This is from an article in The Guardian:

What is it about hitmen? (And apologies to all you feminist hitwomen out there, but "hitperson" lacks that je ne sais quoi, so I'm sticking to the masculine form.) They're all over the bloody place - and, pace Tom Cruise in Collateral, they're hardly ever villains. They're loveable and bumbling like Colin Farrell in In Bruges, loveable and inebriated like Ben Kingsley in You Kill Me, machinelike but principled like Timothy Olyphant in Hitman, or possessed of fabulous superpowers, like James McAvoy and Angelina Jolie in Wanted. How is it that characters who are, essentially, mercenary murderers are nowadays being offered up to us as heroes, whose killing skills we are expected to applaud and admire?

But far from being a romantic rule-breaker, ronin or rebel operating beyond the restraints of society, he is a mere tool of the system. The ultimate businessman, in fact. Isn't it about time we stopped treating him like one of the good guys?

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I presume. There was a dateline special a couple of weeks ago about an entertainer who hired a "hit-woman" to kill his wife. It was a complicated story and the woman wasn't really a "hit-woman" and she worked with the police to nail him, but the attempt was made. He even told her how to kill his wife.

Some people...

Deirdre
Hey John...

While not addressing the good guy image, to me, the dark freedom from societal rules a hitman lives with is part of the draw. Much like the character the Kurgan from the movie Highlander. He was an evil, evil guy but he did as he pleased with these mere humans without regard. In a perverse way there is an esctacy in that lack of restraint. "To burn out before he fades away..."

As far as your statement of hitman being "a mere tool of the system", I think they actually are tools outside the operating zone of the system. I made that point in my book Justice is Coming. The antagonist used the system to feed his wealth, but has an evil doer, the dark man, who does his bidding outside the system to keep things running smoothly. But in the end the antagonist meets a surprise ending at the hands of an unexpected person who also stepped outside the system to seek justice because that was the only way it would be achieved.

Oh, and if you look on my page at the cover of Justice, no I don't romanticize hitmen, not me!

Just my two cents (hopefully worth the price of the copper to make them...)
Just to clarify, I didn't say, "tool of the system," that's from an article in The Guardian (linked to above).

But it is interesting. We've talked before here on Crimespace about vigilante justice and how very, very few writers seem to be able to find drama and conflict within "the system." I think a lot of old-style noir was about the conflict of at least trying to live within the system.

It's really the main thing I loved about The Sopranos, the central conflict of Tony wanting to be a respected businessman and also loving the power that came with being a mob guy. If he was happy being just a mob guy he wouldn't have been as interesting -- well, I guess you see that with the rest of the characters in the show and that's why they weren't the main character.
I think they just fill the same niche as the Gun Slinger in popular fiction.
Thats why I like Block's Keller so much. Decidedly not a good guy.

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