Taking 20 Podcast - Ep 268 - Should Villains Be Sympathetic

Episode Date: January 11, 2026

Is your campaign's "big bad" just evil, or is there a hero beneath the monster? This episode dives into the age-old debate for Dungeon Masters: how important is a sympathetic backstory for a villain, and whether you should include complex antagonists in your game   #rpg #ttrpg #dnd #pathfinder #gmtips #playertips #tabletop #roleplaying #villains Resources: Episode 180 - https://www.taking20podcast.com/e/ep-180-let-villains-be-villains/  Episode 235 - https://www.taking20podcast.com/e/ep-235-the-why-of-villains/  Episode 253 - https://www.taking20podcast.com/e/ep-253-recurring-villains/  Thor Skywalker - Why does everyone seem to love “Sympathetic Villains” - https://www.youtube.com/watch?v=VO2dBY8DPho  Buy Me a Coffee! - ko-fi.com/taking20podcast www.taking20podcast.com  Instagram - https://www.instagram.com/taking20podcast  Facebook - https://www.facebook.com/taking20podcast  Bluesky - https://bsky.app/profile/taking20podcast.bsky.social

This week on the Taking 20 podcast. In very few realistic portrayals of people, good or bad, are they one note, purely evil, purely altruistic, purely selfish, purely holy? Most of us are a mix of all of our good and bad traits that we are. Thank you for listening to the Taking 20 podcast, episode 268. Answering a listener question, do you need a sympathetic villain? I want to thank this week's sponsor, Clocks. I have a very good friend who's completely normal except he likes to eat clocks. Dinners with him are really time-consuming.

Happy New Year to everyone out there. I hope all of your 2026s are better than 2025 and are full of fun games and great stories with friends and acquaintances alike. Hey, we have a coffee, K-O-F-I.com slash Taking20 Podcast. New Year, new set of expenses I'm paying off with domain registrations hitting this week. If you enjoy the podcast and can spare a few copper pieces, I would be most appreciative. But if you can't, it's okay. Thank you very much for listening, and I hope you find the podcast entertaining and educational. This week's episode is from a question from Wes in Delaware.

He writes, hey, love the podcast. I'm designing the big, bad, evil guy for my campaign, how important is a sympathetic backstory for a villain, and how do you ensure the PCs feel justified in opposing them? I've talked about villains a lot in my five years of running the podcast. A casual search of my previous episodes show at least four of them focusing on villains, including something fairly on point back in episode 180, where I encourage DMs to let their villains be villains.

I'll include a link to that episode in the description, and if you're listening on YouTube, there should be a little card in the corner where you can listen to that episode as well. To summarize episode 180, I encourage GMs to let their villains just be the monsters they need them to be. I talked about the draw of a sympathetic villain, but how not every villain should be redeemable. For the record, I also talked a little bit about villains in episode 235, and recently with episode 253. I'll include links to those episodes in the description and little cards as well. You may be saying, Jeremy, that's a lot of villain talk. Aren't there other

topics you could cover? Well, yeah, and if you have ideas, I would love to hear from you what topics you'd like me to talk about. Message me on any of the social media, links in the description, or send me an email, Feedback at taking20podcast.com. But yes, I do talk a lot about villains. Why? Because the Big Bad in your campaign is one of the most important aspects of your game, possibly behind tone and setting.

The Big Bad is going to be a major motivating factor for your party's adventuring choices. Do they rest now or push on for more fight? Are the lives of the town folk, are their loved ones in danger? A campaign with a big bad that is a Cthulhu-esque world-ending creature from beyond the stars will feel very different from one where the corrupt vizier is poisoning the nobility against the king by sabotaging major decisions. Over the last, I'll say 25 years, I've noticed an increase in making villains more complex and sympathetic. Take Darth Vader, for example.

In episode four in Star Wars A New Hope, Vader is a terrifying, menacing, brutal enforcer of the Empire's goals. He is singularly focused on eliminating the Rebel Alliance. Three years later, in 1980, Vader was made a touch more complex by introducing the fact that he is Luke's father. Spoiler alert for a 45-year-old movie of Empire Strikes Back. In 1983's Return of the Jedi, the complexities really start to appear as he's torn between his loyalty to the emperor and moved by his son's attempt to redeem him. In the second trilogy, by the way, episodes 1 through 3, released from 1999 to 2005, Vader is shown to be a gifted but emotionally immature, uncontrolled.

