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I vote for five people: Emiya Kiritsugu, Emiya Shirou, Archer, Tohsaka Rin and Kotomine Kirei.
I vote Emiya Kiritsugu not for the Fate/Stay Night, rather for Fate/Zero. His story is one of the saddest story ever written. I could say that his whole life is a tragic. Well, I'm happy that at least he finds peace in his later days before he died.
Emiya Shirou is not a dumb stick like everyone think. I admire his ideal and his will. Not many people have as strong will as his, especially in the game. UBW shows what he's capable of and HF shows his mental growth that conclude the story very well.
Archer is someone whose life is also a tragedy. I won't say it much here because it would end up being a spoiler. I would just say that he wasn't wrong.
Tohsaka Rin, the person who is not actually the deepest heroine in Fate/Stay Night but still have a very good background in term of characters. She loses everything in the previous war, yet she stands firm and not waver through the course of war.
Kotomine Kirei is an unusual choice of character for many people. Please note that he's deeper than he is in the anime. His motive and question about being is deep and philosophical. Although he looks totally different from Shirou, he's actually very similar but yet different like the faces of the same coin. Read HF and you will find that this character is very well written.
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Fate/Zero: This was the tale of a man who, more than anyone else, believed in his ideals, and was driven to despair by them.
Madoka: This was the tale of magical girls whose wishes are pure and by them are driven to despair.
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