Hey all,

I've discovered, unfortunately, that while I feel competent and believable in my perfomances of NPCs (including friendly and unfriendly ones), I don't have much experience performing as a straight up villain in the heat of the moment. Most enemies my players have faced have been beastial or monstrous in nature, making for little dialogue, but now they are facing a recurring enemy who is one of the main antagonists of the story. We ended our last session mid combat with him and I realized I'm not very good at giving him dialogue which feels imposing and believable. Instead, I get a bit nervous, and he says things like "this is going even buh-better than... I ex-could have hoped!" because I am a bit clueless on improving a bad guy.

What makes it a bit tricky as well, is this character is kind of meant to be a bit cringey, or at least rather petulant. Think Anakin Skywalker, the young man (maybe only 18 years old) who's tapped into an evil source of power and is now living out his power fantasies and preparing the way for his dark patron. He's kind of meant to seem like the kid who's gotten in over his head, but at the same time, it's lame if he doesn't at least have a couple good lines or interactions. I could of course "pre-write" some, and I feel competent in my ability to do so, but it's the in the moment, on the fly dialogue in the heat of battle which leaves me stuttering and stumbling.

Does anyone have any advice and/or resources I can look at? Most stuff I find online just gives tips for making good backstories or not letting them die too early in battle, or for a player to be an evil character. Very little seems tailored for the DM who needs to suddenly give a villainous speech on the fly.

Thanks all

You could try actually playing up the awkwardness a little bit, which would make for some fun, though it also might detract from your villain's villanousness. I'm largely an improvisational DM, so I come up with most dialogue on the fly, but I do sometimes pre-write monologues. Also, I've found that having your villains talk slowly both gives them a sort of ponderous, superior feel while also giving you time to think about dialogue.

In general, though, the best thing to do to get better at villain dialogue is to consume villain dialogue. I watch a whole lot of Dimension 20 clips, and Brennan Lee Mulligan is incredibly good at villainous dialogue. I certainly wouldn't say that you ought to copy him, but simply consuming material will end up influencing your own capabilities.

I like to think what the villain wants, get in their head and use that to decide how you portray them. So as a DM of CoS I imagine what strahd wants, how he’s trying to achieve it e.g. 

- strahd is a prisoner

- strahd is timeless and puts plans into action that might take years 

- strahd is looking for diversion from the players 

so strahd is smart, cunning and looking to play cat and mouse with the party. I then play that up when role playing. I actually struggle more with NPCs, they are more likely throw away characters or quest givers etc so beyond being a plot tool it’s hard to play them.

I'm not great at it myself, but I've found it helps me to practice a little bit in advance, by finding a similar character in a film or TV show and watching a couple of scenes where they get a decent speech or monologue.  Then, I'd pick one out, repeat it a couple of times "in character" and start adding onto it, making up new details or branching out into a second topic, while keeping the character's original "feel."  

I suggest three simple steps:

1. "I'm right! How do you not see that??" - When you are playing the BBEG, do not think of yourself as the bad guy. You're not the bad guy! You're the one person who sees what must be done and who has the courage to do it! You're not evil. What does "evil" even mean anyway? Good and evil are just matters of perspective. Window dressing. You may get angry with the players, but that anger is based in frustration. You're certain that if they would just put down their weapons for two g*dd*mn minutes and just LISTEN, that they would see that you're right, and it's everyone else who is wrong. You are the one trying to save the world! To you, that's obvious. And it blows your mind that everyone else doesn't see that! Granted, your methods may seem a little... messy. But the world is a messy place. If you don't have the stomach to do what must be done then you shouldn't've gotten into the "world saving" business to begin with!

