I would have to say this one was definetly the most cruel, seeing that most of these characters were kids, then you see them losing family, a character wondering if he is really living, destruction of a dimension and loss of a mother.
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...what?
FFX was billions of times more dark than FFVIII ever could have hoped to be.
I don't think FFIX is anywhere close to being even considered dark at all. If anything, maybe Memoria is a bit dreary, possibly Pandemonium as well, but otherwise it's the transition from the Darker games of FFVII and FFVIII to the lighter side of Final Fantasy with FFX.
Basically, the character designs were done so that when playing this game, it seems really light-hearted and cheerful, almost like a childs program or game, but when you discuss the ideas behind it, it seems much darker.
IX was a dark game not just because of a the destruction in it but also everything that is implied along with that. Take Vivi and the fact he and the other mages were a race bred for killing and then there is Zidane own similar struggle learning that he isn't even from Gaia (or maybe even alive), the losses Garnet and Freya experience. This comes together as a dark game from all ways.
That's one thing I like about IX, it LOOKS like a happy little game but when you start paying attention to the events going on and the themes in the game, it's one of the more mature FFs.
Ok the Darkest FF game is Definitely Tactics.
You can go through a list of all the characters in the game and before the ending the only people who are alive are your party and a couple others.
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The ending? Your whole party and in fact almost everyone left is dead! your whole adventure is forgotten for 200 years and your lame friend gets all the glory. One of the only guys to survive is orlan (Orlandu's Son) and in the epilogue it says he is burned at the stake! Horrible...
Did anyone else thinkt that the music that played when you fight Necron is creepy? You can hear the souls of the dead wailing in the background D: