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I think I actually cried too when I watched this episode (oh come on I was 7)
This is when Tyranitar is being electrocuted while wrapped up in one of the Pokemon Poacher's Traps
Didn't enter the first round but I would like a shot at this
Image is tiny as I took it from serebii :[
Spoiler:
The episode where Pikachu meets with a group of other Pikachus and at the endd of the episode Ash tries to release him. I don't think this picture captures the whole scene but it was really sad.
Why? Because her father was taken by the Unown, she thought she could never see him again, she doesn't have a mother anymore, and Delia is all she has left in this world besides Entei and this image shows their bond. Even though Delia is under the spell of the Unown, her motherly instincts shine through and the image almost pretty much says that she'll protect Molly and along with Entei, they'll be fine. :3 (from serebii btw since we're showing sources) -was going to use one with Entei but that didn't look as good so yeah-
...
I love that movie so much. XD; Also, imo, I don't think Ash/Pikachu moments are as tear jerking because... they're so common, as opposed to other moments in the anime that can actually bring out emotion, rather than always being with the title characters. But that's just why I chose this, so yeah.
we can use the first 5 movies??? great!
Celebi: Voice of the Forest
This is the scene, when Ash and others think that Celebi has "died", despite everything Ash and Sam (Prof. Oak) do to try to save him.
Spoiler:
This was the first time i actually cried while watching pokemon.