Chaotic Evil tidbits roleplay advice?

[Rosatine]

Hi there,

Basically, I'm just after any little pieces of advice anybody could give me on playing a chaotic evil character!

Just to briefly set the scene - two of my close friends and I are starting a new campaign, only three of us are playing (with a fourth likely joining) - and we have an incredible DM.

Now out of genuinely pure coincidence, all three of us have rolled evil characters. In fact, all three of the different evil alignments. I rolled a Chaotic Evil Warlock. (We also have a NE Gith and a LE Triton). So thankfully I won't have to worry about the 'playing an evil character in a good party' aspect.

This is the first time I've played an evil character! And what's more, I really do imagine my character as pretty dang chaotic, and pretty dang evil. But that being said - I still want everybody to enjoy the game!

I've read *general* advice on playing an evil character, for example, having a good a reason why you'd actually go on any quests at all, and 'save the princess' for example. So, having read the 'general advice', my question is -

Does anybody have any 'small' bits of advice? Little anecdotes perhaps? Things they've done that have been evil (preferably chaotic) and exciting, but not detrimental to the game, or 'stupid'? The last thing I want to do is annoy the other players or the DM.

How did your very evil character treat 'the quest giver'?
How did they go about general social interactions? Shopping, drinking at the tavern, etc.
How did they deal with confrontation?
What's the most evil thing they've done that everybody at your table was cool with?
What are some little 'everyday' examples of evil/chaos?

Etc. Etc. :)

I suppose I'm worrying that either I won't come across as evil - or ill try too hard to be evil, and I'll come across as 'chaotic stupid'. I'm fairly imaginative, but honestly any inspiration or little hooks would be so massively appreciated to help me on my way!

Apologies for the slight wall of text! Thank you for reading :D

[Wizard_Lizard]

ah... Chaotic evil, all of the fun stuff of chaotic neutral, and with none of the few morales...
My advice, go nuts, be selfish, do what you want, call all who disagree overbearing fascists... ...and when in doubt of how evil you are... ...I dunno, kick a puppy or burn down a village or something...

[Hail Tempus]

Remember that "Chaotic", in the context of D&D, doesn't mean "random." Your character may have no problems with committing horrible acts, and he has little to no concern for laws, the lives of others, or societal expectations or traditions. But, he shouldn't be engaging in random acts of stupidity and violence for no reason.

So, attacking the quest giver or the town watch for no reason isn't chaotic evil, it's chaotic stupid. The character needs to work within the context of the party and cooperate with the other party members to advance their collective agenda. If you feel that "my character wouldn't act like that", it's time to roll up a different character.

[KorvinStarmast]

Now out of genuinely pure coincidence, all three of us have rolled evil characters. In fact, all three of the different evil alignments. I rolled a Chaotic Evil Warlock. (We also have a NE Gith and a LE Triton). So thankfully I won't have to worry about the 'playing an evil character in a good party' aspect.
How is it that you rolled up a chaotic evil alignment?

Did your DM have you roll a 1d9 and see what alignment you ended up with?

[HappyDaze]

But, he shouldn't be engaging in random acts of stupidity and violence for no reason.


At the same time, those reasons don't necessarily have to be well considered or logical in the least.

[strangebloke]

Depends on how you define alignment. People argue over this a lot but ultimately, the only definition that matters is the one your party agrees on.

Definition 1:Alignment is a Tendency
So 'chaotic evil' just means that you're generally selfish and actively like breaking the rules when you can get away with it. You're in the 1/3 of people that are most selfish and most disrespectful of authority, but that's not really such a big deal in the grand scheme of things. Working with this definition, playing a chaotic evil character is easy. You're a hooligan. You hate policemen. You hate 'do-gooders.' You're out for yourself, but if it doesn't cost you anything you can and will help people out. After all, no harm in saving a man. He might help you later!

