Always the last episode of ouran host club
The Samurai X OVAs.
Pretty sure it gave me mental illness. Kenshin was my first husbando and they did him so dirty.
There are actually a lot of them, I get pretty emotional
Oh man those Samurai X OVAs were the most depressing things I've ever seen as a kid. I think they legit changed my perception on life. You go through all of these happy fun time episodes of Ruroni Kenshin and then the OVAs are just like a kick to your emotional balls. The animation in the OVAs is, to this day, nearly unparalleled and the writing was so top notch, but damn it is a real dream-crusher to watch.
Yeah that was super sad
Fuck, I always forget how sad that is until I get to the end
Hands down is Angel Beats. I mean here is a series that you get to know tha characters but in the final episode where they 'graduate' the character would walk off screen then the camera angle changes and you see that that person is gone.
No spoilers dick
The last one that got me was high score gal. But probably didn't help I might have been a little drunk when binging it.