Most Heartbreaking Moments in Anime?

I just watched Violet Evergarden movie. I knew the anime was a tearjerker, but for some reason I wasn't prepared for that last 30 minutes. Dang that was so sad.

https://i.ani.me/0382/8296/1000009613.jpg So the Red Circus conflict in Spy Family wasn't exactly the most sad depiction of everyday people being radicalized because of a personal stake in a global conflict that doesn't care nor is remotely changed in the slightest despite the legitimate reasons those persons might have had. That being the case, I did admit to getting slightly teary when the leader of the group was having PTSD of his daughter's death during the bus jacking. Admittedly I was also surprised that he managed to walk away without getting killed. When he was surrendering after Anya and her teacher managed to talk him down I fully expected the Security of State to simply shoot him on sight. Kind of refreshing the narrative chose to end with him being taken alive. Not to say the government won't black bag the man in a ditch off screen, but it did subvert my expectation.