- The Public Relations Representative's fight is very upsetting, as the poor Cog was driven mad from loneliness and there's no real way to help him. To drive the point home, one of his quotes when he defeats a Toon is begging them to not leave. Even his friendship-declining quotes are sad.The Public Relations Representative looks taken aback: "What? You want to- want to be- I can't- I can't- I can't ERROR"
- Rainmaker's battle. She's a Tragic Villain who holds nothing against the Toons and wants to befriend them but is forced into fighting them. In the second half, her expression changes so that she appears to be on the verge of tears while you continue fighting her. Her dialogue and the Sad Battle Music also contribute to it being a much more depressing fight than usual. Thankfully, you can spare her on the last turn to end the fight on a slightly happier note.
- The Chainsaw Consultant is another Tragic Villain like Rainmaker above, being forced to fight Toons against his will. This time however, it's literal due to his Personality Override which randomly and forcefully turns him into a Laff thirsty psychotic maniac who abuses and fires his employees like they're on a conveyer belt assembly line. To say the least, he despises each time where it activates, and he can only fight back against it but so much to keep from going too far off the deep end. Even after you defeat him, he can only apologize to you before you have to leave him to lament his current position.
http://tvtropes.org/pmwiki/pmwiki.php/TearJerker/ToontownCorporateClash
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