commit horrific acts of violence.  He enjoys committing horrific acts of violence.  So he satiates his desires by seeking out other evil people and torturing them before murering them in some sort of poertic justice.  He's not lawful -- he cares not one whit about a code of honor, or mortal laws, or anything that is generally the hallmark of lawful behavior.  And he's not good -- even if he justifies his behavior as some sort of vengenace kick, he does horrible things with gusto. 

If hunting man is the Most Dangerous Game, how much more dangerous is it to hunt dangerous killers?  He knows what he does is dangerous, and that eventually, he'll bite off more than he can chew and his prey will become his predator, but he enjoys it too much to stop.

That's chaotic evil and it's selfless.

I doubt that's what your players are going for, though.
I have found this thread a rather interesting read. I concur with much of what I have read posted here. I thought I would toss in my 2 cp...
Your original post reads as if you all are relatively new and that the players just want to go around and kill things so they want to be evil so that they are not restricted in what actions they can take. Perhaps I am reading into it too much, but that is what I believe you are asking.
1st, I strongly agree that if this is not the game you want to run, then let the players know, and don't run it. It will not go well, you will get frustrated at DM and try to railroad the group too much and it will end up more a conflict between you and the players and no one will have fun. This could turn these new people off from the D&D game or damage friendships, so be sure that it is something you will enjoy doing.
2nd evil campaigns can be done, but there are a lot of pitfalls. New DMs often fall into these problems, so I would suggest only an experienced DM run an evil campaign.  Issues with motivating the PCs, getting the PCs to do certain actions, obtain certain info, characters getting too powerful and unbalanced, etc. can be challenging and easily alter the game to where it is no longer under control.

If you want to run an evil campaign, structure it such that there are reasons for the PCs to be evil. Give them motivation and direction without controlling them, a tough line to walk sometimes. They need to feel soem kind of allegience to something to give some structure to the game. They could work for an evil kingdom that wants them to find an evil artifact. Or perhaps there is war and they are sent to do whatever damage they can to the other side (which means in their home country's villages they hopefully will not kill the town defenders). Or they are escaped slaves freed by an earthquake from their mindflayer masters (which would make them mentally unstable but later soemone could reform to good or at least unaligned). Or as others suggested, use a module or dungeon delve where it doesn't matter their alignment because they are fighting evil monsters in a dungeon. If you prefer to use civilized cities and they kill people, perhaps motivate them not to by having invading orcs or goblins raiding more frequently and as the town guards die (from the PCs as well as warring with the goblins), the PCs find less and less city worth living in. They could decide to join the orcs, but maybe the orcs turn on them, which shows them you can't trust all evil people.  Or go to an extreme and have them as the only human survivors of a cataclysm (would work good for a darksun type campaign) and they need to try to survive.  They may occasionally meet another human, elf, dwarf, etc. but they may want to keep the species going and not kill them off, and perhaps learn from them.
If you find you have a player in the group who WANTS to do more character in depth playing, give him a special quest during character generation to spy on the other characters. Perhaps someone wants to bring them to justice or someone wants the artifact they are sent after for themselves. Perhaps give each PC a side quest or task so that they ahve a reason to work with the others but also to do things for themselves. It would create more cautious playing rather than just killing everything in sight.
All that being said, I have played in a wide variety of games with a wide variety of people, both being the DM and as a player. Evil games rarely last long because it is hard to create any storyline that everyone will be interested in.  Also people get killed off quickly, either from other players or becasue they just want to kill things and get in over their head.  Anytime I have let soemone bring in an evil character, or been a player ina  game with an evil character, the game grinds to a halt and nothing really fun/interesting/productive happens in a game session and the players all get bored or frustrated and the game ends.  If their only interest is killing monsters it will get boring quickly. Perhaps run a few pre-made modules to get DMing practice and see what the players like and don't like. I have been in 1 evil campaign that seemed to work, it was in more recent years, but it was a module series so it didn't really matter the PCs alignments.  It was going after drow, and we were sent from Zentil Keep to investigate. The game went fairly well, even though we eventually got on different sides of a dispute and the last game was player vs player, but everyone knew it was coming so we were fine with it.
I think I gave more than 2cp worth so I'll end my input here. Hope you find some of it useful. Remember, the game is for everyone to have fun, so don't feel forced into something that won't be fun for you. If the DM is not ahving fun, it shows in the game and over time the players will stop having fun too. So find something you like.
DnD is not really set up for evil players.

Evil creatures have very different goals then heroes.  Evil creatures achieve these goals in very different ways. 

Evil creatures attain the goals through political means, taking a army to smash a nation, making deals with higher powers.

The rules and game mindset do not lead to good evil games.

I think you need a whole different game with a whole different set of rules to play a evil game
I can't give anymore advice then what was given, but I will say this is the reason I never let my players play evil PCs.  More then likely it ends bad


Of all the campaigns that I've been involved with (as DM and as player), it has been 2 evil campaigns that have lasted the longest and been the most memorable. It can be done, and done well, as long as the characters are in agreement of their goal and the players are friends(and not going to pull dick moves on each other). It certainly is a different game, but it's enjoyable and interesting.
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I can't give anymore advice then what was given, but I will say this is the reason I never let my players play evil PCs.  More then likely it ends bad


Of all the campaigns that I've been involved with (as DM and as player), it has been 2 evil campaigns that have lasted the longest and been the most memorable. It can be done, and done well, as long as the characters are in agreement of their goal and the players are friends(and not going to pull dick moves on each other). It certainly is a different game, but it's enjoyable and interesting.



