The first time Naruto cries, he is alone. He does not understand why they hate him, or why they hurt him. He does not understand why he is alone, when all the other children have parents, sibling, friends. He does not understand why, even when people are not mean to him, they are afraid of him. He does not understand, so he cries.
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The second time Naruto cries, he is mostly alone. He is watching all the kids from his class, all of whom graduated, being congratulated and hugged by their parents. He is watching the kids he has spent the year with celebrate, and he is not with them. He is used to watching the other kids—in class, at recess, during training sessions—because he is never with them, and is never part of them. He is always watching, so he cries.
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The third time Naruto cries, Sasuke is with him. Sasuke is dead; he died protecting him. Naruto is not used to being protected. He doesn't like it. Naruto is not used to caring about someone, or having someone care about him. He is not used to worrying, or grieving, or needing someone else. He is not used to the pain, so he cries.
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The fourth time Naruto cries, Sakura is with him. Sasuke is gone, and Naruto failed to save him. Sakura says she is not angry, but Naruto thinks she hates him. He made a promise to her, and he failed to keep it. He made a promise to Sasuke, and he failed to keep it. He made a promise to himself, and he failed to keep it. He failed, so he cries.
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The fifth time Naruto cries, there are a lot of people with him. Gaara is dead, and Naruto has failed again. He was just like him; they were both hated, feared, and shunned as children. He was just like him; they were both seen as monsters, weapons, and tools. He was just like him; they were both hunted. He was just like him; they had felt the same pain, the same fear, the same insecurities. He was just like him, so he cries.
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The last time Naruto cries, he is alone. He is dying, and he will not get to say goodbye. He is too far away, and they will not find him in time. He will not get to say goodbye to his team, his friends, and all the people he has come to care about. He will not get to say sorry to Sasuke, to Sakura, to Jiraiya, and to all the people he has let down. He will not get to say "I love you" to Sakura, Kakashi, Tsunade, Sai, Konohamaru, and all the people he has come to see as his family. There are so many things he will not get to say, so he cries.
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Wow, I have absolutely no idea about this one. I was in a really good mood, just reading fanfiction and listening to happy music, and then all of a sudden I had this insane idea. I haven't had inspiration like this in a long time. I hope it wasn't too painful to read.