Bully Hunter: He's particularly disgusted with how lower caste students prey on each other, rather than face the might of the preps, jocks and others. As he said to Russell, "There are bunch of idiots in this school who need a good beating and you're picking on the few who don't."
The Casanova: Given that he's able to get the attention of 8 girls by the end of the game, and six guys too. (His mojo fails on the art professor, however.)
Clint Squint: It's a wonder he can even see though those slits.
Combat Pragmatist: Jimmy can explore many ways to take down an opponent, ranging from a simple punch in the face, to using a freaking bottle rocket launcher to paste someone from a distance.
Covered In Scars: Jimmy's dome is marred by a few scars, which disappear if you grow his hair out..
Cultured Badass: Art classes show that Jimmy has a surprising gift for oil painting.
Custom Uniform: For some reason, only he and Petey wear bright blue vests over their uniforms. The Nerds and the Non-Clique Students respectively wear kelly green and dark teal sweater vests, and Gary has a unique teal vest. The other cliques don't wear school sweater-vests.
In beta screenshots, the Non-Clique Students wore blue vests the same color as Jimmy's. It's probable that they were switched to dark teal to make Jimmy stand out more.
Cutscene Incompetence: Whenever Gary's around, Jimmy seems to lose the ability to do anything besides clench his fists, scuff his feet, and huff. This could be justified by Jimmy's slight twinge of pity and remorse for losing Gary as a pal.
There's also a scene where Jimmy sees a pack of Townies and claims there's too many of them for him to beat, although that wouldn't be horribly difficult for a player to do.
Deadpan Snarker: Hopkins' brand of humor, which is helped enormously by him being the Great Stone Face of Bullworth Academy. He especially enjoys running fast ones past the Headmaster (criticizing his dress sense among other things), even during his expulsion proceeding.
Crabblesnitch: Very droll! A comedian to the end. Well, you are going to have to take your comedic talents elsewhere.
Disappeared Dad: No mention is made of his birth/biological father, only that he has had many stepfathers.
Dude, Where's My Respect?: By becoming the school's most powerful leader, he unwittingly becomes a whipping boy for everything that goes wrong. Jimmy tries his best to maintain order, but he's rearranging the deckchairs on the Titanic by that point.
Good Is Not Nice: He's stingy with kind words and not particularly philanthropic; he'll protect you from bullies in exchange for cash on the nail. Very rarely does he act out of the goodness of his heart.
He Who Fights Monsters: Jimmy originally set out to quash the bullying. However, the popularity goes to his head and he becomes a pale copy of Gary, even inheriting the latter's punching bag Pete .
High School Hustler: A hard-assed incarnation, though you'd need to be to survive in a place like Bullworth. He's also less adept at it than Gary, resorting to fisticuffs rather than flattery and lies.
It Runs in the Family: Jim scores with an absurd number of girls throughout the game. It must be in the genes, seeing as how his mother is a serial divorcée.
Knight in Sour Armor: He shows utter disrespect to pretty well everybody, but he ultimately does lay everything on the line to safeguard Bulworth. He also shows a softer side to the ladies: When Mandy breaks down at seeing voyeuristic posters of her that the Nerds wallpapered all over the town (with Jimmy's help), Jim tries to console her; then, seeing it did no good, he leaves to deface the posters before the school board sees them.
Deal with the Devil: Gary makes the same sales pitch to everybody when tempting them to the dark sid— er, his clique. First he promises to divide Bullworth between them 50-50, then pretends to assume a strictly advisory role. Earnest is especially susceptible thanks to his own naked lust for power and messiah complex.
For the Evulz: Gary represents abuse of power for its own sake, making him the ultimate bully in Jimmy's eyes.
Freudian Excuse: Half way through the first chapter he excitedly stated that he was off his meds. His behavior implies that he may also suffer from Schizophrenia. These two factors play a large role in humanizing him.
Jimmy: You are sad, man. Gary: I may be sad, but I run your world, moron! And don't you forget it!
