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  • It's pretty clear that Jimmy loves his mom, despite the tense interaction they have in the opening cinematic. When Gary insults her by saying she made her "living on her back", Jimmy goes berserk.
  • Despite treating Petey like crap for pretty much the entire game, Jimmy proves at the end that he truly does care for him: Upon defeating Gary and untying Dr. Crabblesnitch, the latter tells the former that Petey should be the school's Head Boy (previously held by the now-expelled Gary), to which Jimmy agrees. Aww.
    • Add to that their final words to each other:
    Jimmy: Now, about that letter to my mother...
    Crabblesnitch: What letter?
  • Jimmy in general is this - He's quite a Jerkass who often acts out for the sake of payment, though he has plenty of moments where he goes out of his way to help people, including:
    • Helping Brandy destroy lawn gnomes that she feels are a mockery of her dwarfism.
    • Helping Mandy cover up the embarrassing posters of her Earnest made.
    • Helping Beatrice get her papers back from Mandy.
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    • Helping Zoe get revenge on Burton for getting her expelled for reporting him for sexual harassment. Then getting her expulsion lifted.
    • Trying to extend an olive branch to clique leaders he has beaten, who weren't completely jerks.
    • Helping Galloway cover up his alcoholism.
    • Helping Edna get a date. note 
    • Last but not least, the whole reason for his crusade earning the respect of every clique at school, to stop the bullying.
    • It's optional, but just listen to Eunice's voice if Jimmy put the moves on her. It obviously makes her day.
  • At the very beginning of the game where Gary shows Jimmy around Bullworth Academy, they come across Eunice, the only fat, slightly unattractive girl in the school. Gary says "Oh, here come that weird chick Eunice; let's have some fun with her." It would've been so easy for Gary (and in turn, the writers of the game) to call her "that fat chick", but in a display of taking the high road and not choosing to fat-shame, they have Gary say "weird chick" instead.
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