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Headscratchers for the film:

Why didn't Marty just stop hanging out with Bobby instead of murdering him? That would've been much easier on both of them.

Headscratchers for the video game:

  • Why does Jimmy wait the entire school year to confront Gary?
    • It's mentioned in a cutscene that after Gary stabbed him in the back, he's actually been able to avoid Jimmy. Now obviously he can't go the whole school year without being seen, but he's probably made sure that he's never caught anywhere where Jimmy can pummel him with impunity.

  • Do the prefects never attend class or take a break? All four seem to work 8:30 am to 2 am non-stop every day. No wonder they're so cranky.
    • Free roam isn't entirely accurate to showcasing the entire student population. There are many students and faculty members who only appear in cutscenes. You wouldn't know that Mr. Matthews and Neil even existed if you didn't have History and Shop classes, and that Bob attneds the school if not for one single cutscene. It's possible that there are more prefects, but they play so little a part in the story that we simply never meet them.

  • Why are there no female prefects, given that it's a mixed school?
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    • Likely none volunteer, not only are bullies quite violent but the prefects get their crotch squeezed every day by someone trying to escape them.

  • Wouldn't assaulting a police officer with an explosive weapon get you a prison sentence, or at least juvenile hall, in the real world? In fact, shouldn't Jimmy have been expelled in the first chapter in the real world?
    • The game supposedly takes place in the same universe as Grand Theft Auto, so evidently GTA cops are just really lenient on this sort of thing. (Possibly because it's such a Crapsack World that they only have jail cells for truly heinous crimes.)

  • What does "running the school" entitle? Does Gary want to be popular/respected? Even if he "rules" the school, how would he make the Cliques do anything?
    • In the end of game fight with Gary, he says he manipulated everybody because it made him feel awesome. So... that's reason enough. He's a creepy sociopath who gets off on screwing with everybody.

  • The boss fight against Ted Thompson took place on the football field in front of the entire school. The students were throwing explosive packed footballs at each other. Where the hell were the teachers?

  • The school is built up to be the worst school in the country. Yet, there are no murders, rapes (on campus anyway) or evidence of drug dealing?
    • From the students' point of view, Bullworth is the worst school in the country. You live on-campus so you're always under school authority, the faculty openly favors students with money, athletes, and those who abuse others because it builds character, detention involves forcing students to do yard labor, there's apparently no holiday breaks and no option to go home at any time, and although the authorities are on constant guard, they're utterly unable to actually prevent or control misbehavior in the school because the Prefects and teachers are easily duped by the crafty cunning of ordinary children.

  • When Gary convinces the Townies to sabotage the individual cliques (before Jimmy is expelled) and Jimmy brings the Preps proof that the Greasers didn't burn their trophies...they tell him to stuff them where the sun don't shine. Why didn't Jimmy beat the the living crap out of them to remind them who's boss?
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    • Probably because Jimmy had lost a lot of power and popularity and wasn't as intimidating as he used to be. He seemed to know that fighting them wouldn't change a thing.

  • In one of the missions in this game, you must take "risque" photos of one of the cheerleaders. A later mission has you graffiti over them after the guy you took them for starts posting them all over town (on account of Jimmy feeling bad for the girl). Not only do the authorities not help you take down inappropriate pictures of a minor, posted against her will, they ACTIVELY PUNISH YOU for trying to cover them up? Not to mention, simply ripping the posters down would be faster and felony free.
    • The authorities could be perverts who would prefer the risque photos stay up.

  • Jimmy could have avoided a lot of headaches (read: most of the events of the year) if he had just beaten the hell out of Gary in Chapter one.
    • He could have; but keep in mind that Jimmy doesn't know what we do. We might have thought of punching Gary in the face in chapter one; but from Jimmy's POV, Gary wasn't giving him any reason to not trust him aside from maybe a comment about not being on his meds. Also, he HAD just arrived and didn't have any friends to warn him. It's easy to see these things with a little hindsight.

  • The gym is set on fire. Mr. Burton accuses Jimmy of this and does absolutely nothing as a single fifteen year-old goes in and puts it out and saves several jocks and Mandy. Why did nobody call the flippin fire department?!?
    • The fire department had been called. Your going inside is because they couldn't get to Bullworth in time.

  • In the opening, Jimmy is driven to Bullworth through the underpass that later leads to the carnival. Looking at the map we can see the area behind the carnival is surrounded by cliffs. THERE IS NO ROAD THERE TO BEGIN WITH. How did they get there?

  • During one of the errands you're supposed to escort Algie to a bathroom and from one the stalls come out Pedro and Eunice. What in the world were they doing there together?
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    • Making out?

  • There's been some confusion about where Bullworth is located. Scholarship Edition's cover says that it's in New England. However, Jimmy said during "Complete Mayhem" that "It's America! We go in there with threats and bribes until we get what we want. If all else fails, we beat the crap out of everyone!"
    • New England is another name for the northeastern part of the US.

  • The number of male students at Bullworth Academy outnumber the amount of female students, so why is the girls' dorm larger than the boys' dorm?
    • They've probably packed several boys into a single room and given the girls a single room each. Of course, Jimmy gets his own room, probably because his reputation means that nobody wants to share with him.

  • Why exactly are the Nerds suddenly hostile to Jimmy at the start of Chapter 4?
    • One big recurring theme in Bullworth is that all of the cliques are jerks who need to be taken down a peg.

  • Why don't the Bullies lose respect for Jimmy after the mission "Making A Mark" like all the other cliques do?
    • Gary already manipulated Russell at the end of Chapter 1, only for Jimmy to clear things up, so he probably didn't want to try his luck again since he would only end up getting pummeled to death. Russell may be a scatterbrain, but since Jimmy told him Gary's words are bull he's probably less gullible now. There's also the fact that he (along with Pete) is Jimmy's only friend, and they have undying trust for each other.

  • If the Auto Shop is the prime hang out of the Greasers, why do most of the chapter 1 missions (where the Greasers are not involved) take place there? And why do no missions in Chapter 3 (where you actually face the Greasers) take place there?
    • Because New Coventry is actually their main hangout. And it's a far, far bigger place than some building on school grounds.
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