Definition 1:Alignment is Alignment to an Outsider
'Chaotic Evil' means that you're literally in the same bucket as demons. For this, you need to work with your DM to come up with a justification why you're doing the same thing as your allies. Maybe you're setting up a grand betrayal. Maybe you're trying to kill your master's rival demon princes. Maybe you're fighting something like the Elder Eye which even Demons oppose. Overall this requires a lot more work. Be sure to cackle. Ham it up. Don't take this too seriously as you don't want the other players to genuinely think you're a bad person. ....but at the same time, even going with this definition, you should need actual reasons to do bad things. Don't just... eat people for the evulz. have a clear reason why you want the world to fall to demonic corruption. Have rules for yourself. Maybe even make shows of altruism out of your own self-interest.

[NecessaryWeevil]

As Strangebloke suggests, even Chaotic Evil people don't have to be complete monsters. They can have redeeming qualities and admirable values - although the way they pursue those values may not be especially admirable.

You asked for examples: my Lawful Evil warlock despised those who abused their power, especially those who abused or neglected children. So, in Curse of Strahd, she (privately, untraceably and actually quite mercifully) executed a woman who'd given her kids away to hags. The part also came across a man trying to drown a kid in a lake...we capsized his boat and watched as he drowned.

[Rosatine]

Remember that "Chaotic", in the context of D&D, doesn't mean "random.''.......

I completely agree with all of this! However, what I have (some) difficulty with is balancing this trying to not be random, with a personality traits such as --''I get pleasure out of other people's pain.'' or ''I love mayhem'' -- To me, these sort of traits are almost inciting randomness. I mean, you instigate a tavern brawl because you love to see people hurt and see all the 'chaos' - although you do have a purpose, doesn't it more or less amount to just being random anyway?

I realise that might be a bad example, but I hope you can see my dilemma. Because I really do want to play 'chaotic evil' without doing this 'I'm going to punch every innocent person I see, (because I love violence and chaos!)' etc etc.



How is it that you rolled up a chaotic evil alignment?...

Honestly, I was reading 3.5's ''Fiendish Codex I: Hordes of the Abyss'' - and I just absolutely loved all the lore surrounding it all. I went on to read ''Fiendish Codex II: Tyrants of the Nine Hells'' - but the Devils didn't appeal to me even half as much as the Demons did. That's where the idea sprang from, it was definitely my choice.

And don't get me wrong, I have thought about this a lot. I just keep on reading things online I wouldn't have thought of in a thousand years. Which is why this advice is so valuable :D


'Chaotic Evil' means that you're literally in the same bucket as demons. For this, you need to work with your DM to come up with a justification why you're doing the same thing as your allies....

All of what you've said here really hit the nail on the head so far as my train of thought so far! I personally like the idea of ''Maybe you're fighting something like the Elder Eye which even Demons oppose.'', i.e. we're banding together to fight something even we want to get rid of. However, since we haven't actually started the campaign yet, I have no clue on the specifics.

Also, I definitely want the rest of my group to know I'm outright evil, I absolutely want to have fun! And maybe 'ham it up' a little as you've said :D That aspect isn't so much of a problem because as I said in the original post, the whole group is evil. but I still want to try and roleplay well and not annoy anybody!

I really don't want to be starting the ump-teenth fight of the session just because 'woah guys, we're evil'. On the other hand, I don't want to have done absolutely nothing evil or chaotic the whole session.

--

A couple of things I read last night that I loved the idea of (and were fantastic inspiration) were -

1). Using Suggestion/Command (or similar spell, or even outright persuasion) - to convince a religious character to denounce/desecrate/defile their god/place/item of worship. Maybe a quest giver desperately wants me to save their husband? ''Well I could iiiiffffff you spit on your holy symbol'' -- I love this, as to me it really shows the 'evil' of the character, yet it's only a fairly small act.

2). Using illusion magic of some description for nasty pranks. So, hmm, I don't know, thinking on the spot here:
- Sleight of hand swap the innkeepers pen for my dagger.
- cast some illusion on the dagger to make it look like the original pen.
- innkeeper goes to write something - then he's going ''argh my hand!!!!''
- chaotic evil character is laughing their face off (or secretly laughing their face off perhaps).

