Making Evil Characters: A Guide to Crafting Anti-Heroes in Dungeons and Dragons

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Introduction: Crafting Anti-Heroes in Dungeons and Dragons

We love a good villain. We’ve all tried the evil playthrough in our favourite RPG video games, and I love playing evil characters in my buddies Dungeons and Dragons campaigns. But most Dungeon Masters have an aversion to evil characters, myself included, because simply put, they’re just not done right.

Everybody is capable of making an evil character, and being evil isn’t inherently a bad thing, but most people hate playing with an evil character because tabletop gaming is all about fun roleplay as a group, and the conventional evil character (a traumatized, brooding psychopath with an edgy backstory) ruins that fun. I’ve witnessed the breakdown of several campaigns, and friend groups, because of growing resentment between players due to poorly executed characters, good and evil alike.

Perhaps a better term for what I am discussing is an anti-hero, and speaking personally, roleplaying anti-heroes has created some of the greatest moments and stories in my decade of playing tabletop games. In my opinion, it’s a true shame that roleplaying evil is so taboo due to horror stories amongst the community. But when done right, an evil character provides captivating conflict, fulfilling roleplay, and introduces some of the most impactful storytelling I can imagine. So how do you make an evil character correctly?

I’d like to offer my tips for crafting effective anti-heroes for your next Dungeons and Dragons session.

Trust and Predictability in Anti-Heroes

Tabletop gaming’s most distinguishing aspect is improvisational roleplay, and no other media allows for so much player freedom; video games get close, especially my RPG personal favourites Fallout: New Vegas and Baldur’s Gate 3, but they fall short of tabletop gaming. Tabletop systems like Dungeons and Dragons allow a group of friends to tell some of the most personal and meaningful stories imaginable, with the only limitations being scheduling, the bane of all tabletop groups, and competence.

That competence is the bedrock of roleplay. Prior to any gameplay, the group forms an unspoken agreement on their rules and methods of roleplay. This is a process unique to each group, but one of the most critical guidelines to effective roleplay is to anticipate your characters.

In traditional acting, the ability to improvise takes a lot of group practice. When actors are improvising a sketch, they know each other’s strengths and what they’ll react to best, and they’ll intentionally lean into each other’s strengths to let everyone shine in the spotlight. Once given a prompt, they bounce off one another by anticipating how the others react, letting each actor contribute to the story’s conflict and grow their character in order to create a satisfying conclusion. This skill requires teamwork, mutual insight, good judgment of character, but most critically, a consent to being vulnerable. Improvisational acting especially is vulnerable, and when you fail to anticipate how your friend will react, it damages both your self-confidence and your trust in your friends. This translates one-to-one with roleplaying in Dungeons and Dragons.

An effective character is predictable, meaning their actions are determined by their convictions, and here we find the biggest difference between good and evil characters. A good-aligned character’s actions benefit society, and their convictions are socially accepted, meaning the group can understand and determine how their characters feel about them easily, which is conducive to roleplay. An evil-aligned character’s actions harm society, which is difficult to rationalize and understand, diminishing our ability to react; we’ve effectively shut down the other player's chance to share our spotlight because they can’t understand how to, which leads to a failure in roleplay and erosion of trust. This is why playing evil characters is taboo; most evil character actions cannot be forgiven because they also exhibit socially reprehensible traits; there is no means to rationalize or forgive their evil.

This is why evil characters need to be so much more developed, which we’ll discuss further below; their actions must be evil, but their convictions must be noble. Without morally acceptable convictions, there is no gray area to allow a good-aligned party to work with an evil person, because you’re no longer an anti-hero if you aren’t noble in your evil, you’re now just a villain.

Understanding Motives: The Roots of the Anti-Heroes Evil

No one believes they are a villain. People commit immoral actions for many reasons, but nobody does so simply because they can; all people who commit evil do so with intentions that are, to them at least, justifiable. In storytelling, our characters should never commit immoral actions without an understandable reason, or else we alienate the character, and ensure our group fails to meaningfully roleplay with them. In other words, our anti-hero’s actions must stem from good intentions and noble beliefs.

