Sideways Stories from Wayside School
A wacky and occasionally surreal classic.
It’s Wednesday and that means another chapter book review is in your inbox. If you know anyone who would like to have this be part of their Wednesday, please forward this to them (and someone did forward you this email, you can subscribe for free at this link.
Now on to…
The Series: Sideways Stories from Wayside School
The Author: Louis Sachar
The Illustrator: Joel Schick or Tim Heitz, depending on edition (the books make no reference to characters’ race/ethnicity, but Schick’s illustrations show an all-white school while Heitz’s are more diverse).
The Review: Alright, I think I can be objective here, but I’ll start with the caveat that the first two of these were seminal works for young me. The first three were written in the 90s, and he added a fourth, Wayside School Beneath the Cloud of Doom, in 2020 when many of us felt like we lived under a cloud of doom (Not like now! Everything is great! [screams internally]).
Um, anyway, these are funny, charming, and subversive in a way I still enjoy.
The books are episodic tales about the kids who go to school on the 30th story of a 30-story building with no elevator. The first book focuses on one kid per chapter, and the subsequent ones have a similar format with a bit more flexibility. The latter two have more of an ongoing plot than the first two, but none are plot-driven in the normal sense – each chapter is its own little story.
The stories are wacky and slapstick, but still have an emotional backbone that comes from the kids’ friendships and the mutual love between them and their teacher, Mrs. Jewels.
What these books do really well is integrate surreal elements in a way that just feels fun and silly. There’s a chapter where the paragraphs are in reverse order. There’s a floor of the building that does not exist. At one point, each kid has an associated flavor of ice cream that tastes like their personality, except no one can taste their own flavor. These books get conceptually creative in ways that few chapter books do.
Problematic stuff: I would occasionally edit out some of the insults (what’s your parental tolerance for “Get off my case, buzzard face!”) that the kids hurl at each other, and there is a little bit of boys vs. girls stuff I’d try to pass over, but otherwise they’re a pretty smooth read.
In the third book, Wayside School Gets a Little Stranger, the kids get a succession of teachers while Mrs. Jewels goes on maternity leave, and at points the teachers become more villainous than I’d like. The books have an enjoyable question-the-system strain throughout, but in the third one it switches more to “Mrs. Jewels: good, all other teachers: evil”. Each teacher is dealt with in a very satisfying way, but I found the earlier books, particularly the second, Wayside School is Falling Down, more satisfying and the anti-authoritarian sentiment subtler and more agreeable.
In that same vein, the principal is named Mr. Kidswatter (I would read it like it was a normal last name, and I don’t think my kid figured it out) and he has a little more of a role in the third book. He’s a shouty buffoon, but he doesn’t get in the way of the stories too much.
I keep bringing up the subversive strain in the Wayside School books. What exactly am I talking about?
The best way to illustrate that is through Myron’s story in the second book. Myron feeds cracker crumbs to a pigeon outside his window, and eventually realizes that the pigeon must think he lives in a cage: he sits every day in an enclosed space, and isn’t allowed to do something as basic as sit on the floor.
That feeling leads on a journey where he meets a mysterious trio of men in suits (they show up periodically throughout the books, always know exactly what is going on when no one else does, and are never explained) who tell him that he can be free or he can be safe. He can play by the rules and be protected by them, or he can be like the pigeon – free to do as he pleases, whatever the consequences.
Myron chooses freedom. Then he goes back upstairs and sits on the floor, and Mrs. Jewels can’t do anything about it.
The book doesn’t make a big deal of this outside of Myron’s chapter – we get occasional reminders that Myron just does his own thing – but the author is pretty clearly on Myron’s side.
All that said, the rest of the kids are normal enough – they just happen to go to school in a place where absurd things happen and stuff occasionally gets a little surreal.
If you’re a play-it-safe book selector, these probably fall outside of truly safe, but my kid loved them all, and I’d say they held up from my childhood through multiple readings.