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Loving Naughty Characters

Posted on August 19, 2025August 19, 2025 By Misty Massey

Once upon a time, I was searching for career representation, and breathlessly submitted my rollicking pirate adventure, Mad Kestrel, to a literary agent recommended by another writer friend. After a couple of weeks, the agent responded, saying that she couldn’t wrap her head around a pirate as a main character, because pirates were essentially bad guys.

I think about this a lot, not because I’m still upset at being rejected. I love stories about tricksters and thieves. When I play D&D, I almost always choose an evil alignment (though never chaotic evil – that’s a step too far.) I’m a fan of westerns like A Fistful of Dollars or Maverick, in which the main guy isn’t anything like a hero. My favorite poem is The Highwayman by Alfred Noyes. It’s really no wonder I wanted to write my first novel about a character who lives on the edges of the law. So I wonder, from time to time, why I, a woman who has always behaved herself in the real world, would feel drawn to the outlaws and brigands.

I don’t really have an answer to why stories about such people are attractive to me. I know good and well that living on the outskirts of society is a miserable existence, and being hunted by the law is a neverending chase all over the place. In reality, not romantic at all. But in fiction, there’s a thrill to it. Maybe it’s the desire for ultimate freedom. Maybe it’s just wishing I could be someone else, someone who doesn’t have to show up on time and pay my bills regularly and make dinner every night.

What do you think? Are antiheroes cool? Are the white-hats the way to go? Spill.

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