Ok, admittedly that's a bit long winded, and that's a lot to go unnoticed. But I like the 'idea' - Again, it's a relatively small act that is generally both chaotic and evil in nature. However this does lead me back to my first point right at the top, why would my character do this? The only reason is surely they'd think it's funny? Is that a reason? Isn't that random/'chaotic stupid'?

--

I hadn't even considered the whole 'corrupting innocents'/'defiling religion' before I read point 1 last night. Now when I'm thinking on my character, I can incorporate that in to some roleplay.

I hadn't thought that tricks can very easily veer between alignments simply by the nature of the things involved. Sleight of handing the pen for a stick of chalk, for example, wouldn't really be evil at all. So now I'm thinking 'what other tricks are there I can occasionally pull'?

Is the frequency of these acts the solution to all this? Even complete 'chaotic stupid' is ok, as long as it's not three times a session?

I'm just rambling now, but thank you all for your in put so far!

[Monster Manuel]

The key to playing an evil character is giving them a genuine motivation, which fits into the narrative of the adventure.

At one point, many editions ago, I was playing a lawful evil hobgoblin storm cleric in an all-evil party. The campaign started with a coordinated break-out from prison, which was fun, but the next adventure didn't go that well; we rolled into town and encountered a wererat infestation. Met the "quest-giver", etc, as if it were a typical heroic party, but the group had a tough time figuring out why we should care. Ultimately I think we just stole some food and moved on.

What was missing was a reason for these villains to get involved. In hindsight, what would have worked was something like "you come across a small town which would make an ideal new base of operations. There's even an abandoned manor you could inhabit. But when you try to move in, there are these pesky wererats making things difficult for you. Even worse, tomorrow the Sherriff is sending word to the Duke to send help, and you don't want the Duke's monster-hunters poking around your new lair, so you've got 24 hours to make the wererat problem go away". Boom, motivation for the evil party to get involved, rather than "Oh no! Wererats are attacking the town, help!", to which we responded "LOL, no".

Lawful Evil is about doing what you must at any cost. Neutral evil is about "what's in it for me?" Chaotic evil is about giving yourself advantage by exploiting someone else, or destroying something inconvenient. Chaotic Evil maliciously wrecks stuff for fun and profit. To play Chaotic Evil well, every choice should come down to "How can I use this to make things worse for X?".

What you need from your DM is a plausible X that you're out to wreck, and the recognition that the rest of your party are useful means to that end.

You can play the CE character as a schemer, who recognizes the need to keep a low profile. Going shopping for material components? Sure, you play the part, smile a bit at the merchants, lay on the charm. They might be useful later, there's no reason to kill them now, ROI vs risk is too low. Town guard is rude, tells you to move along? Of course, officer, right away, and what was your name again? Guardsman Travis, so nice to meet you, keep up the fine work you boys are doing. You add Guardsman Travis' name to your List...later in the campaign, maybe as a Downtime activity, you find out where Guardsman Travis' parents live and burn down their shed.

Chaotic Evil plays the long game...

[GlenSmash!]

Chaotic evil (CE) creatures act with arbitrary violence, spurred by their greed, hatred, or bloodlust. Demons, red dragons, and orcs are chaotic evil.

There are lot of ways you could play a character that would fit that description.

So here is my favorite CE character I've played. Most of the time he tries to be a decent fellow, but sometimes he violently murders someone, arbitrarily spurred by his bloodlust. Most often this occurs following a combat encounter like an overly brutal description of a killing blow. But no always it is after all arbitrary.

Afterwards he'll pretend he feels bad about it particularly to the party, and maybe he does feel bad about it at little bit, but he feels good about it a lot more than he feels bad.

Overall this guy pushes the line of what's acceptable to the party without ever feeling like I'm deliberately trying to disrupt the game or play Chaotic stupid. It feels like a flawed and more realistic type of CE to than someone that tries to set every NPC on fire.

