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.
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!*
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.