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- Many fans of the game complain about how easy the boss battle with Gary is. It makes sense if you think about it, though. Despite Gary's speech, he never really planned on actually fighting Jimmy. He thought Jimmy would have been expelled (which he was) and/or the whole school would have turned on him (which they did, for a time). He never expected the drop-outs to help Jimmy take back the school again. So he panicked, turned the school into a battleground, tied up the principal and planned to blame it on Jimmy but it backfired.
- A lot of Gary's manic behavior and his less than satisfactory reasoning for manipulating everyone. He states twice that he's not been taking his meds. The mission before he betrays Jimmy, you see him frantically talking to himself. His betrayal and eventual taking over the school can be explained by Gary literally being out of his mind.
- During the bossfight which concludes chapter 4, once all Ted Thompson's defenders have been eliminated, the fight turns to a 1 VS 1 brawl against him, at which point he's defeated after being hit exactly one time. It can seem strange that an athletic teenager wearing football protections is beaten so easily by a much shorter boy, but, before this, you had to defeat the defenders surrounding him by throwing explosive footballs at them. Given there was a dozen explosions around him right before the final sequence of the bossfight, of course he turns to be disappointingly weak: he probably suffered from a mild concussion.
- English and Math classes both consist in a time-limited quizz, but succeding in Math requires a much higher score than in English. Since Mr. Galloway is a very nice and lenient man (in the opening cutscene of one of the English classes, he notes that some students are sharing the answers to the test, and congratulate the students for such a demonstration of team spirit), while Mr. Hattrick is a jerk and a bully as well (Galloway's alcoholism is strongly implied to have been caused by years of abuse from Hattrick), no wonder that Math is a lot harder than English.
- In the beginning of chapter 4, Jimmy asks Algie to help him join his fellow Nerds, in order to get help to defeat the Jocks clique. Algie refuses, saying that Jimmy himself is sometimes unpleasant to them, and that he already called him "Pee Stain". It could be a clue about Gary keeping to spread rumours: think "The Eggs", in which he turns the Preppies against Jimmy with this method (by spreading rumours about Jimmy telling that Tad is heavily inbred).
- Despite being supposedly fired over the course of the game both Mr. Hattrick and Mr. Burton are apparently still teaching their classes if the player waits to finish the Math and Gym classes respectively afterwards. This makes sense however as Bullworth is stated repeatedly to be the worst school in the country with a reputation to match. It's highly likely those two haven't been officially fired yet simply because there's no teachers willing to actually work at Bullworth to replace them with.
- Bullworth Academy is a private school. Think about that. People pay for their kids to suffer through that school. Or it might imply that public schools are even worse.