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 cried when Forrest Gump was making a speech at Jenny's grave. It gave me some small feels, but that was the first movie I cried in, and I have watched A LOT of movies, so I was eventually going to cry.