High School Hustler: Deconstruction of the Ferris Bueller archetype, expertly manipulating students and staff for his personal gain. As Bully demonstrates, only a psychopath would be this good at it.
I Win Because You Don't: Gary gloats about this in "Complete Mayhem", explaining that if Jimmy loses against him, he's just another bitch — but if the Head Boy is beaten up, Jimmy will be in even worse trouble. This winds up being moot when the Headmaster overhears his entire speech.
It Amused Me: When Jimmy asks, "Why'd you do it?", this is his response. The fact that Gary took the Principal hostage and turned the school into a warzone, yet is still Head Boy makes his victory all the sweeter; in Gary's mind, he's proven his superiority over the "little people."
Jerk with a Heart of Jerk: Gary comes off like a immature braggart in Chapter 1, forming his own clique with Jim and Pete while simultaneously claiming that friendship is just illusory. It later turns out Gary isn't hypocritical or putting up a tough exterior: he really is that evil.
Laser-Guided Karma: After being expelled in place of Jimmy, NPC chatter reports that he's skulking the belltower like the Hunchback of Notre Dame (though this is probably an exaggeration) and - more likely - living in the trailer park with the Townies.
Let No Crisis Go to Waste: Once Jimmy becomes Bullworth's King, Gary ratchets up the chaos by letting rats loose in the library, destroying the Preps' antique trophies, and setting the gym on fire. Each incident is laid at Jimmy's feet since he promised peace in our time.
Let's You and Him Fight: Gary couldn't conquer the cliques with his fists, and needed a brute like Jimmy to lead them. Once Jimmy becomes the King of School, Gary secretly arranges for his expulsion, leaving the leaderless and confused gangs in need of a hand: Gary Smith's.
Loners Are Freaks: There's a reason we rarely see Gary following the fight in the sewers: He spends nearly all his waking moments in the dormitory, making plans. In doing so, however, he missed out on all the action Jimmy was having around town; adventures that, in theory, Gary could have participated in, instead.
"While you were off wasting your time with whores like Lola, I was in the dorm, planning. While you were racing bikes, while you were playing at the carnival like a child, my plan was coming together!
Misanthrope Supreme: Among his pet hates are his parents, his school, "small" people, and western civilization.
Motive Rant: An extended one in the finale, which proves his undoing.
A Nazi by Any Other Name: As his Halloween costume suggests, Gary is a non-too-subtle parody of Adolf Hitler (right down to the haircut). A hysteric xenophobe, possibly suffering from some form of parental neglect or mental illness, who comes to power by way of a series of extralegal maneuverings, sets fire to Bullworth's gym in his very own riff on the Reichstag, and talks constantly of ruling his own evil imperium someday.
Non-Action Big Bad: He's a whiz at manipulation and backstabbing, but a in a straight fistfight his bark proves to a lot bigger than his bite.
Not-So-Harmless Villain: Somehow, he was apparently able to convince all of the cliques to trust him, although most, if not all of their leaders show open disdain for Gary.
Sanity Slippage: Becomes more excitable (and erratic) after going off his meds. "I should've gone off those pills a long time ago!"
Self-Fulfilling Prophecy: Jimmy eventually does take over the school before him, just as he suspected — which wouldn't have happened if Gary hadn't accused Jimmy of trying to taking over.
The Social Darwinist: Frequently proclaims his contempt for "weak people" and the necessity of betraying your friends first. He's also under the delusion that everybody in the world thinks just like him, including Jimmy.
The Sociopath: Textbook case. He's also unable to grasp the difference between holding total power over others and real friendship.
Villain Cred: Gary Smith is renowned in the cliques for his sadism, though Jimmy doesn't quite believe it. There is also a false but persistent rumour that Gary's a werewolf.
Villain with Good Publicity: Crabblesnitch lauds him as a role model who isn't afraid of being an "unpopular leader." Doubtless this was his interpretation of why the cliques all loathe Smith, yet seemingly follow him without question.
Jimmy: Oh, congratulations. You're "smarter than me"! You hate everyone and everyone hates you! Genius!
