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The fallen paladin who seeks to regain his status as a golden child. The lich who clings to life beyond the grave. The warlock who wants to get out of the Faustian bargain that seemed like such a good deal at the time.
The most disturbing and memorable villains in fiction are often tragic figures. How can you make this work in a game? What makes tragedy in RPGs?
Villains and Heroes
Usually, tragedy applies to heroes in famous books or movies. The tragic hero strives mightily but fails because of his own flaws, fate, or the unstoppable consequences of his surroundings. He usually winds up dead or defeated in the finale, or else wins a Phyrric victory. A good character makes a bad decision and regrets it, or better yet, knows he’s making a bad decision but goes ahead for a greater cause. You know the sort of thing: 300, The Odyssey, Hamlet. Everyone dies.
 So what the heck is a tragic villain? Villains usually lose in the big stories and adventures -- that’s their role. But by adding tragic elements to a villain in a D&D adventure, you can make him more interesting and allow for the possibility of redemption. A remote possibility, but gamers will remember the adventure that involves redeeming an evil monster. And even if the monster isn’t redeemed, he’s still more interesting if he’s got a tortured, bitter, or just plain messed-up past.
Tragic Villains
Here are concrete examples of the tragic type: 10 magnificent villains. Their fate is sealed, and their doom is assured.
1. The Fallen Paladin: This is the classic example: a paladin who makes one bad decision, then goes off the rails as his religious zeal turns to bitter ashes. Paladins and the like are wound pretty tightly, so when they fail, their motives can change quite abruptly as they feel betrayed by the people who once looked up to them or anointed them. Still, even a paladin-turned-assassin may have moments of conscience. Imagine a party scouting the bandit-paladin’s camp, only to see holy symbols and superficial signs of goodness.
2. The Half-Fiend: Cursed by birth is a great way to go for a villain; he can always claim that his very blood and nature are corrupt. It’s not his fault! He was born this way! Which is great, until he decides that there’s something non-evil he wants and his fiendishness gets in the way. Perhaps it’s a child, or simply peace and an end to the constant murder. What’s a half-fiend willing to do when he wants to get out of the network of entanglements and alliances that define him? Murder all his associates? But that would be wrong -- so instead he asks the PCs to help him with that… or is he just using them to eliminate rivals? The half-fiend’s blood rebels against him, he fights his own black nature, and he’s totally untrustworthy. But does that mean the PCs shouldn’t even try if he promises to reform?
3. Hideous Lover:Beauty and the Beast, the Hunchback and Esmerelda, or Othello and Desdemona; an outsider whose looks are all that stand between him and true love makes a fantastic villain. Pick a humanoid that looks nasty but might be good-aligned: maybe a drow, half-orc, bugbear, or ogre. Characters are drawn into the adventure because there’s a “monster”, but really, it’s the young man or woman’s family that strives to drive away the monster because they don’t want love to interfere with their own plans for their child. Any adventure built around a hideous lover has a built in plot hinge when the villain tells the PCs what’s really going on. Will they believe him? Ideally, if the party decides to kill him, the anguished lover shows up shortly after the death scene.
4. The Disguised Devil: In some cases, the hideous lover might actually be evil: an incubus, rakshasa, or a wizard with shape-shifting powers might put on a pretty face to falsely win a maiden’s heart. That’s not tragic, of course, that’s merely deceptive. It grows tragic when the villain actually falls in love with her, and the maiden’s love redeems the villain -- just before the PCs kill him, of course.
5. The Good-Aligned Monster: Many creatures we might think of as pure evil (the goblin, the demons, the red dragons) are only usually evil. The rare neutral or good-aligned example of a creature like this might try to warn a kingdom or city of the dangers it faces, only to be foiled by a party that kills it. In this case, of course, its dying words put the burden of fighting off the bigger threat on the PCs. Guilt as adventure hook works pretty well for all but the most mercenary and cynical players.
