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Originally Posted by Nyssa
What an excellent post, CWatkinsNash!!
I think the show, Dexter, is an excellent example of a sympathetic bad guy. I have only watched the first 2 seasons (out of 5), but in that time you learn all about his back ground and how he came to be what he is today. Your friend would probably hate him & the show.
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Since I live deep in the country with neither cable or access to broadband, I've not seen either of the Dexter programs or Human Target (could be that's the reason I read as much as I do

), but Lois McMaster Bujold has a character in her Vorkosigan Saga books that is definitely a sympathetic bad guy. Konstantin Bothari, bodyguard and companion to Miles Vorkosigan.
Quoting from Wikipedia:
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Bothari's personality is variously described as fragmented, insane, or chameleon-like. While a child, his mother repeatedly sold him to customers until he was old enough and large enough to fight back. His deep psychological scars and trauma can surface with the right stimulus, converting him from a cool-headed warrior to a sexual psychopath in an instant.
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Sounds pretty terrible, but as I read the series I couldn't help but feel sympathy and some kind of understanding for the man. He's actually a decent, caring, honorable and deeply damaged man.