- When "conversing", characters have only so many different things they can say, which can lead to some hilarious conversations.
Random townswoman: Do you ever sit alone in your room and eat ice cream and think about boys?Random townsman: Yes! Absolutely!
- "Kick me" signs work in a very amusing way. The way they seem to be programmed is that people will see the sign and then run over to kick the person with the sign. Students might get kicked by their own clique members, kids will kick them, girls will run up and kick them, prefects will kick them, heck, if you're lucky, you can even get the gym teacher to run up and kick somebody with a sign on their back. Then a riot starts. It's kind of a shame that there's no way to make them and the only way you can get them is through lockpicking lockers and it's a random drop.
- Hilariously, sometimes the prefects will have a glitch wherein their AI will command them to go kick someone with a sign on their back, and as soon as they fight back, will bust them.
- Let's face it, we've all wanted to grab a prefect and give him a swirly every once in a while.
- Wedgies are always good for a chuckle, but it gets laugh-out-loud funny when you give one to a prefect immediately after he says to himself "Man, I wish someone would start some trouble!" *yoink!*
- Marbles in front of the only exit in the Boys' Dorm + Fire alarm = Instant comedy.
- Hitting someone in the low-hanging fruit is one of the joys of this game. The fact that each person has something unique to say about their bruised testes just adds more wonderful to the game.
- Bo Jackson: "Ohhh NOOOO, MY CHILDREN!"
- Juri Karamazov: "How... (Chokes) did you... (Hyperventilates) hit it?! (Screams)"
- Luis Lanna: "Ahhh! AHHH! Aw man!! My little friends! Ahhh!"
- Gordon Wakefield: "AHHH! I'LL SUE YOUR ASS IF I EVER HAVE STUPID KIDS!"
- Peanut Romano: "Oww! My johnson! Augghh!"
- Vance Medici: "OHHHH, right in the hot rod!"
- Lefty Mancini: "My girlfiend's gonna kill you!"
- Ricky Pucino: "CHEAP SON OF A- SACKMEAT!! FREAKING COWARD!! Ohhh..."
- Algernon (Algie) Papadopoulos: "Oooh, critical hit!"
- Fatty: "Ugh! oh, please, no... my legacy...."
- Melvin: "AHHH!!!!! OHH, RIGHT IN THE JABBERWOCKY! AH-HA!!!!!!"
- Cornelius Johnson: "That... is ex-CRU-ciatingly- PAINFULL!!"
- Tad Spencer: "Ooh, daddy! Ohhh..."
- Derby Harrington: "GUAHH!!! Ohhh, LORD!!! (Gasps) I have to carry on the family name! (breaks down crying)"
- Chad Morris: "My family jewels! My lineage, destroyed!"
- Kirby Olsen: "DAGH! THANK YOU, SIR, MAY I HAVE SOME MORE?"
- Edgar Munsen: "(cough) You fight dirty, AH-HOW!"
- Omar Romero: "OHHHHHHH!! ...I am tough... Threre is no pain...! OHHHHHHHHHH!!!"
- Leeroy: "UNH!! WHAT'D YOU HAVE TO DO THAT FOR?!"
- Henry (a.k.a. Clint): "OHHH! Right in the Toxic Twins!"
- Gurney: "HOLY- FUNGUS!"
- Jerry: "OOOH!! (Beat) I'll never be able to piss again!"
- Russell Northrup: "HOHH!!! ...Russell's secret place!"
- Gary Smith: "OWWW!!! You can't do that!" (Note: This is the same guy who said "You know what we do to liars, Pete? We kick them in the BALLS!!")
- Russell declaring that he "... likes to HURT people... for PEACE."
Edgar Munsen: "Alright, one question: How are we going to stop a load of kids from beating the crap out of each other?"Jimmy: "This is 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!"
- Then, there's Jimmy's Rousing Speech for when he's convincing Russell and the Townies to break up the school-wide brawl in "Complete Mayhem":
- If you can get hold of the data files, there's some unused dialogue in the mission Jealous Johnny. Long story short, Gord and Lola are making out, and then Gord can't figure out how to unhook her bra.
- The opening cutscene of Hattrick vs. Galloway. After Jimmy takes Galloway's scotch and leaves to track down all of Galloway's stashes around the school, Galloway immediately pulls out another bottle of scotch.
I've tried many things: Yoga, meditation, acupuncture, dubious sites on the Internet... but nothing dulls the pain like Scotch!
Hattrick: Drunk, in charge of children. What kind of monster drinks in front of children?
- Earlier in that scene, when Hattrick is chewing out Galloway for drinking on campus, this exchange ensues:
- If you go to the Boys Bathrooms, you can see a random individual smoking a cigarette. What makes this funny is when you see Algie of all people doing it, too!
- The end of the Panty Raid mission scene, when Burton says he'll claim ignorance if Jimmy's caught:
Jimmy: I won't say anything, sir. In fact, I'll make it clear that I never saw you coming out of an adult store clutching illicit magazines.
- The intro cutscene to the mission "Weed Killer", where Dr. Slawter wants Jimmy to destroy a plant given to Derby.
Dr. Slawter: There are two sides to biology, boy. Life... and death. Do I make myself clear?Dr. Slawter: Not the boy, boy! The plant, boy! Kill the plant!Jimmy: Oh... Right.
- Because of authorities immediately going after you if you hit a small kid, you're unlikely to hear it, but when knocking out Pedro, he tends to spout a Non Sequitur Thud.
What does "Call me Ishmael" even mean...?I'll get a job in the morning, mama...Pancakes...? Where are the waffles...?
- There's a mission in which Ms Philips requests Jimmy to bring her a few things (some perfume, a dress, and a necklace) to prepare herself for a date. Jimmy thinks she was having a date with him, and ends up quite disappointed when Mr Galloway shows up.