D&D Villains: Sympathy for the Devil

Salutations, nerds! Today, I’m going to talk about villains again, and this time we’ll be discussing sympathetic villains in your fifth edition Dungeons & Dragons games. I’m talking about the wizard whose been vivisecting people trying to come up with a cure for his wife’s ailment and save her life. I’m talking about the planar being who has cut a swathe of chaos across the land trying to get home. I’m talking about the blackguard who was betrayed by his people and had his heart stained in darkness. These are the D&D villains you almost want to fix. The ones who tug your heartstrings and make you hesitate to kick their butt. These are the Mr. Freezes, the Princess Lunas, and the Magnetos of your D&D campaign.

sympathetic villains
The Will from Saga; Kingpin, Magneto and Doctor Octopus from Marvel Comics; and Mr. Freeze from DC Comics are all villains. But the best bad guys often have stories the heroes (and audiences) might relate to or at least understand.

D&D villains with the feels

At the end of the day they have just done too much bad for you to let them off with a warning. They must be stopped. They must answer for their crimes. At the end of the day though, you can understand why they did it in the first place.

D&D villains like this are the ones you throw at your players when you want them to feel things. They might well decide they want to try and rehabilitate, and that’s all right, but don’t get too attached because that rarely ever happens. These baddies are tricky, depending on what level of bad we’re dealing with, so let’s get right to it.

As a Big Bad

A sympathetic Big Bad — now this one is difficult to handle, because by the time the characters get to them or become aware of their existence, they should still be a 16th-level+ threat and therefore watching their fall from grace isn’t really an option.

There are ways to handle this. You could find diary entries like in Curse of Strahd (but don’t mistake him for an actual sympathetic villain, he’s an incel with fangs; “I don’t want my loved one to die” is sympathetic. “I’m going to make the whole plane suffer because this girl won’t date me” is just entitled), or certain places in the setting where time and space have worn thin a little bit, enabling the characters to actually view what happened there once.

Firsthand accounts from NPCs are also excellent for this kind of thing if you’re careful. Set up people in the world who know things and give your characters reasons to ask. This can make for some intriguing dialogue.

One important thing to remember is the Big Bad is going to be your last fight. The capstone of the campaign. Don’t cheat your players out of a fight like this. The Big Bads can be sympathetic villains, but never so much that they’re redeemable. The things these D&D villains do should be so bad, the characters have to get rid of them anyway.

D&D villains
Count Strahd von Zarovich is one of the greatest D&D villains of all time. His tale might garner some sympathy…but he’s still an evil villain you can feel good about foiling.

As a threshold boss

Now these baddies, they can be redeemable, but you probably still want the fight to happen anyway.

Take that wizard looking to cure his wife, for example. Or a bad guy whose loved ones are being held hostage by the bigger bad. They might ruefully admit they wish it didn’t have to be this way but that if they don’t do as they are told people they care for will suffer for it and attack the PCs anyway. You might have them go down and have the PCs find them unconscious but not yet dead and give them the choice whether to finish them or not.

Another case you can use for a villain like this is a possessed person, whose butt you have to kick to force whatever is driving them back out.

As an encounter boss

As an encounter boss, sympathetic villains are even easier to cook up. A dryad whose grove has been burned and flayed by the bad guys and is mourning too much to be reasoned with yet might make for an excellent encounter.

Any time a monster is rampaging because its eggs were taken, it’s this kind of villain. Any time somebody has broken into some kind of sacred area and the guardian of that area comes out to kick some tail, it’s this kind of villain.

And since it’s only an encounter, letting the characters talk their way out of a situation like this is always a valid option. Simply fighting until the creature is too tuckered out to continue is also a valid option if your table rolls this way. And, of course, just killing them anyway — a lot of parties will do this regardless of what the reasoning is.

As a minion

It’s hard to drum up sympathy for someone who is being manipulated like this and who can’t handle themselves, but these weasely minions have their places. Any time your characters need to juice someone for information, these will be the frightened underlings they go to for it. Making minor bad guys pee themselves makes the characters very happy, usually. Sometimes, you want them to feel powerful and situations like this are great for that.

One time, my players were on an airship being invaded by orcs and one of them cast detect evil. I sarcastically said, “All of them but one of the orcs are evil, he just kind of got bullied into it.” They proceeded to make a shield wall around that orc and kept him around.

Suffice it to say…there was a paladin involved in that one. But it was pretty fun and added a lot to that particular game.

And now for a shameless plug

Once again, gonna try to keep this brief but I just want to talk about my current work in progress, which will hopefully be coming out around December.

The aesthetic of the 1920’s. Summoned demons doing things like delivering messages, working industrial machinery and providing lighting for streets. Organized crime. That is Torchlighters in a nutshell. I like to think I’ve got a certain wordplay and humor I bring to my articles and I do my best to bring it to my fiction as well, so if you’re at all interested, check me out on my Fortune Favors blog for regular updates on the project. Hope to see you there!

I now return you to your regularly scheduled nerdfest.

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Speculative fiction writer and part-time Dungeon Master Megan R. Miller lives in southern Ohio where she keeps mostly nocturnal hours and enjoys life’s quiet moments. She has a deep love for occult things, antiques, herbalism, big floppy hats and the wonders of the small world (such as insects and arachnids), and she is happy to be owned by the beloved ghost of a black cat. Her fiction, such as The Chronicles of Drasule and the Nimbus Mysteries, can be found on Amazon.

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Speculative fiction writer and part-time Dungeon Master Megan R. Miller lives in southern Ohio where she keeps mostly nocturnal hours and enjoys life’s quiet moments. She has a deep love for occult things, antiques, herbalism, big floppy hats and the wonders of the small world (such as insects and arachnids), and she is happy to be owned by the beloved ghost of a black cat. Her fiction, such as The Chronicles of Drasule and the Nimbus Mysteries, can be found on Amazon.

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