I remember there was an episode in The Land of Waves Arc and Sasuke "died". Man, I started to cry...i had just started watching naruto and sasuke was my favourite character...i just cried. I practically bursted into tears. I don't have a "one saddest moment". All the ones listed above are the same. That's the most awesome thing in naruto: whatever happens, you'll always feel the way the character feels. It's like you are with them, right there, in their world, knowing their feelings, feeling the same, trying to not cry eventhough you know that you can't...And the music..it gives you chills. Moreover, i still feel and always will that naruto has become MY personal way of life. By seeing the characters' sadness, i become more determined to live my life to the fullest, and not have to feel the pain they experienced. They all had many hardships and i can't say that one had a life more painful than others. All of them were treated in a different way they found painful.
I know i might have deviated from the subject of this thread, but these are my thoughts and i surely know that many of you think and feel the same. I learned many important things from naruto, from everyone of them. They seem real, don't they?
I hope you understand my point... I'm not a sentimental person, i just see the reality...I may sound like someone, a stranger, who talks about peace in the world and inner happiness =D but this is the truth..Naruto is not just a manga or anime, it's a whole world.