Hm, wouldn't say I've ever really had a crush on any characters, but the first I remember thinking were quite attractive (Looks + personality) were probably one of the girls from Outlaw Star, most likely Aisha.
I didn't really have crushes on anime girls/guys when I was young and watching only what aired on toonami for anime, but if I can speak for recent shows, it's a toss up between Chiaki Minami and Kirino Kousaka.
You don't know how much I want to say that it was Jin from samurai Champloo.
But depressingly it was that split personality yu gi oh guy with the narrower eyes. I even forgot his name cuz it was so long ago. It's sad T_T