[Mac Sirloin]

The Iron Giant, when he loses control. Again when he saves the world. If I was hydrated, some sniffles at the final shot.
The bit in Wall-E that is specifically engineered to make you sad as fuck.
The first time I watched the MGS5 Trailer (The one with the song by Garbage) I started crying. I was in a really weird place then though, and haven't reacted that way since.

The climax to pretty much every Ghibli film, with a few exceptions. I once cried through what felt like the entirety of Ponyo when I caught it some afternoon I was intoxicated. Not sad tears, either. Sometimes really gorgeous animation just makes me a blubbering mess.

In the Sonic OVA (Which I haven't watched in a very long time) Metal Sonic lets himself die for no reason in particular. This is in and of itself not necessarily upsetting, but the manner of his robot death, which is vividly presented as a horrific boiling, strobing disaster throbbing into nothing at the edge of a lava pit, was super unsettling and disturbing and yeah I basically go into hysterics whenever I see that .gif of ASIMO falling down the stairs.

When I was very small, I watched Digimon after school every day. In the second season of Digimon there's this antagonist called Puppetmon. I thought Puppetmon was awesome and the whiny kids were idiots (except for Tai. obviously). I was so upset when he got deleted my sister drew up a comic outlining how no, he did not die, he actually turned good and became my best friend.