Im playing in one right now:

- setting: 4th Ed Forgotten Realms, Moonshea Isles

 - party of pirate genasi, lower lieutenants.

 - no PvP allowed, although a situation arose where only one member noticed a trap but chose to keep it to himself, nearly made my PC fall into it (decided to not use out-of-character info); cant wait to get a chance to return the favor ;P

 - working for a pirate captain which is in search of a couple of mystic artifacts; it will be a race to see who gets to off him first ;P

  - 2 sessions only, so too soon to tell if the campaign can survive or not; the DM has experience in playing an evil campaign, but not running one.

  - team has NO teamwork, affects the combats.
- no PvP allowed, although a situation arose where only one member noticed a trap but chose to keep it to himself, nearly made my PC fall into it (decided to not use out-of-character info); cant wait to get a chance to return the favor ;P

^ That's good. I suppose there's no guarantee players won't stab each other unless it's explicitly stated no PvP allowed, but I very much like how it seems your group has managed to retain that uneasy alliance vibe despite that. I'll have to brainstorm some other situations like that where players can get a little underhanded without tearing the party apart.
- team has NO teamwork, affects the combats.

It sounds like the campaign is still fresh, so that's to be expected to some degree. All the heroic campaigns I've played have had minimal teamwork in combat early on. If it's just character disposition then I think I'd have to underscore the lesser of two evils to get them to cooperate, let'em know abandoning their defender/leader/striker/controller isn't going to make their task any easier.
Evil creatures attain the goals through political means, taking a army to smash a nation, making deals with higher powers.

The more I've been thinking about this the more I'm of the opinion that the difference in approach to goals isn't one of alignment as much as the distinction between PC and NPC. Evil creatures go about doing things in these heroic settings the way they do because they are narrative devices and must abide by the setting's conventions. That sort of thing is lampshaded in Austin Powers with the exchange between Dr. Evil and Scott over execution techniques. The villian takes these zig zag strides to achieve their goals because the straight line method is too effective and anticlimactic.

That's the problem I think I'm having. The PCs are just too effective when they play evil because they aren't bound by the same forces that make the bad guy screw up enough to give the heroes a sporting chance. They play smart and evil isn't suppose to be that smart because the villian isn't suppose to win.

Think it may be resolvable if either the players embrace the necessity of a convoluted path to success or if their nemesis will instead. The first noticeable silver lining in this is that at least virtuous antagonists have a better inherent excuse for taking prisoners.

I think you need a whole different game with a whole different set of rules to play a evil game

I think it's workable, but I agree that this game clearly isn't tailored to an evil party in even remotely equal parts as it is for a heroic one. They don't exactly even make it welcoming to play certain good character of races expected to be evil. Poor gnolls. One supplement text on evil campaigns would probably dispel the impression an evil game is impossible. All it'd need is a bit of fluff, DM advice, and maybe a few specialized mechanics for flavor and to compensate.
I would say that for low level evil parties, an outside leader is a must to keep the campaign from collapsing; not only it serves as a boss that gives them missions, but also serves as a menacing figure, the "obey me or else" so useful to the DM; it will probably also be the first arch-enemy the party will try to face, so it adds hooks as well on its own.

^ That is sharp. I like that.

To this, i will simply quote the PHB1(pg16), regarding the leader role:
"Clerics and warlords (and other leaders) encourage and motivate theri adventuring companions, but just because they fill the leader role doesnt mean they are necessarily a groups spokesperson or commander."

That last line should also include "or respected." Tee hee hee.

While using NPC leaders is a useful trick and tactic, it should be done carefully as not to set up a player vs DM mentality. The NPC should not be a bully, maybe in personality but not in actions. This isn't to say that they shouldn't feel threatened by the NPC.

In my longer lasting evil games, there was always a player leader who was calling the shots and organizing the approach. In both cases it was an evil paladin with a world domination agenda, and the other players were content, if not happy, to use his cause as a means to power and glory. It certainly helps when your players respect each others' characters and acknowledge each others' competence.

Also, in my experience, players who want to play evil PC's of the type the OP described (the kill everyone type), will quickly grow bored and that at least one of them will want to turn on the other PC's.   

I think the answers I've gotten to my last question provided some clues to why that might be. Maybe it isn't so much the evil dimension that grows monotonous, but the chaotic? Maybe it's because a pack of maraudering looney toons have embraced an exaggerated version of chaos and never latch onto anything in the environment/story to have any resonance? I don't know.

Has anybody had any trouble with chaotic characters in the past? Any similarities?

This board is filled with tales of chaotic players ruining games, especially those who are doing things just because they can. The problem I think is not so so much chaotic characters but chaotic players. A chaotic character can be an interesting (though still sometimes difficult) if they are roleplayed well. A chaotic player is usually uninteresting and often difficult, breaking the flow of the story and game. Usually chaotic players get bored with this and will drop out or actually start investing in their characters. It remains to be seen what your players will do.
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I love it when Players want to play Chaotic Evil Characters...The Instant their first level evil scum walk past the Town Cleric and his Detect Evil, they are rounded up at spear point by the Militia and stoned to death.

"We dont Want your Kind in these parts!"

Just put some Red Robed Mace wielding Militia on the town Gate and conduct a compulsory Detect Evil. After a few Weeks in the wild with no Supplies, Bounty Hunters on their Arses day and night so that they can no longer get the time needed to rest and meditate for spells, your serial killing trash (players PCs) will be begging for mercy.
The Citadel Megadungeon: http://yellowdingosappendix.blogspot.com.au/2012/08/the-citadel-mega-dungeon-now-with-room.html
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