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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I get very close to crying at many parts of many movies, which is rather annoying. Happy parts, sad parts, funny parts, I well up at all of them. I don't think I've ever all out wept at anything recently, but still.