The Darkness That Comes Before
This book and the Prince of Nothing trilogy, as well as the other books that follow, are so dark that you'll need a shower after reading them. And therapy. This bad-boy was nominated for the Locus Award for Best First Novel. It's a deep, philosophical read that demands your full attention, rather than being a light, pacey read like, for example, some of the young adult entries on this list. The prose is deep and enthralling, thick as rich chocolate but with the mental nutritional value of, like, kale or something. , the content of the book is deeply philosophical and intellectual, not in an 'everyone sits around and discusses the meaning of life' way, but in that the underpinnings of the characters and plot draw from eastern and western philosophies. The plot is epic and with many threads that play out across the series. Both monstrous and human entities within the book are horrifying, and the way magic-users operate is particularly unsettling. Read this book if: you like more intellectual novels, but don't want to miss out on all the sex and violence either.
Books in The Prince Of Nothing Series (6)
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The vast scope of The Darkness That Comes Before is very redolent of Steven Erickson's Malazan Book of the Fallen saga, though the characters are less gray, and the story more focused.
Also try George R.R Martin's A Song of Ice and Fire, which is very epic and very gritty but way less philosophical. I'd also say it's more "character driven" as a whole than is The Darkness that comes before.
Another series that does that is Abercrombie's First Law series (starts with The Blade Itself) and Richard Morgan's The Steel Remains.
I'd say you'll also probably find Acacia by David Anthony Durnham a good read too -- there are gray characters, an exotic landscape, and world-ending powers at play in the background.
For another fantasy about war, look at John Marco's Tyrants and Kings trilogy. It's a great read with a cast of grey characters.
Another gritty military fantasy you'll probably like (though it's less cerebral than The Prince of Nothing) is The Black Company by Cook.
The Godless World series by Brian Ruckley is dark, atmospheric and very gritty, though it lacks some of the polish of the other series. The series never full lives up to it's potential, however.
For a deep character-driven fantasy you might try Daniel Abraham's The Long Price Quartet.
For a gray fantasy with lots of politics, different kingdoms going to war, a cast of ambiguous characters, adventure and magic, check out Paul Kearney's Monarchies of God.
Like pointed philosophical bits about the state of mankind thrown out by the hero? Try Mark Lawrence's The Broken Empire trilogy. It has a gritty and dark world it's probably the closest in theme and style you'll find to Bakker's works.
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