 6. The Misunderstood Monster: Some monsters kill or destroy by mistake. Frankenstein’s monster is the classic example, frightened by fire and meaning no harm. Other monsters might suffer the same problem; they need gold to line a dragon nest for the mating season, they curse those they touch, or they simply need to feed on cattle because they’re predators like werewolves or wyverns. Everyone assumes the worst. Their tragedy is that their behavior is destructive regardless of their motives -- so how do the PCs figure out that killing the monster isn’t necessary? I’d recommend using a single NPC who believes the monster is good, and tries to talk the PCs out of killing it. The monster then kidnaps “the only one who understands it” -- and is murdered when the PCs rescue the kidnap victim. Smart storytelling might show that the monster meant well all along, with a clue revealed when it’s too late.
7. The Faustian Bargain: A wizard or cleric who’s made a deal with the devil, and wants the party’s help in getting out of it. Ideally, a not very sympathetic character leans on the softest touch in the group -- and turns back to evil in the end, regardless.
8. The Cursed Villain:Dr. Jekyll and Mr. Hyde, the swan maidens of Swan Lake, the teenage werewolf, a vampire who fights the beast within -- they all want to be rid of their curses. Until then, though, they wreak havoc because the curse drives them to evil. The best part is that the villain is wracked with massive guilt. He might even confess when he’s not under the curse’s influence -- leaving the party with the dilemma of what to do with the confessed monster.
9. The Bitter Ghost/Possessor: The ghost who died a wrongful death, and seeks to correct it. However, the ghost’s appearance and powers keep killing off the vessels it tries to possess. Maybe possessing one of the PCs will help.... This sort of ghost might seem very reasonable until it gets what it wants, and then very reckless when the PC’s body is the one at risk. The perfect scene would be one in which the PC’s body is discovered in some compromising position after the villain has, for instance, ravaged or killed the object of his hatred, vengeance, or affection. This probably works best with a small party of PCs.
10. The Foolish King: A king who wants to avoid trouble instead invites chaos as his children fight over their inheritance, or he promises more than he can deliver to the gods (sacrificing a lover or child, perhaps). Even better if the king is an elf or dwarf, and the children have been scheming for centuries, and try to draw the PCs into their plots. Alas, the king’s hopes for peace are doomed, and his good intentions lead to bloody civil war. For a fine example, see “Lear the Giant King” in Dungeon #78.
The Fateful Choice
 The most important scene for a tragic villain is the one in which the party offers them a chance to choose the good side, and they either accept it (and tell the party some great task they must undertake to stop the plans he has already set in motion), or the villain rejects it, embracing darkness completely and attempting to destroy the very party that showed him hope.
How do you set up that choice? It’s difficult, but I’ll use a couple of examples.
Redemption and Regret: The paladin who’s now a death knight may have clues scattered around his gloomy castle: poetry to his lost love, a garden of dark flowers that whisper of his guilt, a chapel filled with implements of flagellation and atonement. Sure, he’s evil, but for a reason. If the party can recover the bones of his dead lover and lay them to rest, the death knight’s reason for vengeance and evil fades -- and he departs the world. But only if the party makes certain that redemption is not only possible, but likely. Perhaps it requires a speak with dead spell to ensure that the villain hears the final words that send him to an eternal grave. Perhaps astounding Diplomacy or the discovery of a lost heir does the trick -- but something shows the villain that forgiveness is possible. Tough to pull off at a hack-and-slash RPG table, but it has been done. See “Rose for Talakara” in Dungeon issue #25.
You’ll Never Win!: Another option villains simply love is to threaten the party with the death of innocents, say a group of harmless gnome tinkers. The party confronts him with the information that his plan has failed; perhaps the gnomes themselves disarmed his traps. In this case, the villain hesitates for one round talking and possibly bluffing about his minion’s deeds -- long enough for one of the gnomes to disarm or disassemble a crucial device. When the villain discovers this, he snarls “Treachery!” and rejects the light side -- and the party is hard-pressed to defend the innocent bystanders. The villain’s hesitation helped them win, and makes for a stronger last scene.
Conclusion
Tragic villains are a little more interesting than the usual types; they often draw a party of heroes into their complications and their problems. Most will still ultimately remain evil and be defeated -- but the potential for a story of a villain redeemed makes them interesting.
About the Author
Wolfgang Baur is plotting his elaborate-yet-ruthless vengeance even now. His escape hatch is a series of cleverly-disguised blogs like Open Design, where he shares further design secrets.
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