Well SPOILERS! You've been warned.
Maes Hughes's Death comes in at #1 as the anime moment that made me cry. Really, known as the saddest anime death of all time theres really nothing i can say. See Fullmetal Alchemist. And cry. Also when Al got his body back...the feels!!!!
Gintoki...you ok? Raging in at #2 was Gintoki's dark past and his personality. This shocked me! Gintama, a funny anime that can make you cry at any time.
Most badass anime that made me say HELL YA!!! Kill La Kill made me go like WHOA!!! It caught me of guard when she put on the bad ass outfit.