Well here's for me...
Anime:
Ryoga Hibiki, the "Eternal Lost" boy. (Ranma 1/2)
Happosai, the perverted Grandmaster of Anything Goes Martial Arts. (Ranma 1/2)
Ranma Saotome, infamous God killer and aquatransexual. (Ranma 1/2)
Mu Tsu/Mousse, the myoptic martial artist Amazon. (Ranma 1/2)
Mugen, the breakdancing samurai. (Samurai Champloo)
As for games...
Games:
Chrono, the silent hero. (Chrono Trigger)
Frog, the determined knight. (Chrono Trigger)
Sephiroth, infamous badass. (Final Fantasy 7)
Those are all I can think of right know...well anyways, post away!