79 books like Sideways Stories from Wayside School

By Louis Sachar, Tim Heitz (illustrator),

Here are 79 books that Sideways Stories from Wayside School fans have personally recommended if you like Sideways Stories from Wayside School. Shepherd is a community of 12,000+ authors and super readers sharing their favorite books with the world.

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Book cover of Matilda

Rachelle Bergstein Author Of The Genius of Judy: How Judy Blume Rewrote Childhood for All of Us

From my list on retro for kids that still hold up.

Why am I passionate about this?

I was once a little girl who loved reading, and now I'm a mother who shares that passion with my kid. Over the past few years, I've been revisiting my own childhood favorites with him (it's been a serendipitous mix of work and pleasure as I was also researching a book on one of the all-time great children's book authors, Judy Blume). The novels I've recommended here are ones that seemed to spark pleasure in the most discerning—and honest—of audiences: an 8-year-old. And unlike some old books that will go unnamed, they didn't make me cringe as a 21st-century parent.

Rachelle's book list on retro for kids that still hold up

Rachelle Bergstein Why did Rachelle love this book?

When I had my son almost nine years ago, I dreamed of the day I’d be able to share my favorite childhood books with him. Matilda, which I remembered as a riveting, oddball page-turner, did not disappoint. As I read to him, we cheered for tiny Matilda to topple the mythically bad school principal, Miss Trunchbull, and we laughed until we cried when Matilda’s mother scolded her kind-hearted teacher, Miss Honey, for reading too much.

We still quote the line to each other that cracked us up: “Looks is more important than books, Miss Hunky.” I don’t know why it’s so funny, my son said at the time, but it is.

By Roald Dahl, Quentin Blake (illustrator),

Why should I read it?

12 authors picked Matilda as one of their favorite books, and they share why you should read it. This book is for kids age 8, 9, 10, and 11.

What is this book about?

Puffin Audiobooks presents Roald Dahl's Matilda, read by Kate Winslet. This audiobook features original music and sound design by Pinewood film studios.

Matilda Wormwood is an extraordinary genius with really stupid parents.

Miss Trunchbull is her terrifying headmistress who thinks all her pupils are rotten little stinkers.

But Matilda will show these horrible grown-ups that even though she's only small, she's got some very powerful tricks up her sleeve . . .

Kate Winslet's award-winning and varied career has included standout roles in Titanic, Eternal Sunshine of the Spotless Mind, Finding Neverland, Revolutionary Road and The Reader, for which she…


Book cover of The Terrible Two

Allan Woodrow Author Of The Curse of the Werepenguin

From my list on will make you laugh.

Why am I passionate about this?

I always wanted to be a writer, but as a kid, my teacher told me to write about what I know, and I didn’t know much. I didn’t know much for a long time, but eventually started writing anyway. Today, I’ve written more than thirty books for children including the popular novels Class Dismissed, The Pet War, Field Tripped, and Unschooled. I also write books under a variety of pen names, such as “Fowler DeWitt.” When I’m not writing I’m probably visiting a school or a library. I live with my family outside Chicago. 

Allan's book list on will make you laugh

Allan Woodrow Why did Allan love this book?

Miles Murphy has always been his school’s star prankster, a position he assumes will continue when he moves to a new school. Wrong. He quickly discovers the school already has a prankster, and Miles has a lot to learn about successful pranking if he’s going to keep up with his new rival. The outrageous and ingenious pranks, combined with great characters and hilarious writing, make this book by Mac Barnett and Jory John a fall-on-the-floor delight. 

By Jory John, Mac Barnett, Kevin Cornell (illustrator)

Why should I read it?

2 authors picked The Terrible Two as one of their favorite books, and they share why you should read it. This book is for kids age 9, 10, 11, and 12.

What is this book about?

Miles Murphy is not happy to be moving to Yawnee Valley, a sleepy town that's famous for one thing and one thing only: cows. In his old school, everyone knew him as the town's best prankster, but Miles quickly discovers that Yawnee Valley already has a prankster, and a great one. If Miles is going to take the title from this mystery kid, he is going to have to raise his game.

It's prankster against prankster in an epic war of trickery, until the two finally decide to join forces and pull off the biggest prank ever seen: a prank…


Book cover of Sam & Dave Dig a Hole

DK Ryland Author Of Have You Seen My Acorn?

From my list on where the reader knows more than the character.

Why am I passionate about this?

I am a picture book author/illustrator who writes humorous stories. One of my favorite techniques for instilling humor in my writing is for the illustrations to show the reader more than the characters’ know. It’s so much fun for kids to realize and be in on the joke before the characters in the book. I love a storytime where the kids get engaged and start pointing out what’s really happening and start talking to the characters to try to change their actions. I also love a good twist ending that makes the reader say, “How did I not see that coming?!” and these are the perfect kind of books for it. 

