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The pic along with the file name makes me think of Bloody Tears, except it's brown. Chocolate tears? Is that Chocolate Rain? I have no idea where I'm going with this.
Binding of Isaac would be my guess.
It's not Bloody Tears and Binding of Isaac.
No, don't give up!
I'll try to help *adds another image*.
Caution, nightmare fuel :p
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Well that's definitely creepy.
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Exoanthrope: Well that's definitely creepy.
I doubt it. Can't even find it on mobygames:
http://www.mobygames.com/search/quick?q=creepy
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almabrds: No, don't give up!
I'll try to help *adds another image*.
Caution, nightmare fuel :p
Deadbolt? Haven't played it yet but your pic reminds me of that skull in its artwork.
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almabrds: No, don't give up!
I'll try to help *adds another image*.
Caution, nightmare fuel :p
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F4LL0UT: Deadbolt? Haven't played it yet but your pic reminds me of that skull in its artwork.
No it's not.

Another hint:
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I still stand by that it's creepy.

I've never played it, but the style reminds me of Neverending Nightmares.
If your first picture wasn't titled Castlevania, I would guess from the last picture, that is IS from some Castlevania game. So, something similar to Castlevania?
I played that game.... where could be this monster from... is it Quake?
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Lifthrasil: If your first picture wasn't titled Castlevania, I would guess from the last picture, that is IS from some Castlevania game. So, something similar to Castlevania?
No, it's not like Castlevania.

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LordEbu: I played that game.... where could be this monster from... is it Quake?
Incorrect.

Another image:
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This will be the last hint.
If no one guesses, after looking at all the images, I'll reveal the title.
I'll wait one day or two.
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sooo... the blue and red, coupled with the icons and the new pic could be Enter the matrix. But the creepy face and monster make me think System shock. But then again, if it's all being cryptic and just alluding to a theme then it could be Deus Ex or even Bioshock.

colour me stumped.
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Ominousrobot: sooo... the blue and red, coupled with the icons and the new pic could be Enter the matrix.
The first picture is a drop of water and whiskey.
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Exoanthrope: The pic along with the file name makes me think of Bloody Tears, except it's brown. Chocolate tears? Is that Chocolate Rain? I have no idea where I'm going with this.
It's not chocolate, or blood, Exoanthrope :p
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Ominousrobot: But the creepy face and monster make me think System shock. But then again, if it's all being cryptic and just alluding to a theme then it could be Deus Ex or even Bioshock.

colour me stumped.
The creepy face pic shows the most powerful enemy.
When it dies, it creates a portal the player can use.