[KorvinStarmast]

Honestly, I was reading 3.5's ''Fiendish Codex I: Hordes of the Abyss'' - and I just absolutely loved all the lore surrounding it all. I went on to read ''Fiendish Codex II: Tyrants of the Nine Hells'' - but the Devils didn't appeal to me even half as much as the Demons did. That's where the idea sprang from, it was definitely my choice. OK, so you rolled up a character and you chose the CE alignment.
Glad your other party members also signed up to play for Team Evil.
Best of wishes on your campaign. Have fun. :smallsmile:

[JeenLeen]

Search for Red Fel's thread on evil characters. He gives very good advice.

Other folk here give good advice. I could see a tendency like "steal, kill, or hurt when possible, as long as it doesn't hurt your plans", where "your" is by expansion the party's. Try to think of a reason your PCs work together and, ideally, care about each other. Even evil people have friends and loyalties. Even chaotic evil can. Yes, be selfish, but part of your "self" is your idea of your allies.

[Warped Wiseman]

I'm currently playing in an evil party for Dungeon of the Mad Mage, and one of the affects has ironically been to make our adventures less violent. This is because our party is more willing to negotiate with monsters that other parties would just slay 'because they're evil'. Alternatively, on at a few occasions we have sided with the 'bad guy' in a conflict, or fought characters that other parties would ally with.

Some things that have really helped keep our party together:
- All of our characters are working together for the same reason: they want to gather power to accomplish their long term goals.
- None of the characters view the other party members as a threat to their long term goals. None of their goals are mutually exclusive
- We started the campaign with the characters already having a professional respect for each other, which has grown in to something like friendship over the coarse of the campaign. They trust each other enough that they are willing to help out when one of them has a personal 'side quest', understanding that they will be helped in turn.
- We have made a number of mutual friends and enemies. This means that when those friends need help or those enemies are on the move, we are united in our response.

The biggest takeaway, as other people have pointed out, is to remember that just because you are evil, doesn't mean you need to go around kicking puppies all the time. It just means that you are willing use a wider set of tools when dealing with a problem.

[HappyDaze]

The biggest takeaway, as other people have pointed out, is to remember that just because you are evil, doesn't mean you need to go around kicking puppies all the time. It just means that you

... are happy stomping on the puppies' heads when such opportunities are presented.

If you're going to play CE, then don't be hesitant to embrace the chaos and evil that it embodies.

[firelistener]

I ran an evil campaign once. It's also why I ban my players from playing Evil alignments now. The most evil thing they did, I think, was accept a quest to pick up a slave from a slave-trader to bring back to the Zhentarim, do so, and abuse and torture the slave "for lulz". I won't go into detail, but it was pretty gross and they thought it was just hilarious. Personally, I see a lot of players use Evil characters as an excuse to do and say things that normally would be inappropriate for the table.

Please don't be like them. Just my opinion, but I'd much rather have someone play a Disney villain than a legitimate psychopath.

[JackPhoenix]

Remember that "Chaotic", in the context of D&D, doesn't mean "random." Your character may have no problems with committing horrible acts, and he has little to no concern for laws, the lives of others, or societal expectations or traditions. But, he shouldn't be engaging in random acts of stupidity and violence for no reason.

Definition of CE 5e is "CE characters act with arbitrary violence." They may have their reasons... perhaps the character simply doesn't like that guy's face. CE has nothing to do with laws or authority, CE characters *are* violent psychopats. That's what makes them CE.

[GreyBlack]

In terms of playing Chaotic alignments, I always recommend people not play it as "OMGRANDOMZZZZZZZZZZZZZQ". That can lead to frustrating your fellow players and sucks. Rather, I always recommend emphasizing the freedom aspect of the alignment; you're all about tearing down social structures for your own benefit. However, you need people to help you in this conquest; hence why you have allied yourself with the party. You're all working together to amass power for your own ends.

You are working with a LE character; I might recommend that you work with his character and arrange that you agreed prior to the campaign to work together and tear down the regional government. While you are doing it for the sake of tearing it down, they'd be doing it to build it back up in their own image. Just some food for thought.

