Man, this is really tough. This is in order by series because I love all the characters and can't really decide, so bear with me.

Kamina (Tengen Toppa Gurren-Lagann)
Simon (Tengen Toppa Gurren-Lagann)
Nia (Tengen Toppa Gurren-Lagann)
Saki Kasukabe (Genshiken)
Chika Oguie (Genshiken)
Kanji Sasahara (Genshiken)
Hironobu Madarame (Genshiken)
Kyon (The Melancholy of Haruhi Suzumiya)
Youichi Hiruma (Eyeshield 21)
Aizen Sousuke (Bleach)

Crap, that's 10 already isn't it? There are so many more. Well, such is life.