D&D General Favorite villains from your games

TheSword

Legend
My favourite villains tend to be my own characters! They are sometimes ethically challenged.

As a DM, Strahd was a lot of fun to run. I like Manshoon and The Xanathar a lot. The titans Lutheria and Sydon from Odyssey of the Dragon Lords… and their minion Gaius.

As a player… Tom Lumpyface tops the bill. The Whispering Tyrant from Pathfinder and his minion Mathias.

I’m really looking forward to running the Ultimate Villain. No spoilers here though.
 
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Halaster Blackcloak.
Certifiably mad. Immensely powerful. Unpredictable, and yet at times Compassionate.

He kidnapped one PC (player left and it was her decision for her character to be kidnapped as it tied her to her backstory) to have as his muse and there is a strong possibility he cloned the PCs when they fell to Netherskull. They woke up at the entry pit underneath the Yawning Portal with only 1 item each of some significance (magical or otherwise). He is on their list as are their Clones.

But they are kinda busy at the moment. They have to defeat a Netherese wizard who has trapped them within a Time Loop to escape his own Maze, get a Conch of Teleportation to travel to Maelstrom in an effort to restore the Giant Ordning, defeat the Dragon Cult and possibly fend off the forces of Thay who are looking to take advantage of the situation with Tiamat's possible arrival (Tiamat Dracolich anyone?).
 
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GuyBoy

Hero
My favourite villains tend to be my own characters! They are sometimes ethically challenged.

As a DM, Strahd was a lot of fun to run. I like Manshoon and The Xanathar a lot. The titans Lutheria and Sydon from Odyssey of the Dragon Lords… and their minion Gaius.

As a player… Tom Lumpyface tops the bill. The Whispering Tyrant from Pathfinder and his minion Mathias.

I’m really looking forward to running the Ultimate Villain. No spoilers here though.
Ah, Gaius, may he not RIP!
We hated him so much that the party bard composed a song about him, but I’d run afoul of the moderators if I quoted it here!
 

Mad_Jack

Legend
Ah, Gaius, may he not RIP!
We hated him so much that the party bard composed a song about him, but I’d run afoul of the moderators if I quoted it here!

If the songs about the villain didn't contain vulgarity, clearly the villain isn't trying hard enough...
 

DrunkonDuty

he/him
My last campaign had a wizard called Ferridoon. He was a traitor who helped the BBEG defeat PCs army at the start of the campaign. He wasn't meant to live but somehow survived the first 2 encounters with the PCs. And they hated him. To make it worse he kept trying to do deals with the PCs to betray his boss. In the final fight with the BBEG Ferridoon took a whack of damage at the start of the fight and then hid, healing himself up, and doing a runner. He could probably have swayed the battle in the BBEG's favour. But alas he suffered from both extreme cowardice and chronic backstabbers syndrome. They never did catch him.

In my current campaign I've introduced a bunch of recurring villains. A pair of vampires who, even worse, are property developers looking to gentrify the PCs neighbourhood. A powerful Tuatha de Danaan who is a leader of the IRA. She wants to derail the (nascent) peace talks. A couple of coppers who have a personal vendetta against one of the PCs. (The player and I worked these up together.) The coppers and PC all wear the Mantle of one of the Knights of the Round Table. The last one, although not introduced personally, is a philandering fae lord who has a habit of leaving broken promises and women behind him. His plot is basically the song Delta Dawn.

The thing that makes all these villains successful is that they're recurring. It gives the players a chance to really get to know and dislike them.
 

gamerprinter

Mapper/Publisher
Well, not exactly a 'favorite villain', but one of my favorite villain books was the D&D 2e Complete Villains Handbook, a small blue vinyl covered supplement. It had a 20 question/step villain generator where the NPC character's stats were just one of those steps. Through the process you decide the class, etc, but more than that you begin to create traits and motives, opposing 'non-villain' traits to make the villain more human, and not just a pure monster of a person. It got into background, allegiances, weaknesses, jealousys, fears, over reactions. It was very detailed and was an excellent vehicle to design classic, poignant villains to face your adventurers with overtime, and not just for as single encounter. It built the networks for your villlains. I've haven't looked at, nor know the whereabouts of it, but it would be fun to re-review.
 
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