2. Gul Dukat.  The greatest antagonist on any screen, big or small, in the last 50 years has been Gul Dukat in Star Trek: Deep Space 9.  Go watch it. If not entire story arcs, at least watch highlight videos on YouTube of Gul Dukat. He's such a good antagonist that the U.S. Army War College in Pennsylvania once offered a course in counter-insurgency titled, "Gul Dukat." That's how thoroughly amazing that character is, and actor Marc Alaimo gave that character such incredible warmth, and intelligence, and ... dare I say it ... humanity! And he has some of the greatest villain quotes ever! -- "A true victory is to make your enemy see they were wrong to oppose you in the first place. To force them to acknowledge your greatness." -- Study Dukat. Be Dukat!

3. Patience.  Sometimes, the scariest thing a villain can say is nothing. Be patient. Don't feel the need to respond to every question or every taunt from the characters. Let a simple pause be your way of telling them that their questions are beneath you - that THEY are beneath you. Let your silence tell them that they don't deserve an answer, and even you gave them an answer, they probably wouldn't be able to comprehend it anyhow. A simple pause can have a powerful effect. Someone who is angry and violent expects (or even hopes) to get anger and violence as a response, because that response (in their mind) justifies their initial violence. But having the presence of mind to simply pause before responding to the words or actions of the characters, will show the players that your villain is not just a bag of Hit Points and XP. This villain thinks things over. This villain has patience. As Gul Dukat said, "Everything I have lost I will regain. It's only a matter of time." 

The scariest villains are not the over-the-top screaming monsters. Those are obvious. The scariest monsters are the ones who look nice and friendly, and who make a good point, "from a certain point of view." Besides Gul Dukat there's also a movie called "Mr. Brooks" from 2007 in which Kevin Costner plays a serial killer who's trying to overcome his addiction to killing people. THAT'S a scary monster! A good villain only destroys the party as a last resort. First, they will try to recruit the party. If you've written a good villain, at least a few party members should be honestly swayed by at least some of the arguments the villain makes. 

All villains are the heroes of their own story. As a result, when RPing a villain, playing them 'straight' rather than as a cartoon or otherwise will lend them more weight.

Even modern day villains are speaking a kernel of truth. For example, the UK's most fringe political parties win votes, not because their cause is considered 'good' but because at the core of their argument is something speaking to a truth. The UK leaving the EU for example happened because there are places of high EU investment where employment opportunities and wealth inequality have consistently gotten worse, while simultaneously seeing an increase in foreign workers...see the Welsh Valleys for a strong example of this. To those on the 'leave' side of the argument immigration spoke to the fear of those who saw an increase in migrant workers and equated that with the decline in jobs (as opposed to lack of investment in infrastructure and communities). This is where the seeds of extremism start. 

Taking the issue of extremism, many teachers these days confront the fact that extremist views begin small. Certain well known misogynists have become popular on social media because one of the (incorrectly concluded) opinions from discussions of toxic masculinity  has been that men = bad. In fact if one looks around at the media you don't have to go very far to see this narrative. Men are painted in the eyes of the impressionable as toxic, abusers, misogynists, and outright untrustworthy. Most reasonable people will acknowledge that the discussion isn't about all men rather the culture that allows such men to develop. However, the vulnerable male who maybe is finding it difficult to secure work, or make their way in the world is likely to be looking for a reason the world is so unfair to them. Enter a true villain (I'd rather not use their name), who provides them the reason they can't secure work...but hurling unwarranted venom and hatred at everyone who isn't the traditional toxic avatar of masculinity. As such by amplifying the reasonable view, cultures and societies drive the vulnerable into becoming the acolytes of the villains and actively fuelling the growth of said culture.

Evil...all evil breeds off of two things. First a seed of truth. Second a fear, however irrational.  When exploited by someone who either truly believes, or lusts after power at all costs...real evil develops. 