Your Mom: The last mistake he makes before Jimmy kicks his ass is insulting Jimmy's mother.
Almighty Janitor: Pete is considerably smart, possibly even rivaling Gary. His advice to Jimmy proved to be valuable in his campaign against the Preps and the Nerds, and he also zeroed in on Gary being the one plotting behind their backs.
Ambiguously Gay: Petey is suggested to be either bisexual or homosexual because of his pink shirt, oft-mentioned virginity, and lack of friends, not to mention an excruciatingly awkward joke he makes suggesting that Jimmy would make a good male stripper. He's also a fan of Bullworth's televised swim practice sessions.
Butt Monkey: Mocked by nerds, stuffed in a garbage can on Halloween night, and receiving no end of torment from his supposed 'friends'. He later admits he put up with Gary and Jimmy's abuse because it was better than the alternative.
Cool Loser: In his own words, he's too cool to be a nerd, but not cool enough to fit in anywhere else. He mainly gets no respect because he never stands up for himself or shows any backbone in a setting where even the nerds will often push back when bullied.
Embarrassing Nickname: He really doesn't care for being called Petey, although he's too meek to do anything about it.
Loners Are Freaks: Analyzed trope, in contrast to genuinely antisocial Gary Smith. Pete's solitude is taken as proof by the cliques that something's wrong with him.
Non-Action Guy: The closest he comes to doing something action-y was during the boss fight against Johnny Vincent, where he operates an electromagnetic crane... after Jimmy knocks out every single Greaser who was in his way.
Only Sane Man: He continually tries to warn Jimmy about imminent dangers, but Jimmy neglects him more and more as his popularity increases.
Pink Means Feminine: He also wears a pink bunny suit in Halloween, but only after being forced into it by Gary. Also, his Bullworth polo appears to have been dyed in the wash.
The Big Guy / The Brute: Russell has various medical issues both stated and or rumored. His size may be the result of gigantism or acromegaly, since he mentions that Nurse Mc Rae told him he has overactive glands. According to Vance, Russell was once in a psycho ward.
Born in the Wrong Century: Some of his NPC chatter suggests he is the Marv of Bully's universe. "Russell would be barbarian king thousand years ago!"
Chekhov's Skill: Russell's hard head comes in handy for breaking down Bullworth's gate in the finale.
Defeat Means Friendship: He's the only clique leader who never turns on Jimmy after being beaten. Like the other punks, Russell will offers to be your bodyguard in free roam mode. He'll also defend you during "Complete Mayhem", later chasing off a cowardly pair of Prefects.
"GET OFF MY LITTLE BUDDY! RAWR!"
Dumb Is Good: Russell is staggeringly stupid, but nevertheless has a sense of justice, as evidenced when Jimmy makes him realize that his bullying is bad.
"Inside Russell's thick skin; big heart of warrior poet."
Eagleland: This becomes evident when listening to Jimmy's plans for taking back Bullworth: bribe and threaten everybody to stop fighting, and if that doesn't work, Russell will kick the crap out of everyone. ("Russel likes to hurt people! For peace!") Note also Russell's color scheme: a mop of red hair, white polo shirt, and blue jeans.
Heel-Face Turn: Albeit it's not so much Russell having a change of heart as it is Jimmy managing to point his bullying tendencies in a safer direction.
Screw the Rules, I Have Money!: Russell never sets foot in the school building and is a known felon, but he lives in the posh, Preppy-dominated suburb in Bullworth Vale, suggesting that his family is well off.
Unskilled, but Strong: Usually fights by just clumsily lashing out with his fists and legs, but this is still enough to knock out a champion boxer like Biff or any one of the Jocks in only a few hits.
Warmup Boss: Russell is a dangerous enemy throughout Chapter 1, although as he never attends class, he's easy to avoid. Jimmy does have a run-in with him in the dorm hallways at Halloween. At the end of Chapter 1, Gary tricks Russell and Jimmy into fighting each other in The Hole, hoping to get him beaten up in front of the entire school. When Jimmy wins the fight, Russell, along with the other punks, becomes his friend and firm ally for the rest of the game.
