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Originally Posted by Archon_Wing
Personally I thought Kirei and Kitsurugu were the most compelling, even if the later came so late. And then Rider was the spotlight stealer even if the depth was limited, so he clocks in at 3rd.
The first had the start of darkness and slowly declined into it. The later was just a tool of war trying to find some meaning in life and will just have to live with these regrets his whole life. But what else was there to do? He was a classic doomed tragic hero, or actually anti-hero in this case. There's just something striking about that empty look in his eyes, trying to search for survivors and a little emotion shone through when he did. Someone that's completely broken-- and that's a disturbing image this show will leave behind.
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Kirei's one of the most compelling villains in TYPE-Moon (if not the most compelling), the problem I had with the anime is that they completely messed up his characterization sometimes (they rushed a lot of things, cut his emotional reactions, cut his flashback about his wife's suicide, didn't alluded to his backstory of how he's a masochistic determinator, etc). He's so interesting that captures the attention of perpetually bored with this mongrel world Gilgamesh.
A good fangirlish ode/analysis of Kotomine Kirei someone made if you're interested in reading it. There're spoilers to FSN.