Let's go with emotionally stunted young man who bristles at the rules of the Jedi order and just wants to throw off their limits and both express his power without restriction and probably bang Padme like a screen door and a tornado. I have been told by my wife that that example was probably inappropriate for a podcast. My apologies. I'm going to change it to... He wants to go at Padmeh hotter than two rats and a wool sock. Like two rabbits hopped up on espresso?

Take her to the Hawaii island of How Are You Wanna Licky? Or Kamana Wanna Laia? Give her her love pizza, extra pepperoni. Grind on it like a belt sander with a grudge. Hammer at it like a woodpecker on a light pole. Hi, editor Jeremy here. actually goes on for another four or five more inappropriate jokes, including my favorite involving the great phrase, baloney pony. But I'll stop it here for the sake of brevity and because of the

dirty looks I'm getting from my wife. In episodes one through three, it shows Vader as wanting to make a choice for the woman that he loves, rather than giving up a normal life to serve the Jedi. The emperor plays on this desire to tempt him to the dark side. That makes Vader a much more sympathetic villain than he was portrayed in the original trilogy and shows the tragic situations and decisions that led to him slaughtering dozens of younglings in cold blood. Does that make him a better big bad? Probably. There are arguments for and against making your villain sympathetic.

Let's start with the obvious. Sympathetic villains are more realistic in a lot of ways. In very few realistic portrayals of people, good or bad, are they one note? Purely evil, purely altruistic, purely selfish, purely holy. Most of us are a mix of all of our good and bad. traits that we are. I try to be accepting of everyone around me, regardless of who they are and what they believe, and I think that's a good trait. But by the same token, when I am tired or frustrated or in pain, I get pretty snippy and speak without thinking and can hurt others. I recognize my flaws,

and I'm working on them, but I do still have them. I say this because there are some people out there who I'm sure would consider me a villain in their story. Recently, villains are being written to be sympathetic. One of my favorite, by the way, was Eric Kilmonger from Black Panther. He wasn't raised in Wakanda and thus sees the world through a different lens. He sees the isolation of Wakanda and the hoarding of valuable resources as selfish and knows that oppressed people around the world could benefit from Wakanda in technology. Don't get me wrong.

I'm not saying he was doing the right thing. in the right way for the right reasons, but his position was understandable and thus made him a sympathetic villain. If we rewind the clock just a little bit, there's a term I've used previously on this podcast, cartoon villain. That terms become somewhat dated,

but it perfectly captures the black and white morality of like 80s and 90s animation of my youth. Back then, antagonists weren't written with the gray morality that's common in today's movies and stories in cartoons even. When you watched Venger or Cobra Commander, you weren't looking for a reason behind the wreckage that evil was just the point of their character.

By removing the tragic backstory, I mean, these cartoonist shows created a sense of pure looming stakes. The villains weren't victims of circumstance. They were personifications of greed and malice, providing a clear and unshakable objective for the heroes. Defeat this monster and is, organization to save the day.

Sympathetic villains make for great role-playing, though. I've used him as an example before, but consider Thanos's motivations in the MCU. He saw his planet suffer and starve due to overpopulation and sees the universe going down that same direction and thinks that he is fixing it all by cutting population in half. Or actually also in the comics, he's in love with Lady Death, who in the MCU was later played by Aubrey Plaza and Agatha all along, so I mean, if death looks like her, I'd probably fall in love too. Anyway, he wanted to get Lady Death's attention, and that was another reason for his killing half the universe. Was Thanos's plan flawed? Absolutely. You bet. Why half the population?

