Please enjoy the second submission for our latest contest: Your Best Worst Villain! See the rules and prizes here!
The most memorable (though not at all the deadliest) villain I have ever used in a campaign was, by far, Tattersleeve Quickwit. By the time they met Tattersleeve, the Player Characters were around level five and had gotten used to the “kick in all the doors, kill all the dudes, disarm all the traps, take all the treasure” method of play. I had them right where I wanted them.
Tattersleeve was a wandering goblin troubadour who performed musical numbers, told jokes, and demonstrated feats of tumbling, all poorly and in a high falsetto. While traveling through the town of Jarvis Brook he fell in love with a tavern wench named Lola. She would have none of him, despite his singing shrill serenades outside her window and regaling her with tales he thought were quite romantic. One day while Tattersleeve was attempting to woo Lola in the tavern, her husband came in with a posse, beat Tattersleeve to within an inch of his life (breaking both his legs in the process), and literally threw him out of town. Tattersleeve, unable to move, died of exposure to the elements while pining for his unrequited love on the side of the road. He then became a Taunting Haunt and haunted the area, shrilly mocking travelers who passed through. The characters met him after he had been terrorizing the locals for about a hundred years.
Taunting Haunts can be found in the D&D 3.5 Monster Manual V, and are one of the most devious creatures I’ve ever seen. They fixate on one character, following and taunting him or her until either the Haunt’s final wishes are met or the character wins a “Battle of Wits.” To win, the character the Haunt has fixated on must win three opposed Knowledge or Perform checks. If the character loses, he or she must give up one magic item worth five hundred gold or more. If the Haunt loses, it will relinquish one magic item worth five hundred gold or more and will leave that character alone forever. This does not mean it can’t fixate on another character in the party, though. If killed, a Taunting Haunt returns to existence and seeks out its victim after twenty-four hours have passed. On top of all that, Taunting Haunts have an ability called “Tripping Tongue” that allows them to cause a character who fails a Will Save to speak the exact opposite of what they had intended to say.
Tattersleeve differed from other Taunting Haunts in only one way: I had rolled his stats, and got two 18s. These immediately went into Intelligence and Charisma. Taunting Haunts are considered to have max ranks in all Knowledge and Perform checks. Tattersleeve fixated on the Half-Orc Barbarian in the party, who had naturally used Intelligence and Charisma as her dump stats, and had no ranks in any Knowledge or Perform skills. Hilarity ensued as Tattersleeve followed the party EVERYWHERE, shrilly taunting them, especially the barbarian, and constantly hindering their progress by making them lie at critical moments. He never actually damaged them, but instead went out of his way to save them on a couple of occasions, simply because they amused him and he wanted them around as long as possible. He was such a loathed presence that despite his help they tried on several occasions to kill him, but each time they brought him lower than zero hit points, he would disperse and reappear the next day. They couldn’t meet his final wish because his unrequited love died about a hundred years before they met him. Eventually, they gave in and stopped reacting to his taunts and he left out of boredom, but not before interfering with no fewer than three story arcs.
Image by Miguel Coimbra