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  • Complete Monster: Mrs. Gorf and Mrs. Nogard until her Heel Face Turn.
    • Mr. Gorf also seems like one, especially since he stole the voices of a married Scotsman, an old lady, and a dog for no explained reason.
  • Moral Event Horizon: Mrs. Nogard uses her Telepathy to subtly manipulate everyone into feeling as miserable as herself. But as cruel as she is, she doesn't come that close to pure evil until she decides to "accidentally" drop Mrs. Jewls' newborn baby out the 30th floor window. Luckily, Louis and the baby herself save her from going through with it.
  • They Changed It, Now It Sucks: What some readers said after reprints of the books received illustrations that looked more abstract than those used from the 1970s through the '90s.
  • Toy Ship: The books are full of them. Jason and Allison is probably the most prominent but others include: Paul and Leslie, Dana and John, Calvin and Bebe, DJ and Kathy, Terrence and Rondi, Ron and Deedee, and Todd and Joy. A possible canon example is Mac and Nancy, a girl from another class. She's his friend in the first book but is said to be his girlfriend in the second. It's unknown if that's meant in a romantic sense but she does carry his books.
    • In Sideways Arithmetic from Wayside School, Word of God confirms that Jason and Allison are secretly in love with each other.
  • The Woobie: Miss Zarves in Gets a Little Stranger, in which she is upset over being unnoticed by the rest of the school despite loving her job and students.
    • Allison definitely needed a hug when everyone stopped noticing her, until she got to the nineteenth story.
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