Ideally something like Akazukin to Yasashii Ookami.

Any genere is valid, but no half assed drama

Things like Shamo, 17-sai., Sundome
Less hardcore things like Vinland Saga and /Blush-DC. are also OK,
Sad moments like the end of Holy Land, or Berserk before it turned to crap.
or even characters in constant depression like Kono S o, Mi yo! - Cupid no Itazura are fine too.

If you read "Dark Stuff", and Death Note was your first thought, please don't even bother.

maybe:
Kimi no knife
Akumetsu
Manhole
Sugar Dark: Umerareta Yami to Shoujo


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this was my first thought when reading the title...

I strongly recommend to go to the 'looking for' section and search for 'dark'.

there's also the Dark Ambiance tag

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in need of romance?
uncommon, sad, sweet

Kurozuka
Toukyou Akazukin
Elfen Lied
Ciguatera more depressing than dark.
Battle Royale (novel) because the manga is crap
Hakomari (novel) less dark, but its awesomeness will cover for it

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What I like in Trivial Pursuit style. Pick your category:

It's a romance and comedy and hard to find completely scanned (you have I order it online)

Jiu Jiu by Tobina Touya

Surname first /\
|
Sorry I can't link.

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"'The lives I've taken will be paid for with my own life.' That's one way to look at it...but it doesn't mean they come back once you die. Lives can also be paid for by the sword; by redeeming yet other lives. That is why 'Hitokiri Battousai' is still alive in the Meiji Era."

don't click this link...

Toukyou Kushu
and since you mentiontioned sundome I'm sure you are already reading Ibitsu (OKADA Kazuto)

Thanks
I already read:
Kimi no knife
Sugar Dark: Umerareta Yami to Shoujo
Toukyou Akazukin
Elfen Lied

Ciguatera was on my wish list. I'm checking it again.

Akumetsu: I dropped it after reading lots of chapters. It turned too slow.

Battle Royale
Hakomari
I've been avoiding fan-translated novels, but it might be a good time to start with them.

I'll try:
Kurozuka
Toukyou Kushu
Manhole

As for this, I'll wait for more chapters to be released.
Jiu Jiu by Tobina Touya
Ibitsu (OKADA Kazuto)

Thanks again

The Voynich Hotel

Kurozuka was kinda lame, in my opinion.

Battle Royale is available in English as a book (it's not fan translated) : http://www.amazon.com/Battle-Royale-Novel-Koushun-Takami/dp /1421527723/ref=pd_sim_b_4
But I read it in Italian so I don't know how accurate and good the English official version is.

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What I like in Trivial Pursuit style. Pick your category:

Give these a shot:
Anorexia - Shikabane Hanako wa Kyoshokushou
Satanister
Both are Dark and Creepy as Crap...

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Beware the Fox, for while he is wise, he is also mischievous and cunning!

How was that version? It might be good to practice my Italian.

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Ubel Blatt : Dropped it, couldn't adapt to the art / MC

The Voynich Hotel: Suspended it, I remember it was fun, but not that fun.

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Anorexia - Shikabane Hanako wa Kyoshokushou
Satanister

I like both concepts...

The translation is fairly good. I don't know your knowledge of the language (I'm Italian) though so I can't really recommend or not recommend it, I'd say the book is medium difficulty. This is the edition I own anyway: http://www.amazon.it/Battle-royale-Koushun-Takami/dp/88045868 77
Still I heard that the English version I previously posted is a new improved translation and it's good, at least according to internet. The choice is yours still.

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What I like in Trivial Pursuit style. Pick your category:

I second Hakomari, it does get darker in the latter volumes.

Kurozuka is awesome. But check the anime, in my opinion its better

I wish there was more stuff like Kurozuka and Sugar Dark around.

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Friedrich Nietzsche (1844 - 1900) - "Man is more ape than many of the apes."

Jean-Paul Sartre - "You are--your life, and nothing else."

Henrik Ibsen - "The majority is always wrong; the minority is rarely right."