Best Served Cold: With Jimmy's help, she vandalizes a portable toilet occupied by Mr. Burton, sending him careering off a cliff in a hail of feces.
Birds of a Feather: She shares Jimmy's love of vandalism and giving people what they have coming to them.
Custom Uniform: She's the only girl to have a red tartan skirt with her school outfit.
Faux Action Girl: According to the dialogue files, she's a very good fighter and quite tough for a girl. In the game itself though, all the girls share the same stats, and are the weakest characters by a large margin. Probably justified though, since Zoe couldn't have been programmed to be tough and aggressive without tinkering with the mechanics a lot.
Brother-Sister Incest: Not intended, but he can sometimes be seen making out with his sister Christy. This is because the game designers would have had to write special code to make sure they didn't, and they either didn't bother, or didn't realize - see all the confusion about names.
Stout Strength: He's tied with Norton for second toughest Greaser (behind Johnny, obviously).
What Could Have Been: Originally was going to be a part of the Bully clique. In the original PS2 version of the game, he still occasionally says "After Russell's done hitting you, I'm gonna sit on you."
The Starscream: Subverted. Damon may be tougher than Ted and he talks a bit of crap about how he'd make a better clique leader than Ted behind Ted's back, but whenever he's around Ted he's servile and repeats everything Ted says. Also justified in that Ted's the quarterback and thus the most important player on the football team and thus the most important Jock - if Damon were to try to take over the clique he'd probably just get kicked out of it.
Lovable Jock: Bo's the jock who's a nice guy by nature but forced to be a jerk by peer pressure and social expectations. He's a bit of a counterpart to Parker in the Preppies.
Unusual Euphemism: A non-double entendre one, he calls bullying and physical beatings "poundcake".
Wimpification/Flanderization: Well, there's no trope called Gayification, so the slash fandom's tendency to twist canon and selectively omit bits of it to make Kirby gayer is a combination of those two tropes.
Hidden Depths: Some dialogue of his indicates that, despite his disdain for academics, he can at least still perform half decently at them.
All There In The Voice Files: Everything we know about him was found by listening to all his dialogue lines after the voice files were leaked.
Dummied Out: Only appears in one scene in the game - the cutscene at the beginning of The Gym is Burning. Despite this he has a unique fighting style and a full set of dialogue programmed. More curiously, his dialogue set contains the same lines as clique leaders rather than regular students.
Totally Radical: In a bid to try and look cooler, he starts trying to speak (painfully) in Jive. He only stops if he's spoken to in the way he normally speaks.
Algernon: Yo, Jimmy, I'm over here! Gimme five, dude! Jimmy: Ahh, no. Algernon: Heh, heh... Yeah, well, cat, looks like your homies took care of some lames for us. Jimmy: What are you talking about? Algernon: Don't get fresh wit' your homies! Jimmy: Can you please talk normally? Algernon: This is my normal style of rapping, bro. Hoo, hoo, hoo! Jimmy: Alright. Enough. WHAT'S MY QUEST? Algernon: Ah, right. Salutations, sir James!
Screams Like a Little Girl: Especially in the mission 'Save Algie'. His cries for help when a bully gets near him could shatter glass.
Camp Bi: Jimmy can seduce him, and he seems to go gaga for boys giving him romantic presents. Talk around the school says he played a dead-on Juliet in the school play. He also has an unrequited crush on Mandy.
Not-So-Harmless Villain: As well as being a lot more aggressive than most Nerds, Thad reportedly attacked Peanut Romano a year before the game began, hitting him hard enough to break his yardstick over Peanut's head. For good measure, he managed to escape a beating from the Greasers in spite of this.
Remember the New Guy: The penultimate Townies mission has Jimmy telling Zoe that he needs to find "that Edgar kid". Prior to this Edgar hadn't even been mentioned, let alone properly introduced as a character.
Blood Knight: Nearly every thing that comes out of his mouth is either about fighting, hating Bullworth Academy, or both.