Ash's Torkoal's such a cutie. It's very sensitive and cries easily, which I can relate to. I've mostly seen it cry because it was happy about something. Another emotional Pokemon Ash has is Gliscor, and he's been sensitive ever since he was a Gligar.
Well, not sure if it counts, but Rin in Regret Message breaking down crying after Len died. Now I'M crying... *sniffle*... *sniffle*... ... *bursts out crying* THIS SONG SERIES IS SO SAD!!!!
Dawn's Piplup and Ash's 皮卡丘 from Pokemon. Episode- "Memories are Made of Bliss". Ash, Pikachu, and Brock are leaving to go back to Kanto, and poor Piplup is utterly devastated because he doesn't want to say goodbye to such great friends, especially Pikachu. Watching this episode always makes me cry too.