Jesse is tired of failing math. When it is time for the class to get new math books, instead of getting a student's text, he gets a teacher's edition with all the answers! Instead of reporting this, he uses this, only bringing his D minus average to an A average. When Jesse competes with Penny in math for an award at school for Monster Land tickets, he, of course, beats her by one point. When he finds out Penny's sick aunt died without Penny getting to say goodbye, he starts to feel guilty.......NOT FOR LONG! He says, ""I'm goin' to Monster Land!"" Just as Jesse is about to receive his award, Mister Besser decides to give him a tough math question to show everyone his ""genius,"" which Jesse couldn't figure out, he crashed and burned, forced to give the award to Penny.

Nancy returns from her trip to Mexico ready to show off her tan and her new charm bracelet, but when class starts the kids are more interested in the choosing of the new crossing guards. When Miss Graves selects Polly and Arthur as the new guards, the kids soon discover that both her choices are a nightmare to have helping you cross the road. While Polly insists that every student learns the seven safety tips, Arthur begins charging people to cross at his corner. When Polly is almost hit by an ice-cream truck, Miss Graves learns that Arthur has been charging and forces him to use the money to buy Polly a get well present and when Arthur gets to the crossing the next day, he learns that crossing lights have been installed. Meanwhile Nancy's good luck bracelet goes missing and she tries to find out who has stolen it, only to discover that it was never stolen in the first place, it just got misplaced in her coat.

During a special assembly Jessie gets hungry and buys a packet of chocolate raisins from Arthur, but by the time the pack reaches him there is only one raisin left. As the documentary film Chinook of the North starts, most of the kids fall asleep until Vinnie sees a scene where the Eskimos all strip their clothes off. The film is immediately stopped but everybody is talking about what would have happened in the rest of the film. Back in class Jessie gets so hungry that he ends up eating a used piece of gum from under his desk, but Freddie sees him and soon the whole school is laughing at him. While Jessie tries to make people forget that he is a ""used gum chewer"", Arthur organises a secret screening of Chinook, but the rest of the film turns out to be just as boring as the beginning was and all the kids demand their money back. The next day lunch is cancelled because of a fire in the kitchen and as Miss Graves leaves the room, Jessie teases the other kids by pretending to eat more of t

Nancy is excited when she gets a Fish Book Baggie Baby from the local store, but when she gets to school she finds out that all the other girls bought the Caterpillar design and hides her own bag, embarrassed that it is different. When class starts, Miss Graves has to pick the three students to do a report on Columbus and teams up Jessie with the two smart kids, Polly and Freddie. While Polly and Freddie argue over who will do which part of the report, Jessie does everything he can to get out of doing any work at all. The next day at school, Penny arrives wearing a small fur hat and all the girls love it deciding to get them after school, but in an attempt to be more popular Nancy claims to already have one. When all her attempts to get one of the small hats fails, Nancy ends up with a really big hat that everybody makes fun of, but she ignores the insults and tries to convince everyone that it's a new trend. However when Nancy arrives at school the next day having trimmed her hat down

Arthur loses his ring, but when he goes to the lost and found office to try and find it he finds himself up against Polly who insists on him filling out sheet after sheet of paperwork and decides that it isn't worth the effort. However when Mr Besser comes back on duty, Arthur takes the opportunity to look for his ring, but rather than taking his own ring he takes somebody else's. Signing up to work in the lost and found office, Arthur volunteer Polly for a role as trash monitor and is soon taking whatever he likes from the collection. However when Miss Graves finds Arthur's ring, he demands it back and realises that what he has been doing is wrong, returning all the lost items to their rightful owners. Meanwhile Jessie becomes funny when he buys a book of 101 insults, but on the eve of Mary-Ellen's party he uses up all of the insults and is instantly booed off stage when his improvisation proves to be the unfunniest thing ever.