Inb4: I recognize that I'm operating off an outdated definition Chaos. Too bad. Enjoy my personal suggestion. 😜

[Laserlight]

Silvereyes was a CE-to-NE warlock. He followed his employer's order...because he thought that would be a route to the power and money he wanted. He didn't go around murdering innocents, mostly...because he didn't want the hassle of town guards coming after him. He helped the party...because they were useful to him (and he explained that if any of them got to be a liability, he'd kill them). He would have betrayed anyone if he thought that would be to his advantage, stolen anything if he thought he could get away with it. In fact, when I retired that character, I took the party treasury with me.

The problem that makes CE into "Chaotic Stupid" is that people play it as if they could do whatever they want with no consequences at all.

[Shabbazar]

He helped the party...because they were useful to him (and he explained that if any of them got to be a liability, he'd kill them). He would have betrayed anyone if he thought that would be to his advantage, stolen anything if he thought he could get away with it. In fact, when I retired that character, I took the party treasury with me.

The problem that makes CE into "Chaotic Stupid" is that people play it as if they could do whatever they want with no consequences at all.

Shouldn't the consequence of your CE statements and/or play been that the party tells you to go adventure elsewhere? Why did they bother to associate with you?

Presumably you don't feel you were playing Chaotic Stupid, yet telling the party that you will kill any members that become a liability seems like a really quick way to exiled from play.

[Duff]

To re-phrase advice given above with slightly different emphasis:

Think about why your 3 characters will stay together for the campaign. Why do they put up with any poor behavior* from each other? Why don't they direct more poor behavior at each other?

Then the GM needs to be able to motivate that party - Depending on who's involved and to what extent the GM has already prepared the campaign, you may want to shape personalities and motivations which will go (more or less) with the campaign, OTOH, if the GM is very flexible, all that may be needed is for you to tell the GM where your buttons are to make your character go, Nothing kills immersion like having to accept a quest for which your character has no motivation to allow the game to go ahead.

Talk about limits - As noted above, and in other posts, an Evil campaign is more likely than others to head into territory some people are uncomfortable with. Talk about how specific everyone is happy with. For example, there's no need to describe horrific acts - You can just say "My character is going to have some nasty fun in the town we just conquered" and leave it at that, or you can be specific.
If your group of players can't talk about limits, you probably shouldn't do an evil party.



*poor behavior being everything from the little niggles of nasty pranks through to stealing each other's stuff and killing each others significant NPCs or betraying each other's quests and goals

[Tanarii]

Definition of CE 5e is "CE characters act with arbitrary violence." They may have their reasons... perhaps the character simply doesn't like that guy's face. CE has nothing to do with laws or authority, CE characters *are* violent psychopats. That's what makes them CE.
Agreed, at least for 5e definition of Chaotic Evil. But not necessarily all the time. It's important to remember Alignment is just one aspect of personality traits, and it's not necessarily even the dominant one, especially in situations where the other traits are more specific. But playing a CE character at the least means being considered the dangerous and unstable one.

OP, probably your best bet it to write out the 5e typical alignment behavior for 5e Chaotic Evil, and explicit Personality, Ideal, Bond and Flaw. Then consider how they interact or which is dominant in any given situation. That's my general advice anyway, but for an Evil character I feel it's more important than usual.

In particular, you can do something interesting with a high Cha warlock, like make his Personality a jovial and friendly who likes to crack jokes. And also give him a strong Ideal and commonly applicable Bond, that gives him focus other than being the arbitrarily violent guy.

[redwizard007]

CE, my second favorite alignment. Ah, the memories...

Dont go for homicidal maniac, well, not initially. My favorite CE character was a pretty solid guy. Cheerful, friendly, the kind of wizard that could have out charmed most bards. Happy to help out random town #3 with their orc problem. And then I happily retrieved my undead minions from the farm house they had been feeding in and commenced to meet the rest of the party. See, people didn't have value to me beyond the uses I could put them to. Killing a family for new zombies was just like going to the blacksmith for a new sword. The hard part was switching back and forth from charming to uncaring.

[Lunali]

Don't plan ahead too much or, if you do, don't stick to your plans. Do whatever benefits you most in the moment.