Going back to your original post then, if your villain is meant to be a little cringey what you've got is a cartoon. In which case any cartoon villain dialogue will suffice. If you want something with a little more weight they simply need to be more human. So you need to answer the question: why? Why is the villain doing what they are doing? Season Six of Buffy the Vampire Slayer was great at this life and it's challenges became the big bad. For the first time ever you had complexity. In the Pale Moonlight (Star Trek: DS9 episode) is also amazing at this. Cast in any sensible light, the protagonist, Ben Sisko, in undoubtedly the villain of the piece. For The Uniform (Again a DS9 episode) has Sisko recognising how the enemy believes themselves to be the hero. They are masterclasses in how to write good characters who, when seen from different perspectives, could be hero or villain.

It all depends on what you want from your villains.

There is nothing wrong with having cartoon villains. Star Wars media has been chock full of them...there hasn't been a single realistic villain in the bunch. It hasn't dented the franchise's popularity. And if you've meant your villain to be cringey, then there's no reason not to go that direction. If you want to inject a real sense of fear or a more realistic villain, I'd suggest considering having the clown being the figurehead. Essentially the figure behind the curtain points them in a direction and let's them go at it.

Finally, the only thing scarier than the real villain who believes their goals are right, is the true agent of chaos. Make no mistake these people do exist though are exceptionally rare...usually having some form of psychological illness such as Charles Bronson. Heath Ledger played this spectacularly in the Dark Knight film. Ledger's Joker was the perfect encapsulation of the chaotic personality with a psychological illness. The fear here often arising from our inability to conceive of the why or rationale behind actions. 

The real answer comes back though to what type of villain you wish to portray. And again, there's nothing wrong with the simple BBEG. Evil for evil's sake is entirely valid even if it becomes cartoonlike.

So, I think there's something to be said for straightforward villains if you approach them from the right perspective. Namely: what kind of problem does this villain pose for the heroes? "Hero of their own story" villains make the heroes examine their own assumptions about what's right, and that's valuable. But I don't think it's the only secret to villainy. A villain who's not just a physical obstacle can pose an interesting mental challenge (maybe they're an intelligent strategist, or obsessed with puzzles, or just have a weakness that's hard to discover or exploit). Or they can play to a character's insecurities. If you've got a Warlock with an evil patron, give them a villain with a similar or same patron who's gone fully off the deep end, or maybe an overzealous Cleric who thinks they're an abomination. Maybe both at different points. Is the Cleric right? Probably not, but now they have to ask the question. And none of this requires much depth to either the rival Warlock or the Cleric.

That's not to say don't think the villain through as having their own motivations. But they do have a practical role to serve in the plot, and especially if you have limited time and space to characterize them, that role supersedes their own characterization. You can have a very clear sense that the shopkeep the players are haggling with is trying to feed his sick mother, or the shops across the way have even higher prices and he thinks he's already doing them a favor, or he thinks he's entitled to set whatever price he likes, or he's never been challenged like this, or he really is just that greedy. But all that reaches the players 90% of the time, and all you need to come up with if this scene hits you unexpectedly, is that he's stubborn about his prices. The giant spider in the cave dungeon might be trying to feed her young but has been cut off from food by the goblins higher in the cave, so the heavily armed players she wouldn't otherwise mess with are the best shot she's had in a week. That's actually good because now maybe she'll decide discretion is the better part of valor and back off if she's injured, but mostly the players will only care that you've put a monster in front of them. The Devil who's been manipulating the adventure might be a delightfully insidious schemer whose plans to bring the kingdom down from the inside have wheels within wheels and who gets a ton of memorably evil one-liners... but she's ultimately only doing it because Devils are gonna do what Devils are gonna do. Otherwise they wouldn't be Devils. (Not that you couldn't flesh her out too. Maybe she's been an overlooked functionary in the Nine Hells and this is her first big chance to rake in some souls and climb the ladder. This assignment is more freedom than she's ever had and she's having a blast making the plan way more complicated than it needs to be. Or she's done this a thousand times over the history of the world and has an almost bored, "seen-it-all" kind of attitude. But it's all predicated on Devils just being evil because that's what they're in the game to do.)

