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Concerning books, A Message in a Bottle by Nickolas Sparks really did it for me. Some short story's of the history of Middle-earth are also really sad and moving. The Children of Húrin was pretty sad.

Movie-wise, Pay It Forward almost does it to me every time. The Lord of the Rings is pretty sad at the end when they're saying goodbye too.

I cried when I saw the first 3 Harry Potter movies, because they were such a disappointment. I didn't cry when Dumbledore died though.