[BarneyBent]

You’re evil, so you’re generally willing to do self-interested things even if they cause problems for other people regardless of whether you like them or not, and would happily do something that greatly negatively impacts someone even if it only benefits you slightly.

You’re chaotic, which means you’ll probably do those things by actively disregarding or undermining laws and norms to do so, rather than a lawful character who may rely upon persuasion and deceit while navigating these laws and norms to fulfil their aims.

Put simply, you’d be more inclined to rob a bank than run a Ponzi scheme.

[Laserlight]

Shouldn't the consequence of your CE statements and/or play been that the party tells you to go adventure elsewhere? Why did they bother to associate with you?

Presumably you don't feel you were playing Chaotic Stupid, yet telling the party that you will kill any members that become a liability seems like a really quick way to exiled from play.

I was hoping for some pushback from the rest of the party, but apparently nobody saw a problem with it.
And several party members really were Chaotic Stupid, despite what was written in the Alignment box. To the point where I, the CE tiefling warlock, was the party bank.

[GlenSmash!]

I was hoping for some pushback from the rest of the party, but apparently nobody saw a problem with it.
And several party members really were Chaotic Stupid, despite what was written in the Alignment box. To the point where I, the CE tiefling warlock, was the party bank.

Yeah that was my experience as well. Playing a CE character but somehow still being the most reasonable member of the party.

[greenstone]

I take inspiration from media sources. So, what media characters are chaotic evil?

The Joker, obviously. Would be interesting, but would probably get killed by all the other characters, because if you look up "team player" in a dictionary, it has a photo of the Joker and a note saying "NOT THIS GUY!"

Agent Smith. "The purpose of life is to end." Hmmm, could do something with that.

Alonzo Harris. Claims to be one of the good guys (and might actually believe it) but is as corrupt as they come.

SHODAN. "How can you challenge a perfect, immortal machine?"

[Segev]

Black humor, and total irreverence. Violence is casual and funny.

The key is to be fun about it. For your in-group, at least. Belkar is actually a reasonable inspiration, especially once he figures out that working with the party is good for him.

As somebody who is chaotic and evil, you have no inhibitions save your own desires. However, you can also be a slave to those same desires if you're not careful. It doesn't mean you can't have long term plans, and want to keep allies around for those plans. But even better if you can find a reason why you like the other PCs and actively don't want to hurt them. You'd rather hurt others for hurting them.

Small bits of advice... watch Little Shop of Horrors and Addams Family. While the latter isn't always evil or chaotic, the flavor of humor will serve you well. Make a game out of seeing how far you can push things without going over the line that makes it end in violence; some of the best CE entertainment value comes from dancing on the other side of the etiquette lines that more lawful people are constrained by, or by making it a game of chicken with the good types to see how much collateral damage they're willing to accept, without you ever actually having to draw blood.

Be rude and blunt when others have to be polite, and make them risk breaking their own politeness to call you out, because you're pushing it juuuust far enough. Imply hostage situations; you don't need to even do anything about it, just imply it. Make the goody two-shoes on edge about what you MIGHT do, what you COULD do...and keep the person-shaped objects you're implying are your hostages in the dark. If the good guys start something, well, who knows what might happen?

And remember Belkar with the lawyers who were serving him cease and desist orders. "Hm, yes. This all seems in order. ...oh, wait. There's one flaw in this." "What? No! What is it!" "I'm chaotic."

[Magicspook]

1). Using Suggestion/Command (or similar spell, or even outright persuasion) - to convince a religious character to denounce/desecrate/defile their god/place/item of worship. Maybe a quest giver desperately wants me to save their husband? ''Well I could iiiiffffff you spit on your holy symbol'' -- I love this, as to me it really shows the 'evil' of the character, yet it's only a fairly small act.

2). Using illusion magic of some description for nasty pranks. So, hmm, I don't know, thinking on the spot here:
- Sleight of hand swap the innkeepers pen for my dagger.
- cast some illusion on the dagger to make it look like the original pen.
- innkeeper goes to write something - then he's going ''argh my hand!!!!''
- chaotic evil character is laughing their face off (or secretly laughing their face off perhaps).

