Sympathetic Sociopath

Question: OK, my story is, more-or-less, meant to be an embodiment of every negative thought, feeling, impulse or emotion ever felt by the "outcasts" of adolescent life. I know this is more often than not a very cliched subject, but I plan to make mine stand out for sure. Anyway, it centers on one boy in particular who, though I wouldn't exactly call him insane (for multiple reasons), snaps and systematically exacts punishment on every solitary person who ever hurt him in any way. Far from being a typical "you bullied me, so I'm killing you" type of story, I want this character and the plot to bring to mind certain questions society really seems to ignore. For instance, "How exactly does your age make you better than me?" in regards to the immensely ageist attitude of many modern societies. Or "What possible reason could you have for hurting me when you don't even know me?" in relation to things like bullying. But back to the question, this boy is more a tragic figure than just an evil villain. And he is much more a secretive, sinister, almost evil genius-ish personality who is impossible to catch or find instead of just a teenager who went psycho. I'm wondering how I can portray him as both sympathetic and yet sadistic. I want the reader to understand his emotional and spiritual pain (he is also revealed, later in the story, to suffer self-loathing) and why he does what he does, yet see how much pleasure he feels in doing the things he does. Note: He only targets people who have wronged him; nobody else, under any circumstances. Any help you can give would be awesome!

Answer: While I can't deny that there are many examples of successful stories involving characters like this (for example, Kill Bill or Hit Girl from Kick Ass), the danger is
is that they often come across as shallow. The pain they inflict on others so often seems out of proportion with the injuries they have received. The things others have done to them come across merely as an excuse to allow them to go on a rampage.

There are thin lines between a believable revenge character, a two-dimensional character (like Hit Girl), and a monster of the kind typically featured in horror films such as Halloween or Friday the 13th.

I think the problem is that sociopathic violence is not something most people can empathize with. You might sympathize with someone made insane by ill treatment combined with a sociopathic illness, but most people would not seriously consider a murder spree to be an acceptable way to cope with their problems. (I'm not sure that's the message you want to deliver either. But, like I say, that's Kill Bill.)

One approach is to tell the story from the point of view of someone other than your sociopath. That's how most horror films work. The main character is an potential victim and the impact character is the monster who forces the main character to resort to violence to survive, and thus become a stronger person.

A second approach would be to have a bullied main character who is tempted to go on a murder spree when he meets a sociopath who does that sort of thing, only to change his mind at the climax.

A third possibility would be to have your sociopath and just accept that the readers may sympathize but not empathize with him.

And a fourth possibility would be to have a non-sociopath who the reader can emapthize with who is put into a situation where killing is the only possible solution.

The trouble is that once you make the character sinister, he stops being tragic - rather like The Phantom of the Opera.

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