I haven't used to cry literally in the pokemon anime, but it make me sad. For example, In the anime, some like Pokemon, I choose you, Charmander- The Stray Pokemon Bye bye Butterfree, Snow Way Out, Pikachu's Good Bye, Charizard's Buring Ambitions make look sad. In movies, the first movie in the part when the Song Brother my Brother when they are fighting is played and when Ash turned into stone. Also the Latios and Latias movie when Latios died, and my saddest moment was on the Lucario movie, especially in the ending, for example when Sir Aaron really cared about Lucario and share his final words that Lucario was more than a friend, as well in the credits when Aaron share his chocolate bar to Lucario in afterlife while the song playing. In this movie brought back my passion of pokemon when I stopped watching the anime, and that's why Lucario is my favorite pokemon right now.