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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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When I use the term Grimdark, I think it is etymologically tied to its role in 40k, by function. The 40k setting is grimdark because that makes gameplay work well. Everybody sucks and there are no good guys, so whichever faction you pick its all the same you're trying to kill the other guy. One guy isn't forced to pick being the bad guy, both sides are bad guys, all the damn sides are bad guys. You can be part of the slaughter xenos and execute anyone who thinks bad guys, the fight for the sake of fighting bad guys, the kill everyone and stack their skulls bad guys, the hivemind eat everything swarm bad guys. The fun is in picking your bad guy and leaning into it, not in trying to argue that the IoM are actually the good guys, or that Tzeentch is actually the good guy, or whatever.
Something like Succession is a very different example of well done grimdark, everybody sucks and no one is the good guy, so all the maneuvering and fucking each other over is just good fun. I don't give a shit about Roman or Shiv or Kendall, and for God's sake you can't really like Logan; so every twist of the knife is great no matter who its stuck in.
They're great when they understand that their grimdarkery is window dressing to make gameplay work. Where they fall apart is when they get up their own asses about "this is how things really are, maaaan." ASOIAF is great fun, but when GRRM or GoT fans get uppity about realism I lose interest.
I like everyone except Roman though, he's a disgusting sexual degenerate who kills tons of people through negligence.
I think Roman is actually my prohibitive favorite of the four kids? I sympathize with Tom and Greg to an unfortunate degree, but they're all pretty morally reprehensible in their own ways. Still don't like any of them really, any sympathy I have towards a character is sort of an internal cringe "Oh God am I like that..."
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Yeah, I'm not sure how well-accepted that taxonomy or this taxonomy is (or how applicable it is to settings as a whole: even WH40K has bright spots like Ciaphas Cain), but it does seem more useful as a way to talk about adult themes in philosophy or complicated moral decisions, as opposed to the gritty, darker, and honestly fucked up side.
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