itachi is....soo fucked up it makes him cool.
kakashi is...i hate to say it but kinda a typical hero:
-lost parent(s)
-lost friends
-dead all around
-what...1000 jutsus? even though we've seen like...umm lets see summoning, chidori, earth decapitation, something to do with summoning lighting but...never happened, sharingan, mangekyou sharingan, does senen goushi (1000 years of pain) count?, water dragon thing...umm thats all i can think of now but, my point is, powerful enough to be the hero, not powerful enough (yet) to kill the main enemy.....