- Ensemble Dark Horse: Mark Millar
- Family-Unfriendly Aesop: 20, 21, & 22. Eric, Eric, & Eric: You should lie so that you don't feel scared/nervous.
- First Installment Wins: While the later two books get some love, the first book is considered the most memorable.
- Genius Bonus: Wayside School is Falling Down states that Albert Einstein didn't wear socks with the implication that socks make you less smart. It seems like an example of the books' nonsensical humor but Einstein did prefer not to wear socks.
- Harsher in Hindsight: Crossing over with Values Resonance - Miss Zarves keeps her 'class' on Floor 19 trapped with memorizing the dictionary as busywork, and an endless cycle of pop-quizzes and grades. A standard (if exaggerated) little-kid fear back in the '70s, but it gains a lot more teeth in the age of No Child Left Behind and schools across the nation essentially turning into test-taking, grade-spewing factories.
- Hilarious in Hindsight: Paul and Leslie are implied to have some form of a relationship potential down the line. Then an episode of Kitchen Nightmares features a couple named Paul and Leslie running a restaurant with each other.
- Moral Event Horizon: In Wayside School Gets a Little Stranger, Mr. Gorf uses his third nostril steal the kids' voices. He crosses it by using Rondi's voice to tell her mother how much she hates her. He does the same to Joe's mother and would have called Leslie's as well had Miss Mush not interfered.
- Ms. Nogard almost crosses it when she contemplates throwing Mrs. Jewls' newborn daughter out a window. Keep in mind that they're thirty stories high. Thank God she listened to the baby's thoughts before she could do the act.
- Tastes Like Diabetes: The "Love and a Dead Rat" chapter in the second book. Even the dead rat can't stomach 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.
- They Wasted a Perfectly Good Plot: In Falling Down, Myron gets total freedom but has to give up safety in exchange. While the rest of the book contains numerous parts where Myron just gets to do what he wants instead of having to take the tests or lessons the other kids do, we never get to learn what kind of safety he gave up, as nothing bad ever happens to him.
- 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.
- Todd. He gets sent home early every day, even when he's not doing anything wrong. He's more horribly unlucky than he is a troublemaker.
- Jerkass Woobie: Miss Nogard. Seeing as she gave up on all love and joy, can you blame her? In her introduction story, the way her heart was utterly shattered was outright tragic. She's more a victim if anything. She makes a HeelFace Turn thanks to Mrs. Jewls' newborn daughter and Louis showing her The Power of Love.
YMMV / Wayside School