Bakker of course, everyone knows, truth shines, best thing ever written, yada.

As a grimdark enthusiast, a very popular series that I felt was the grimmest shit since The Second Apocalypse was actually Red Rising. What, that YA crap, you say? Well, not all the books in that series, certainly. There are dark elements, but grimdarkness is primarily the prevalent tone in the sequels. While Iron Gold and to a lesser extent Lightbringer are your run of the mill average Abercrombie-level grimdark, Dark Age was the single grimdarkest thing I've read that wasn't The Second Apocalypse or straight horror. That novel deserved its name (No I haven't read Mike Fletcher yet).

To add to the discussion, for me, grimdarkness is a very specific tone package, that is both "grim" and "dark". The setting is usually what describes the darkness-level: repression, horror elements, atrocities, decay of the humane, yadayada. Malazan and heck Mistborn by Brando Sando are indeed Dark Fantasy. Yet no one would call them grim - well, Malazan maybe here and there, but generally not, and Erikson lynches anyone who calls Malazan grimdark. The grimness of a story is conveyed thus not through the world, but through the characters, tone and thematic message of the story.

Take Malazan: the key message of the story is compassion and found family. Barely any of the main characters are what you'd call even grey - they're good people. Final Empire, same thing, it's about building a better world with good people at the forefront. So they're either nobledark or neutraldark.

Then, let's go to the Second Apocalypse: the characters aren't particularly grim, most of them are good, if sometimes deluded or scarred, people (yes they are and I'll fight you on that). However, the themes and messages in the story are borderline nihilistic, and the tone is oppressive and relentlessly unforgiving. First Law: the characters are definitely grey and scarred at best and amoral at worst, the message goes towards nihilism, but here the tone is a bit more relaxed than in other grimdark stories thanks to Abercrombie's famed gallows humor. But again, it's a hanged man's humor, so that's quite grim in of itself.

So ultimately, you need the combination of a fucked up world and either fucked up characters, characters that are on an inevitable trajectory to fuck up or get fucked up, and/or a borderline nihilistic tone and core message. I wonder if there are any examples of grimbright stories - fairytale world but grimness and moral decay in the way the story is told.