This includes tv shows and books as well.
When I was 8 I cried during the originial transformers movie (1986) when optimus died, maximum sadness above.
Also, in the Walking dead
[spoiler] I teared up quite a bit when carl had to shoot his own mother in the head to prevent her from turning. Such an emotional scene *sobs* [/spoiler]
What has made you experience the deep well of sadness?
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All of Lone Survivor was heart wrenching, but the slide show of the real men and women who died was rough. The one video of the guy dancing with his wife at his wedding really hit me hard.