Modern ethics philosophy doesn’t have an agreed shared definition of moral evil, but for the purposes of discussion, I’ll use the 4 Roots of Evil as popularized by Lars Svendsen’s A Philosophy of Evil (2010) to attribute and analyze how our character can commit evil:

Demonic/Pleasurable Evil - Evil committed for the sake of being evil, most often for sadistic pleasure. We often view this evil as inexcusable, but examples of demonic evil can captivate our morbid curiosity; think of Ted Bundy, Jack the Ripper, Albert Fish, etc.
Instrumental Evil - Evil committed as an instrument or tool to achieve an end. Generally, the evil is used to maintain power or gain control through fear of repercussion, such as in organized crime, torture, dictatorships, etc.
Idealistic Evil - Evil committed out of a perceived moral duty, where the moral good of the results is argued to outweigh the moral evil of the action. Arguably the most justifiable form of evil, we often see this evil explored in utilitarian arguments for sacrificing a few to save the many, such as the Trolley Problem, eugenics, the War on Drugs, etc.
Banal/Foolish Evil - Evil attributed to human incompetence or willing ignorance to one’s consequences. The term was popularized by Hannah Arendt’s Eichmann in Jerusalem: A Report on the Banality of Evil (1963) to describe willing perpetrators of the Holocaust who saw their actions as outside their control or forced upon them, but many forms of banal evil exist in daily life. Arguably the most aggravating form of evil, it was one factor in the creation of Hanlon’s Razor, “Never attribute to malice that which is adequately explained by stupidity”. Examples include drunk driving, Chernobyl’s meltdown, the Milgram experiment, etc.

In order to create an anti-hero that we can rationalize, understand, and possibly even sympathize with, we must avoid use of demonic and banal evil, and instead explore instrumental or idealistic evil. It is nearly impossible to rationalize sadistic torture/murder, and rationalizing an irrational character is an exercise in futility, but evil as a tool in the pursuit of justifiable needs, or a skewed but noble pursuit of greater good can sometimes be more compelling than a morally good character.

Thanos from Marvel’s Infinity Saga is an excellent case study, because we can understand why he thinks destroying half of the universe is the only way to ensure continued existence. He isn’t a comical caricature with a twirling mustache, but a traumatized sole survivor who witnessed the fall of his homeworld. He makes sensible, compelling arguments for why it occurred, and how he thinks he can prevent it. His evil is idealistic, he does what he does because of a greater duty he believes allows him to commit such great evil; we sympathize with him, we can respect his conviction, and even though he is wrong, we construe him as a tragic character, making his story all the more impactful.

Examples of D&D Anti-Heroes: Balancing Darkness and Light

Now that we understand how to create sympathetic immoral characters, this is where the background, personality traits, ideals, bonds, and flaws included in the Dungeons and Dragons character sheet can support our anti-hero. It’s easy to get carried away with evil, so by writing effective prompts for our character, we can ensure they only commit immoral actions when they deem it necessary, which helps us remain sympathetic.

Provided below are a few examples of strong anti-heroes, but ask yourself as you read these characters; why do some resonate with you more than others?

An organized crime family’s enforcer:

Background: Criminal. Joined an organized crime family at a young age, and climbed the ranks to be a respected member.
Personality Traits: I’m the first in the door, and the last one to leave. I’d rather die than be seen as weak.
Ideal: Never speak out against your superior; their word is law, and your life is theirs.
Bond: My chronically-ill mother relies on my income to survive.
Flaw: Words and diplomacy is for fools and the cowardly.

This character demonstrates an instrumental evil, where he uses threats and violence to achieve his needs, but he does it to protect his mother, a sympathetic goal. Likewise, his headstrong nature and intimidating presence allows him to be a party’s vanguard, and his flaw could challenge more diplomatic member’s of the party and lead to fun roleplay; a clever bard might use their weak appearance to feed into his superiority and manipulate him, for example.

A vindictive paladin fighting a holy crusade:

Background: Acolyte. Sought penance by pledging her wrath only be used against her Goddess’ enemies.
Personality Traits: My word is my bond, I shall never lie. My wrath is swift, fiends should be wise to draw its ire.
Ideal: It is the duty of the strong to defend the weak from the wicked.
Bond: An insult to my Goddess is an insult to me.
Flaw: The forces that threaten my city will show no mercy, and neither will I.

This character demonstrates an idealistic evil, and may even be seen as a hero by the party. Her vengeful and merciless nature ensures any enemy she faces will be dispatched without prejudice, and her traits make her a noble warrior. But her overzealous and blinding wrath could be misguided when dealing with surrendering foes, innocent collaborators, and non-participating bystanders who she perceives to be part of the enemy. As an example of a similar character from my past, after raiding an orc encampment, I argued for the murder of innocent orc children because they’ll one day grow up to be soldiers too. Am I still a hero, or have I crossed the line of moral duty?

