Okay, my last, similar thread got deleted because of the lack of reasons why I chose my top 5.
Sorry about that, but the reasons were real obvious.
GLASSES. It isn't a favorite character thread, but a favorite GLASSES character thread.
That aside, as I've said, it's all about the glasses!
My top 5 would be:
Rider - Fate Stay Night/Hollow Ataraxia
Kijima Saki - Hayate no Gotoku
Nagato Yuki - MoSH
Azuma Satori - Bamboo Blade
Ciel - Shingetsutan Tsukihime