Mirrai Nikki - Here with you
Naruto - Saddness & Sorrow
Elfen Lied - Lilium
Air TV - Blue Skies
Angel Beats! - Ichiban no Takaramono
Guilty Crown - Bios-Delta
D. Gray Man - Tsunaida Te ni Kiss Wo
AnoHana - Secret Base
Fairy Tail - Predestination
Rozen Maiden - Madoka
Many tears have fallen while making this post T^T. There lots of sad song but for now this is it. Shounens like Fairy Tail or Naruto Shippuuden have bunch of heartbreaking songs but I just decided to put my one favourite one :( In addition some of the songs I just fell in love with and I got a bit (BIT) resistance, so I don't fall into tears like a baby.
Post Question: What is the most saddest song which make you horribly cry?