A bard fighting corruption with corruption:

Background: Folk Hero. A tyrant rescinded an unpopular decree after I threatened to reveal his shameful secret.
Personality Traits: My confidence in my own abilities inspires those around me. There is no such thing as fair play when fighting injustice.
Ideal: Tyrants must not be allowed to oppress the people.
Bond: I protect those who cannot protect themselves.
Flaw: Secretly, I believe that things would be better if I were a tyrant lording over the land.

This character demonstrates an idealistic evil, but not an obvious one. They may be a diplomatic force against tyranny, but they themselves are not above corruption, and when nothing is off limits, where do you draw the line? This character has the potential to draw the party into a scheme so immoral, they may question if they themselves are becoming the tyrant they fight against. Most importantly, this character demonstrates that violence and overt immorality isn’t needed to commit evil, because in the real world, the most evil actions usually stem from the most noble intentions.

Guidelines for Crafting Respectful Anti-Heroes

Returning to our goal of creating compelling roleplay through our anti-hero, we should discuss the ways an anti-hero can respectfully create conflict.

Remember, the ultimate goal of playing Dungeons and Dragons is to have fun with friends. The fun of storytelling is drama, which revolves around the cycle of growth through both internal and character conflict. The struggle to adhere to one’s beliefs and morals is the fun of roleplaying, but if you don’t show growth through roleplay, your anti-hero risks being seen as too irredeemable to be taken seriously. Above all else, if the drama between characters is beginning to affect and harm the dynamic between you and your friends, you should never feel compelled to continue driving the nail deeper into the coffin. If a character is causing so much conflict in the party that you don’t know how to resolve it, it may be best to speak to your party about retiring the character; there’s no harm in admitting you were wrong, and oftentimes it’ll be for the better.

The following are tips and guidelines I personally keep in mind when roleplaying:

Respect people’s boundaries. This may seem like a no-brainer when playing with friends, but proactively asking the group about sensitive topics will help avoid unnecessarily upsetting players. Generally speaking, you should never approach sexual violence, domestic violence, and real-world prejudice, but some players may be upset with fantasy racism, xenophobia, infanticide, torture, etc. Each group is unique, and it will never hurt to ask what people consider off the table.
Never target the players, only the characters. What is considered immoral can be very opinionated and quickly become heated, and there’s times when a statement intended to provoke character conflict is misattributed as a personal attack of a player. While the hurt feelings are unintentional, it’s important to immediately address it, and if it can be assumed the same action will upset a player again, it is on you to stop such behaviour immediately. No amount of roleplay and “that’s what my character would do” justifies upsetting friends.
Say your character’s thought process out loud. Playing an anti-hero, especially an ambiguous one, can sometimes leave people uncertain of how to react. A good method to avoid misunderstanding is to say your character's thought process out loud, either as an in-character monologue, or out-of-character as a method to help guide fellow players.
Be willing to concede for the betterment of the party. In a group game like Dungeons and Dragons, if the entire party is in favour of a certain action, it can be more harmful than dramatic to oppose the idea. If your character would never agree to something the party wants, bring it up out-of-character to the party, and see if your character can talk the party into a compromise instead. You’d be surprised how willing the party is to offer suggestions as to how you can persuade their characters.
Be open to challenging character beliefs. One of the greatest tools an anti-hero has at their disposal is being able to point out the hypocrisy of a hero, and vice versa. Don’t be afraid to challenge a character’s morals (with approval from and respect for the player, of course) if you think it would be a good roleplay moment. Characters are meant to grow and change, and a hero falling to immorality is just as compelling as an anti-hero rising to morality.
Make sure you are having fun too. When playing an anti-hero, it’s not uncommon to have your character beliefs and your personal beliefs conflated by other players. If you feel like someone is judgemental of you personally, don’t be afraid to speak up and calmly explain you don’t appreciate being judged. Your fun is just as important as everyone else’s, and all of these rules go both directions.

Conclusion

This article only scratches the surface of creating anti-heroes and exploring evil in tabletop gaming, so if you try your hand at playing an anti-hero, I’d like to remind you that it is okay to make mistakes. Everything I’ve written above is my personal experience with character building after almost twelve years of playing tabletop games, and I still make mistakes. Like any skill, you will get better as you practice.

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