If you missed these in the 90s, here’s the setup: Wayside School was supposed to be built one story high with 30 classrooms side-by-side. Instead, the builder got confused and built it 30 stories high with one classroom on each floor.

The stories focus on the 30th floor, taught by Mrs. Jewls (after the previous teacher, Mrs. Gorf, accidentally turned herself into an apple and got eaten). Each chapter is a self-contained, bite-sized story about a different student. There is no 19th story. There is no Miss Zarves. (Except there kind of is, but we don't talk about that).

It is essentially "sketch comedy" in book form. It’s weird, it’s illogical, and it treats children like the intelligent, chaos-loving humans they actually are.

We talk a lot about "brain rot"—that over-stimulated, low-substance content that kids consume on TikTok or YouTube Shorts. The reason that stuff works is because it’s fast, unpredictable, and leans into "anti-humor."

Louis Sachar was doing this decades ago, but with actual literary merit.

Kids love Wayside because it doesn’t talk down to them. It’s not a "moral of the story" series. It’s a "the substitute teacher is actually three cows in a trench coat" series. For a kid used to the rapid-fire pacing of Roblox memes, the short, punchy chapters in these books actually hold their attention.

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This is the entry point. It introduces the 30 students of the 30th floor. You meet Todd, who always gets sent home early on the kindergarten bus; Sharie, who sleeps through class but is the best student; and Myron, the best class president who only served for a day. It’s foundational reading for any kid ages 7-11.

In my opinion, this is the strongest in the series. The humor gets a bit more sophisticated and surreal. There’s a chapter about a "dead dog" that is actually just a very smelly dead rat in a series of overcoats that is peak Sachar. If your kid liked Diary of a Wimpy Kid, they will find this significantly funnier.

The third book leans into the "substitute teacher" trope. When Mrs. Jewls goes on maternity leave, the replacements are... problematic. One can smell your thoughts, and another collects voices in a jar. It’s slightly creepier but still firmly in the "fun-weird" category.

Sachar released this one in 2020 after a 25-year hiatus. Remarkably, he didn't lose his touch. It deals with a giant "Cloud of Doom" hanging over the school, which feels like a very apt metaphor for the general anxiety of the modern world, yet it stays silly.

There was an animated series on Nickelodeon in the mid-2000s.

The No-BS Take: It’s fine. It’s not the books. The books are a 10/10; the show is a solid 6/10. It turns the surrealism into more standard "wacky cartoon" tropes. If you have a reluctant reader, letting them watch the show might get them interested in the world, but the magic of Wayside is really in the prose and the way Sachar plays with the format of a book.

Check out our guide on the best book-to-screen adaptations for elementary kids

Recommended Ages: 7 to 12

Honestly? There’s very little to worry about.

If you want to use Wayside School to start a conversation about digital wellness (without being a buzzkill), try these prompts:

Learn more about how to encourage independent reading in the digital age

We are living in an era of "Brain Rot" where content is often loud, fast, and meaningless. Wayside School is the perfect antidote because it matches that energy and "randomness" but requires the brain to actually do the work of visualization and comprehension.

It’s a classic for a reason. If your kid is stuck in a loop of Skibidi Toilet or MrBeast challenges, toss a copy of Sideways Stories from Wayside School their way.

It’s unhinged. It’s illogical. It’s exactly what they want, just in a much better format.