Dan’s Top 100 Everything: #18 Wayside School Trilogy


The Wayside School trilogy of books is, as far as I’m concerned, a seminal masterpiece of comedy and kidlit. They operate on a surreal, childlike level of logic that still speaks to my brain today.

More than that, the Wayside School books are honest portrayals of the confusion and paradoxes involved with being a child. As I grow older and the many sensations that are part of being a kid grow more and more distant, I value these books more, because they’re among the few stories that rekindle my memories and emotions of my youth.

I should also reiterate that the books are just really freaking funny. I often laugh out loud when I read them despite the fact that they’re aimed at kids. A good example of this sense of humor: The opening chapter of Wayside School is Falling Down makes me crack a smile every time.

I’ve written full reviews of the two books for my wife’s site, Readers By Night, so I’m just going to link to them here.

Sideways Stories from Wayside School (1978)

There’s no question that Sideways Stories from Wayside School is a silly, sweet book, but it’s also something greater. It’s archetypal and allegorical, a commentary on things like authority and conformity and the innate goodness of people and a bunch of other big ideas. Some of its stories are little more than half-baked jokes; others are dark and surreal tales. But this collection of 30 short stories adds up to a brilliant and hysterical gem for the slightly off-kilter kid inside us all.

Wayside School is Falling Down (1989)

Eleven years later, Sachar released its sequel, Wayside School is Falling Down. And this is a first-order sequel, a book that retains the spirit and energy of the original while expanding and refining its world. The second book in the Wayside series is more fully formed and polished than the original. There’s a drawback to this polish, too; some of the less developed stories feel a little bit disappointing where they felt like part of the slipshod charm in Sideways Stories. Still, the brisk format of 30 short stories is intact, which means it’s never too long before you’re sucked back in with some great little joke or little story.

Wayside School Gets a Little Stranger (1995)

I haven’t written a review yet (it’s near the top of my to-do list so that this article can be more complete), but here’s the short version: though A Little Stranger is still funny and charming, it’s easily the weakest of the trilogy. Many of the stories run for multiple chapters, which sucks some of the carefree attitude out of the book. And the focus on substitute teachers instead of students fails to yield the same comic dividends. But there’s still quite a bit to love: Some of the stories are hysterical (an elaborate “who’s on first” type gag about students’ pets might be my favorite), often going in unexpected places. It’s worth reading, but it’s a bit of a down point.


Dan and Brian from Earn This now have a film review site and podcast:

The Goods: Film Reviews

The Goods: A Film Podcast

Available on Apple Podcast, Spotify, Stitcher, and more.

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