The scene where Mort is just about to confess his love for Princess Pitts and tell her that he's the one leaving dried flowers for her... and Drake Redcrest cuts in with a fresh flower. Not only did it make this troper feel extremely bad for Mort, hence the tears—but it also made me want to scream, "You BASTARD!"
The early scene where "Sunshine" explains the fight between Mr. and Mrs. Sanderson. The cut to Jenny's saddened, weary face just makes the cute helplessness of "Sunshine" all the worse. Not to mention that this scene is the first time we hear any words from Jenny other than "Ribbit"...
The final concert for the dead Funky Phil. "Just for you..." Even though it's only a Disney Death after all.
Heck, pretty much all of poor Freaky Phil's story.
No kidding. It starts out as one of the most giddily bright and funny subplots in the game, but not only the concert but when Funky's first found "dead" ("This is the worst joke everrr!"), Dinah trying to push through the whole thing and saying she wants to "do something for those kids", and the funeral after the concert ("Just let him go!") - obviously up until the realization that he wasn't dead all along, rather just shut off all made this troper cry like a child the first time she got to them. And after having beaten the game two or three times, the whole subplot does still manage to wrench her heart a bit.
" Chibi Robo! DON'T DIE!" Yeah, we find out about 30 seconds later that he's just fine, but there's just something about it that tears this troper up everytime. The sad music probably doesn't help.
Through most of the early portions of the game, the Sergeant of the Free Rangers is a Drill Sergeant Nasty who often berates his troops. Some of his men get so fed up with him, they run off in the middle of the night! But shortly after, when Chibi finally brings him the dog tags of Memphis—their lost member—his tough act comes to a head, and he totally loses it. "YOU'RE NOT FIT TO BE FREE RANGERS! ...And I'm not fit to lead you..." But tears of sorrow quickly turn to tears of triumph as his remaining men come to his aid. "YOU'RE HARD BOILED!"