Why not only leave a fifth of the population, or a hundredth, or some other arbitrary fraction of living things alive? Why not double the universe's resources instead of cutting the population? in half or make living things able to survive on less resources. However, Thanos' backstory at least made his plan somewhat understandable from his skewed and flawed perspective. One of my favorite tropes in media, by the way, or gaming or whatever, is, how did the green goblin phrase it? We're not so different, you and I. I love stories where the hero and the villain face similar struggles, challenges, decisions to make, and the key difference would be how they reacted and the choices they made when the chip were down. Sorry to stick with the Marvel universe,

but Green Goblin and Peter Parker were both brilliant scientists who used their intellect to enhance their capabilities. Both were created by accident, both lead a double life, both discover that they have power over others. And the difference is that Norman Osborne believed that that power was a means of serving himself to get what he wanted, while Peter believed that with great power comes great responsibility to others. That kind of parallel makes it for great storytelling and a compelling villain. It's the old there but for grace go I. Here's the problem with compelling villains, with complex storytelling, sympathetic villains.

To explore these backstories, it takes the DM or storyteller a long time to fully flesh it out. With Thanos, we had, what, 22 movies to explore him? most of us, when we're running campaigns, don't want to take the time to properly document why a villain is who they are. And unless you're running a role play heavy campaign that's willing to take its time, a lot of players just will become bored with a slow reveal of the Big Bad's Pass to make them sympathetic. I've mentioned, by the way, I researched these topics as I'm writing because I believe good ideas come from multiple sources. I found a great video by a content producer named Thor Skywalker, and I want to quote him directly. We tend to like villains with a tragic backstory or understandable reasons for them to do the evil things they do,

because human beings prefer villains who are made not born. There's a comfort to villains who may be savable, solvable, or fixed. Something went wrong that we can understand. I'll include a link to his video in the description, and there'll be a card in the corner. But he's right. There's a comfort to the belief that no one is born evil, but they're a victim of their circumstances and choices. To see how this has changed over time,

look at the ways Wizards of the Coast and Paiso have changed the handling of ancestries and races. In AD&D, way back in the day, dark elves were described as sinister, cruel, and cunning, were willing to torture, maim, and kill in service to Lolf, their evil, fallen spider queen goddess. By 3.5, they were described simply as despised enemies, and by 5E, they were described as being intelligent and fiercely competitive, sometimes to the point of resorting to treachery and murder.

In the early days, Drow were a convenient enemy because they were uniformly, irredeemably evil with no cause or reason. Now there's a tendency to make the reader or the GM or the player understand why they are what they are. Similarly, in Pathfinder First Edition, goblins were just chaos incarnate, loving fire and destruction and sometimes killing themselves in the process, whereas now in 2E, they're a playable ancestry,

and ancestries aren't inherently evil anymore. Similarly, orcs and lizard folk, hobgoblins, and even undead can be PCs in a lot of game systems out there. Creatures that used to be one-trick evil ponies simply aren't anymore. The focus has changed to make evil a choice, not part of who they are. Overall, by the way, that gives PCs more options

to the types of characters they play, and I think that's rarely a bad thing. Generally, players have more fun when they can play the type of character they want to play. Especially on the PC side, by the way, it makes more great story that the half-orke saves the town who shunned her, or that a fragile piece has emerged between the hobgoblin kingdom under the mountain

and nearby hill dwarves. This introduction of more moral ambiguity allows for a wider variety of stories and mechanical separation of physical appearance and personality. To that end, I always like flipping the script if I'm going to go for a complex, sympathetic villain. If long-held ancestries that were considered evil can be good, why can't long-held ancestries that were considered good turn evil? Imagine an Azamar, a villain who is effectively half angel, destroying entire swaths of people

because they perceive their actions as evil and anathema to their God and their beliefs. I mean, wouldn't that make sense? In games where you think villain complexity and sympathy would make for a better game, consider turning the trope on its head, the silver dragon who's been driven to destruction by the flighty humans she's tried to assist for centuries, but the humans just seem to be bent on self-destruction anyway. So she's decided to purge the unworthy, carve out the corruption by violence,

doing a little evil to accomplish what she considers a greater good. If you do go down the road of sympathetic villains, there's one phrase I want you to keep in mind. Villains are the heroes of their own story. Osamandius from the Watchmen considered himself to be a hero by giving the U.S. and USSR a common enemy to avoid war. He believed that he had to kill millions to save billions. Magneto believed he would save all mutants by killing the humans who had inevitably tried to wipe the mutants out.

