Whether it was in a movie, in a game, in a book, or even in real life--*gets punched by mechanical fist and slams onto ground*
French narrator from Spongebob: "2 owehz laytehr..."
*Gets back up* Proceed.
My picks:
Optimus Prime, Transformers: the Movie (1986)
Cosmo, Sonic X (The Japanese version, guys)
Brooks, The Shawshank Redemption
Augustus, The Fault In Our Stars
Cortana, Halo 4
My cat, who died in 2010
Robin Williams
I may update this list later.
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The movie: A Bear Named Winnie. First (and so far) only movie I have ever cried from. Gosh, I hate when bears die :(