All of that's very top-level, though, and not really related to playing a villain. That really does depend on what kind of villain you have.

The villain you're describing sounds like there are a few ways you could approach him:

• He could be relatable. Maybe not "relatable" in that you sympathize with him. But he's awkward. He's frustrated. He can't think of clever quips. He's a monstrous villain with disconcertingly normal problems, even as he's still dangerous. That's going to throw the players, and they're going to remember it because it's not like other villains they've encountered in other media.
• He could be scary. But what's scary is that someone so childish is wielding such power. So, you want to emphasize that he's... kind of petty, maybe. Now, for this kind of character, it's hard to figure out what to actually make him say, because he could easily become laughable if he's really acting childish. But I think I'd play up that when he thinks he's winning, he's having fun. It's a game to him. When he thinks he's losing, he's confused because he didn't realize anyone could challenge him or that his actions might have consequences.
• This one might be hard to do for a number of reasons, but you could also show the pettiness by making him be casually hurtful. Like, if you know what kinds of taunts would get under the characters' skins (the characters, not the players; this is living a little dangerous boundary-wise, so I'd be careful about it), maybe he needles them in a way that punctuates a certain mean-spiritedness.
• He could just be... annoying. Like, if his lines are coming out poorly, lean into it. Give him such an inflated opinion of himself that the players will be thrilled to finish him off.
• I don't know if this works, but you could keep him much more quiet and mysterious, and only make it clearer from later context what's been going through his head. In some ways, that's how Darth Vader was. He was always a sad, broken kid lashing out at the world, but before the Prequels (or maybe Return of the Jedi to some extent), we only saw this mysterious seven-foot-tall juggernaut with strange powers and a cool voice.

Part of it is: As you say, you haven't played a character like this before. Getting a certain cadence or confidence down may just take time and practice for you. Imitating some fictional villains you like is a good suggestion and might help you prepare.

A lot of ink or rather 1s and 0s have spilled on this topic, much of it very good advice so I'll keep this succinct. A good villain:

1. Has a motivation opposed to that of the characters. The villain wants something very badly and is having trouble getting it. What ever it is, the PCs need to want the opposite.

2. Is flawed. The reason they want whatever it is should be anchored in a flaw or other weakness the villain has. This one can really help with the role play of a villain, a greedy villain will become very defensive when the PCs damage their material wealth, steal from them ect. (Sheriff of Notingham), an egotistical villain might become enraged when the PCs outwit them, "Inconceivable!" (Vizzini from the Princess Bride). For me this is the fun part, roleplaying the villains flaws both engages the PCs and gives them a vital clue as to how the villain might be defeated. :)

Now in addition to 1,2 a great villian:

3. Takes something from the PCs that they love or value. They kill a beloved NPC, or even a PC*, burn the PCs home village to the ground, or better yet, breaks the PCs hearts.

4. Sort of has a point (Gul Dukat, Thanos ect.). I would say this is entering into advanced villany. A thoughtful villain will argue with the PCs, pity them that don't see the bigger picture, try to recruit them ect. They'll do all of these things before resorting to #3 in an epic backstab/show of force. If you want to play this sort of villain they may start as an NPC quest giver. This is also something I would reserve for the BBEG, relatively minor villains don't need to be this sophisticated.

Now lets tie all this together for some roleplay advice which is what you actually asked about. You mentioned you were comfortable with playing NPCs so I would start there. At the simplest level a villain is an NPC with motives that oppose those of the PCs, so start there. Sounds like you have a villain with interesting/charmingly annoying quirks and mannerisms. To take it to the next level lean into their flaw(s) and how it connects to what they want. What the villain says should frequently, if not always reference those things in some way. Finally to tie #4 or #3 into things you might consider the patron of you villain reaching out to the PCs with an offer of some sort if thats appropriate.

Happy Gaming!

*Make sure your players are ok with PC death and never railroad this. If it happens its great motivation for hating a villain.

