This list is not exhaustive because I can't remember all of the time anime has made me cry, these are just the ones I remember.
Big O was not watched to completion, and thus it is not being listed here. The same applies for School Days
Order is subject to change as the season progresses. This does not speak for quality of the anime, just how much I'm enjoying watching the series I'm watching.
Ranking based on what I've been able to watch thus far.
This list is from most liked to least liked for the season.
These are my top 20 anime. K-On! and Spice and Wolf include both seasons of the series because both were similarly enjoyed and I feel earned the same rankings.