[[folder: Sideways Stories From Wayside School ]]
* Louis tells Mrs. Jewls' students a story about children who attended a one-story schoolhouse, never got turned into apples, never ate Maurecia-flavored ice cream, etc. [[HypocriticalHumor Mrs. Jewls and her students refuse to believe a school with such "strange and silly" children exists]].
* The entire introduction, which consists entirely of the narrator attempting desperately to explain how the heck the school ended up the way it did. Especially considering the builder of the school said he was "sorry".
* In the first story, [[SadistTeacher Mrs. Gorf]] successfully turns every student into apples. Just as she's celebrating that with no students she won't need to force herself up the stairs every day, the apples attack her.
* Joe can't count, so Mrs. Jewls tries to teach him how to count... And yet Joe always arrives to the correct answer anyways ("A million, a billion, three."), resulting in the funny exchanges such as "There are four there", and he's told "No there's four!" ''SO'' many students who've gotten answers right but didn't do what the teachers wanted them to were laughing like mad at this.
* “There is no Miss Zarves. There is no nineteenth story. Sorry.” It's impossible not to laugh at the sheer absurdity, especially the first time you ever read it.
[[folder: Wayside School is Falling Down ]]
* In chapter 12 of ''Falling Down'', Jason's pencil chewing habit gets so bad he has to borrow pencils off of other students and chews them too. Mrs. Jewls' solution? Taping Jason's mouth shut. This becomes even funnier because when [[LoveInterest Allison]] laughs at him, Jason's [[TheUnintelligible speech impairment]] allows him to curse at her without impunity. Oh, and because of his big mouth, Jason has '''a lot''' of tape on his head.
** And at the end, Mrs. Jewels notes that Jason was a lot quieter than normal, and considers doing the same for the rest of the students.
* "Star bringing purple! ''Star bringing yorbel!'' ''STOP BRINGING YORBEL!'' '''''STOP RINGING YOUR BELL!'''''"
[[folder: Wayside School Gets A Little Stranger ]]
* The confusion that "Pet Day" causes for readers who don't read the list of students and pets at the end.
** And the later blink-and-you'll-miss-it CallBack in the voice switching incident.
* The introduction of elevators into the school. The principal decided that there should be two elevators: one that goes up, and one that goes down, and in order to prevent kids from playing around with them they should ''only'' be able to go in those directions. The result: the elevators are used only once, and then never again.
** The reason for the elevators- kids kept running into each other because the rule is to go up on the right side and go down on the left. Think about it for a moment ...
* When all the students were sent to different schools, Todd was sent to the worst school of all, but the narrator doesn't need to tell you what it was like -- Todd was sent to your school.
* When the kids write poems about their favorite colors, we get a few funny moments where some of the students have problems coming up with rhymes for their chosen colors -- but the prize has to go to Dana, who can't think of anything that rhymes with "pink" despite listing several words without knowing it: "I can't think. My mind's on the blink. I'm no good at poetry, I stink!" Then she complains that her pen is out of ''ink,'' and John makes fun of her and won't let her borrow his. So what does her poem end up being?
-->My favorite color is pink.\\
John is a ratfink!
[[folder: ''Sideways Arithmetic'' Series ]]
* Todd gives the correct answer to the problem, "ears+ears=swear", but then gets told to write his name under "Discipline" for swearing in the classroom.
* Eric Bacon trying to wing a geography quiz by answering every question, "Alaska", and getting "at least one" correct as a result.
* When Allison expresses concern that inviting too many boys to her birthday party would make it become too "silly", Mrs. Jewls "mathematically" confirms her concern by writing, "boys+boys=silly" on the board. Then, for the sake of gender equality, she also writes, "girls+girls=silly".
* Mrs. Jewls makes multiple attempts at trying to remember her computer's password, but each guess only delivers the message, "That is not the password." Eventually, she becomes so desperate, she also types, "That is not the password." [[spoiler:That doesn't work, either.]]