Ok, admittedly that's a bit long winded, and that's a lot to go unnoticed. But I like the 'idea' - Again, it's a relatively small act that is generally both chaotic and evil in nature. However this does lead me back to my first point right at the top, why would my character do this? The only reason is surely they'd think it's funny? Is that a reason? Isn't that random/'chaotic stupid'?


Yeah, I'd say that those examples you gave definitely fall into chaotic stupid and personally, I'd hate playing with someone who pulls that sort of stuff. But I'm not at your table, maybe your table-mates think differently. As a general advice I'd say when you are about to do something 'evil or chaotic', think beforehand about why you lr character would do it. If the answer is 'because he would think it is funny' or 'because he is evil', *don't do it*.

A lot of the difference between fun and stupid is in the way you roleplay it, by the way; it is not just the act itself. A good roleplayer can get away with manymore shenanigans simply because the other players don't get bored of their antics as fast. Which brings me to my second and third tips:
Try to involve the other players in your schemes and never pull any of your shenanigans on other players. The former because then it won't feel like you are just selfishly eating up screen time for yourself, but actually enriching the game for the other players as well. The latter because if the players have had enough of your ****, the mood at the table can get real sour.

[Witty Username]

I would recommend making short-term, self-serving character goals as a framework for your behavior and when you see a chance to advance it take it. I will give your actions some predictability so other players can get a sense for warning signs for your evil acts and it will make it look less like you are just trying to get a rise out of people. Also, don't be afraid to "Every once in a while, declare peace. It confuses the hell out of your enemies." "Good" behavior isn't necessarily out of character if it either doesn't inconvenience you or actively benefits you.

I am working on a RP project of a high Reputation chaotic evil character, effectively so far a mercenary that works for money but at the end of the day likes killing things and looking cool while doing it. So he is polite in conversation and even willing to work for free if it means killing. Self-preservation dictates bandits are better to kill cause they are less likely to bring the town guard on his head.

What do you imagine as how your character is seen by others? that is a good question to keep in mind when picking actions for your character.

[rel]

Does anybody have any 'small' bits of advice? Little anecdotes perhaps? Things they've done that have been evil (preferably chaotic) and exciting, but not detrimental to the game, or 'stupid'? The last thing I want to do is annoy the other players or the DM.

How did your very evil character treat 'the quest giver'?
How did they go about general social interactions? Shopping, drinking at the tavern, etc.
How did they deal with confrontation?
What's the most evil thing they've done that everybody at your table was cool with?
What are some little 'everyday' examples of evil/chaos?

Etc. Etc. :)


Alright, so you say you have the basics down, let's get into specifics.

Quest givers probably have something you want (even if its just the location of the next loot filled ruin to loot) so you can't flat out dismiss them.

Exactly how you behave depends on how desperate and powerful they are, whether you will work with them again and how much you want their reward.

Rich and powerful guild leader wants an errand run at a good price? Be polite and don't antagonise him. You're evil not suicidal.

Poor peasants you'll never see again need help with kobolds you don't care about? Now is the time to crank up the dickery.

A few suggestions
-gouge them on price
-get them to give you some reward even if you fail or a fee upfront
-be rude in little ways; swipe their coffee, mock them for getting into the mess they're in
-be rude in big ways; dump the corpse of the monster they wanted killed on their desk, catch them at an awkward time to get clarification or report success or failure.

The end result should be that if everyone wants to do the thing you still do the thing.

hanging about town is generally handled the same way for most people regardless of alignment. Don't poop where you sleep. Read the vibe of a place, figure out what you can get away with and do that.