But Jeremy, too many movie references you've made, don't you have anything else? Okay, I read. I also watch plays. How about Javert from Les Miserables, who, through his belief and an unwavering commitment to the law, he thinks he is the rod of righteous justice and believes he's moral for doing so. All of these people, Osamandius and Javert, believe they were doing the right thing. Similarly, Sabilla in the film Kingdom of Heaven offers Baylion a choice to take control of Jerusalem to prevent a war, which Balian refuses, because he believes that committing murder to become king would make him no better than the person he was murdering.

She utters one of my favorite lines in that movie where she says there will be a day when you will wish you had done a little evil to do a greater good. In a lot of ways, Sibylla's temptation is understandable and she believed she was doing the right thing. Balian's choice is the diametric opposite of someone like Thanos who is willing to do a great evil

to prevent a greater evil from happening. And as an aside, by the way, another quote from Kingdom of Heaven that I just adore is what man is a man who does not make the world better. That phrase will probably get tattooed on my old wrinkly skin at some point. Kingdom of Fun is a great movie, by the way, and I think my son is now old enough to watch it. I know what I'm doing this weekend.

That being said, am I telling you that you should always make your villains sympathetic and complex? Absolutely not. But Jeremy, you said that sympathetic villains are more compelling and understandable, and that's true. But having evil villains without explanation and without remorse, Morse is simpler. Easier to design, easier to run, and it gives the DM the opportunity to throw wave after wave of creatures that the PCs can kill with no moral quandaries about doing so.

If in your world, orcs are evil, always in forever, and that they would kill and eat the PCs given half the chance, and if you're really lucky, the orcs would kill you and eat you in that order, since every orc wants every human elf dwarf gnome, Asimar, Tiefling, etc., dead, then killing them doesn't introduce any twinges of guilt in the PCs. They slaughter an orc patrol, then they can rest easy in the knowledge that they killed these monsters, and it probably prevented them from slaughtering innocence somewhere down the road. Furthermore, if you're running a game for younger players,

like middle school, maybe even high school, or people who are just learning the gaming system, keeping villains simple, evil for the sake of evil, makes for an easier game for them to understand and make clear moral choices in. Imagine you're 13 years old, by the way, playing your first D&D game ever, and you're attacked by bandits.

The party learns how to fight together and comes out victorious. The bandits should be portrayed as bad, period, end of story. Don't let it slip that one of them volunteered at the soup kitchen on weekends or give another one a crayon drawing in their pocket of her from their kid that says, I can't wait to you, come home, daddy, in crayon.

In cases when you have newer or younger players, keep the villains villainous and save the moral complexity for roleplay heavy campaigns. The decision on whether to use sympathetic villains ultimately comes down to your campaign style and your players' experience. Sympathetic villains like Darth Vader, as he was later portrayed, or Eric Kilmonger,

offer more realism and compelling role-playing with deep moral ambiguity and choices. But they require significant time investment to develop and explore. Conversely, a purely evil one-note antagonist provides clear moral stakes, is simpler to run, and often a better choice for games

with newer or younger players. This ensures your heroes feel fully justified in their opposition to these baddies. If you choose the approach that will create the most engaging and satisfying experience for your table, I'd be willing to bet that you and your players would have more fun doing it.

Wes, I hope this answered your question. If not, please shoot me an email or contact me again. I'd be happy to continue this conversation. Thank you all so much for listening. I'd like to get your feedback, whether on social media or email, feedback at taking20 podcast.com. Do you have topics you'd like to hear me talk about? Is there a particular tabletop news item you'd like me to discuss?

Please send me a message. Tune in next episode where another listener is asked about showing progression and advancement throughout a campaign, so I'll give you some tips for doing that. But before I go, I want to thank this week's sponsor, clocks. I have an old analog clock over here that only displays the hours. To get more detail about the time, I need to give it a hand. This has been episode 268 talking about sympathetic villains.

My name is Jeremy Shelley, and I hope that your next game is your best game. The Taking 20 podcast is copyright 2026 by Jeremy Shelley. The opinions or views expressed by guests are their own, and do not necessarily reflect those of the host. References to game system content are copyright their respective publishers.