Wow, this has been an incredibly helpful outpouring of in depth, detailed advice - Thank you guys so much! In particular I love the Star Trek/Gul Dukat reference idea. DS9 is one of my favorite shows and it's been too long since I've watched and really studied the characters again. I'll definitely need to do this.

There's too much excellent responses to reply to everything directly, but I'll summarize my thoughts on what's been suggested. For ease of reading, I'll refer to the villain I've been discussing as Q, a warlock of a greater power.

As you've suggested, I think it's a great idea to lean more into the awkwardness of Q. He IS a kid, he DOES get frustrated when the PCs don't take him seriously. I've taken the idea that, much like myself preparing lines of dialogue for him to say to each of them, that he actually did the same thing, and memorized "cool" lines and comments to say to each of them. One player even witnessed him mumbling to himself before responding a player, which was him practicing what he was about to say (though the player didn't roll a high enough insight for me to directly explain that to them). He is petty, he feels he is owed this power, and he's having fun using it, and he's also in way over his head and doesn't really understand there can be consequences yet. In fact, in the combat session (which is still ongoing), he has teamed up with a group of bandits to set this trap for the players, and the players even drew it out of the bandit leader: "Why are you working with this guy?" and even got the bandit captain to refer to Q as a "petulant boy," hopefully demonstrating that even other, more experienced antagonists don't necessarily like or respect the guy, even if he does have insane powers. 

During the combat, a hostage situation of some NPCs the characters had been escorting to town (a choice made on their own volition with no prompting from me) led to one player making some bad decisions, which caused one of the NPCs to be killed by the bandits. While maybe not directly at the hand of Q, the trap was his design (which he did boast about), and that moment especially drove the players to even more firmly want him dead.

Q's past experiences of being a slave to a wealthy, abusive family, then sold on the markets, before escaping and working for a mercenary group have given him a twisted viewpoint - he detests the idea of being a servant or slave to anyone, and wishes to be free. The patron (BBEG) sensed this in him, and began tempting him with power and purpose, to use him as a vessel to prepare his arrival. Q believes that becoming a 'herald' of this dark patron has given him powers and the freedom he's been owed, in exchange for some work, not realizing the irony and sad truth that he's just inadvertently resigned himself to being a slave yet again, to perhaps the worst master of all. I fully expect, and even intend for him to be defeated and/or killed by the end of this combat, and to be spirited away by his patron (the BBEG) after his death, to then later show up again as essentially a puppeted husk, more powerful, but with little of his mind or personality left intact. Perhaps his tale of temptation, corruption, and never having truly escaped slavery will make for a compelling arc. I'd really like it to come through that even though he's a rotten guy and does horrible things, he's really little more than a sad, embittered young man who got in way over his head. I don't know if redemption is really on the table for him, that'll be mostly up to the players I think, but I've laid some seeds (including talking with a former friend of his at the mercenary group) who actually cared a lot about him and is worried about him.

I really appreciate the advice given here and I'm going to be copying it all down into a document to refer to multiple times, as it's just been really good character writing material and will come in handy. If all goes well, then you guys may even have an opportunity to see this character - and the adventure he's a part of - kick started into something more tangible.

So, imma say only this bit of advice:

You said he is a little like Pre Darth Anakin. Go watch episode 2 and 3 then. With remote in hand or finger in the slider and pay attention to his posture, his expressions, his cadence of speech.

then do that.

the rest of it is fine. So you flub a line — that most likely isn’t going to be what is remembered. Nobody ever remembers what the great wazoo says, they remember how he says it: with a whistling sibilants and a lot of cranky old man with a bad cold.

even if his attitude is a certain way, make how he speaks something memorable and he will always be remembered. I stutter in things a lot, because I am trying to think of likely actions and outcomes, and so I might effect it for my affect.

I mean, my experience says PC’s remember what they did, and the weird stuff about the villain, and that’s about it unless the whole table is laughing at something.