-you probably don't answer a cry for help from a dark ally
-if someone accosts you and there aren't any witnesses you aren't likely to show mercy
-no money to the beggar (or maybe loudly and obviously give too much so the thugs a door over rough him up.)
-people seem unhappy try and get a mob to form


Dealing with confrontation again, depends who's confronting you. But also really depends on the character. Sure if the royal guard of better-than-you have shown up everyone has to play nice.
but if a powerless peasant is causing trouble you can get creative with your responses. It doesn't have to be a straight up stabbing.

everyday evil
warlocks get a familiar. you can be monstrously mean to one of those and no one will care.

be miserly with the small stuff. Take prestidigitation and clean yourself (and only yourself) off whenever the party gets covered in mud.

invent nicknames for NPC's you can safely torment

play up your weaknesses as an excuse to get out of doing work;
"I am but a feeble warlock one of you strong fighter types will have to try forcing open that door."
"You know how I am with NPC's. I shouldn't go to the meeting, I'll be in the tavern"

Final note
keep your motivations secret and don't explain yourself. If people don't know why you are doing things you immediately appear more chaotic.

[Red Fel]

Final note
keep your motivations secret and don't explain yourself. If people don't know why you are doing things you immediately appear more chaotic.

I'm actually going to disagree with this. Here's why.

If the party doesn't know you're Evil, then keeping your motivations and goals a secret will eventually become a betrayal when those come out. The party won't like that. Betrayals sting.

If the party does know you're Evil, having motivations they understand is to your benefit. It makes you sympathetic, or at the very least a known quantity. Most parties are going to be wary of an Evil character, particularly a CE character. This is moreso when they don't know what makes your character tick. But if they do know your motivations, even if they don't fully understand them, you become someone they can deal with. Someone they can at least trust to follow whatever goals or drives you've established.

What you want, as the player of an Evil character generally (and a CE one specifically), is for the party to accept and support - or at least tolerate - your character and his actions. But that requires an understanding between the PCs, and that understanding won't happen where you're keeping aces hidden up your sleeve.

[BloodOgre]

There is an art to playing an evil character. Some people do not get that. Heck, some people think that being neutral allows them to do chaotic evil things with no consequences.

For me, the art of playing an evil character, chaotic or otherwise, is in taking advantage of situations as they arise, and manipulating others (PCs or NPCs) into creating those situations, especially when they would be otherwise opposed to doing what you want. In general, I have a goal, and the PCs work for me, they just don't know it. They are tools, just like a set of lockpicks, but you manipulate them with words rather than your fingers.

Even evil has a purpose.

[Segev]

Perhaps the most successfully villainous character I've ever played was in an Exalted game. He wasn't, ironically, all that evil by most criteria, but as a loyal Green Sun Prince, he was still pretty wicked just due to his goals and services to his masters. Not quite a punch-clock villain, but he did come off a bit as a cross between a true believer and "just doing his job."

And his job was to corrupt the other PCs into the service of the Yozi. His approach was to play up his genuinely helpful nature, to be legitimately friendly to them, and to pursue his more noble instincts and help out the world around him and the party. And just offer pragmatic solutions to problems the other PCs were having. Not even the usual "if you kill him, it'll be easier" sort of obviously evil pragmatism. But just pointing out all the options available, and emphasizing how wicked some of them were despite the fact that they're expedient and the surest way, he was outvoted by the party when he pushed for lighter touches, safer methods (for bystanders), or the like. And half the time, I'm pretty sure he was being successfully corruptive just because the PCs were not coming up with the more pragmatic solutions on their own.

The best one he managed was when the sorcerer-engineer in the party wanted a particular kind of magical castle, called a Factory-Cathedral. Or at least the next best thing to one (I forget what the step down was called). Being tied to the Yozis (ancient bound primordial beings that live in Hell and want out to take over Creation), he was able to speak to his boss and find "some rumors" about one that might be available for the taking...in Hell. Of course, the actual setup was that the thing was being arranged to be given to him so he would find reason to dwell in Hell much of the time, but there also was some legitimate problems its current demonic caretaker was facing.

So you can play evil while being genuinely friendly and helpful. Sometimes it's about just the options you present.

But usually, one plays Chaotic Evil to BE the poisonous friend. The one who will cut the gordian knot and solve the problem that had gotten to complicated to solve "nicely."