I haven’t cried until Anohana after watching some part of it for a couple times. Sometimes whenever the episode gets to an emotional part I just sit like a stone wall.
These days most Anime get me (with exceptions being there), but I don't completely cry for some reason, it's like tearing up a bit and then watch it again as if nothing happened.
The anime which actually made me cry was Kimi no Suizou wo tabetai (I want to eat your pancreas)
Small spoiler alert below if you are going to watch the movie in future.
The part where I cried was the main Haruki asking "Are you really dying" and Sakura replied "Sure am" and that with a bright sweet smile, so yeah it got me, and I started crying, for real. It was midnight and I started weeping crazily.
You can check the anime here on MAL. It's pretty well known but just incase if anyone didn't knew
one of the last episodes in kaguya sama love is war, there is a story about ishigami’s past and it’s really sad. probably the first time i cried about an anime. also many deaths in jojo were upsetting.