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Notes -
I love the Black Company. If you enjoyed it check out Malazan book of the fallen by Steven Erickson. He was directly inspired by Cook.
As for your post, the Black Company is pretty transparently about subverting expectations in fantasy around good/evil. A lot of folks argue it’s responsible for the massive wave of anti-hero/grimdark works in recent years.
A more interesting question to me is why gritty, darker, and honestly kinda fucked up stories have become so much more popular and mainstream. As @fivehourmarathon mentioned in another thread, ‘adult’ shows and novels now seem to refer to pointlessly gross violence or sex or both instead of actual adult themes with regards to philosophy or complicated moral decisions.
I think the "grimdark" label is often misapplied; remember, the setting that gave the trope its name is Warhammer 40K. It's not just a general "do bad things happen onscreen" measure; it's an evaluation of specific story elements.
"Grim" is a measure of the characters, in terms of moral motivations. The protagonist is an anti-hero, and the conflicts are gray vs. grey or gray vs. black. There are no classic altruistic heroes here; a grim story is cynical about people and how they work.
"Dark" is a measure of the moral center of the setting itself. No good deed goes unpunished; virtue is for fools. If there's a higher power, he's at best completely disinterested in justice, but he might just be Tzeentch straight up. Dark stories are cynical about ultimate justice and whether good deeds have meaning.
Sanderson is a good example of an author who is not grimdark, and he explicitly rejects the concept. Yes, the Elantris and Mistborn settings are deeply broken, but the protagonists are trying to fix things, and their efforts are rewarded. The brokenness of the settings isn't a grimdark immutable constant; it's the result of previous bad choices and calamities that can be addressed.
I think "dark and gritty" stuff could also be called "grimdumb." (See also)
There’s also
(Tvtropes)
See also the subtle differences that make something /r/grimdank.
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