t work I sit next to a hypothetical guy – he loves asking off the wall, unexpected questions. And that’s fine – I enjoy finding myself thinking up answers (one was, “Which Greek hero represents you?” My answer, Achilles. You gotta love how he went on strike because of bad management practices). But this time he asked me, “What are your three favorite villains?”

That’s a very interesting question, and I was amazed at how quickly it stumped me. Sure, I read a lot of novels, scifis and fantasies. But really, are there truly villains you’ve read that aren’t just cardboard cutouts, that give you a chill or a thrill? Even extending it to films and all media, it’s a very curious question.

My first thought was Rudi von Starnberg, the organizer of the prince-switching plot in Royal Flash. He was just the sort of guy I liked (and wished I could be) – ornate and cool and funny. He really captured it for me. But the more I thought about it, I liked him for being him, not for being a villain. So I had to withdraw him.

Immediately after that, I decided that General Woundwort from Watership Down was a great villain. He’s all powerful, he’s frightening, he’s missing an eye (and yes, he’s a bunny, a bad, bad bunny). He doesn’t make overly stupid mistakes, he has great lines and his character flaws aren’t artificial. As it was later said, General Woundwort’s body was never found. It could be that he still lives his fierce life somewhere else, but from that day on, mother rabbits would tell their kittens that if they did not do as they were told, the General would get them. Such was Woundwort’s monument, and perhaps it would not have displeased him.

Yeah, so he’s in.

After about thirty minutes and a scrum call later, I came up with the second: Sauron from the Rings trilogy. Like Woundwort, he’s got an unbeatable army at his back. But he’s so perverse and far-gone that you don’t even know if he’s even recognizable as a human anymore. All he does is lurk in his tower and sweep for the hobbits. His efforts are sound, he doesn’t do stupid-leader-stuff, and his end feels earned. So, yeah, I’d put him in.

The next-pod-guy and I kicked ideas back and forth and finally he mentioned Darth Vader. Yes, I’d go with that (even though I no longer follow the movies and find it too much of a grinder for my tastes). But the classic Vader, the bad guy you eventually feel sympathy for, he’s a great Villain. Choking the shit out of admirals, classic.

Only after I came up with mine did we look online to see what others mentioned in various articles. Sure, there were famous books, many of which I’d not read and some villains that baffled me (Captain Hook? What are you, four years old?). But the surprising final one I wished I’d thought about was Milo Minderbinder from Catch-22, who turns all of World War Two into a gigantic corporate venture. Yeah, he was a good villain, an unseen villain, who only comes out of the woodwork near the end when he has his own army, a monopoly on brothels, and his own air force. Perfect.

Oh, and one I came up with much later that nobody picked, Moby Dick. Yeah, there’s a villain for you. Or would it be Ahab. Both?

Think about it. What villains define your fiction?

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