DK's book list on where the reader knows more than the character

DK Ryland Why did DK love this book?

Sam and Dave are digging for something spectacular and get so close to treasure that they keep deciding to change directions right when they are about to find it. I love this because, as a reader, you can see the treasure and how close Sam and Dave get.

The ending on this one is so fascinating because it’s open-ended, and that’s especially rare for a picture book. It's also a great conversation starter. 

By Mac Barnett, Jon Klassen (illustrator),

Why should I read it?

4 authors picked Sam & Dave Dig a Hole as one of their favorite books, and they share why you should read it. This book is for kids age 4, 5, 6, and 7.

What is this book about?

With perfect pacing, the multiple award-winning, best-selling team of Mac Barnett and Jon Klassen dig down for a deadpan tale full of visual humour.

From the award-winning team behind Extra Yarn, and illustrated by Jon Klassen, the Kate Greenaway-winning creator of This Is Not My Hat and I Want My Hat Back, comes a perfectly paced, deadpan tale full of visual humour. Sam and Dave are on a mission. A mission to find something spectacular. So they dig a hole. And they keep digging. And they find ... nothing. Yet the day turns out to be pretty spectacular after all.…


Book cover of The Stinky Cheese Man: And Other Fairly Stupid Tales

Chris Harris Author Of My Head Has a Bellyache: And More Nonsense for Mischievous Kids and Immature Grown-Ups

From my list on kids and grown-ups will laugh, gasp, and grin at.

Why am I passionate about this?

Reading with your kid can be a delight, but it’s tough to find a book that both grown-up and child think is hysterical. I mean, I tried reading Catch-22 to my three-year-old, but for some reason the incisive social commentary just didn’t resonate with her. My kids and I both let out genuine chuckles and guffaws while reading all of these books—an experience that I treasured. These books are all giggly, snickery proof that you don’t have to dumb things down to appeal to a wide age range—a goal that I aim for myself in the children’s books and TV shows that I write. 

Chris' book list on kids and grown-ups will laugh, gasp, and grin at

Chris Harris Why did Chris love this book?

This is the book that made my kids’ heads explode (not literally—this book is perfectly safe (as far as I know)) as it helped them discover the idea of parody: taking something familiar and twisting it in a funny, unexpected way.

We rolled and lol’ed together as we read Jon’s wild, hysterical takes on old fairy tales. The non-twist twist ending to his take on the ugly duckling story is still a running joke in our family. Jon’s The True Story of the 3 Little Pigs and The Real Dada Mother Goose are also great for the same reason.

By Jon Scieszka, Lane Smith (illustrator),

Why should I read it?

2 authors picked The Stinky Cheese Man as one of their favorite books, and they share why you should read it.

What is this book about?

The entire book, with its unconventional page arrangement and eclectic, frenetic mix of text and pictures, is a spoof on the art of book design and the art of the fairy tale. The individual tales, such as The Really Ugly Duckling and Little Red Running Shorts, can be extracted for telling aloud, with great success. Another masterpiece from the team that created The True Story of the Three Little Pigs!
-Horn Book


Book cover of I Can Only Draw Worms

Kyle Scheele Author Of A Pizza with Everything on It

From my list on for goofy kids.

Why am I passionate about this?

I’ve always been a goofball. When I was a kid, I was constantly getting in trouble for making my friends laugh in the back of the room. But then I would get out of trouble by making the teacher or the principal laugh. Humor and absurdity have always had a special place in my heart, and I love books like these that encourage us to not take ourselves quite so seriously!

Kyle's book list on for goofy kids

Kyle Scheele Why did Kyle love this book?

This book is such a fun example of taking something that could be seen as a limitation (for instance, the fact that you can only draw worms) and turning it into something more. The book is narrated by the author/illustrator, who explains that he can only draw worms. 

He then introduces a cast of worms and tells us about their various adventures. But whenever he describes something non-worm-like (Worm Six is riding on a flying unicorn!) he quickly reminds us that he can’t draw those things, because he can only draw worms. Never fails to get my kids laughing!

By Will Mabbitt,

Why should I read it?

1 author picked I Can Only Draw Worms as one of their favorite books, and they share why you should read it. This book is for kids age 3, 4, and 5.

What is this book about?

A hilarious picture book in bright, neon colors that is perfect for fans of The Book With No Pictures and The Day the Crayons Quit.

This is part counting book, part introduction to worms, but all superbly silly. The fact that the author/illustrator can only draw worms will not take anything away from the laugh-out-loud adventure readers will have as they turn the pages of this slightly subversive picture book.


Book cover of Frindle

Kyle Scheele Author Of A Pizza with Everything on It

From my list on for goofy kids.

Why am I passionate about this?

I’ve always been a goofball. When I was a kid, I was constantly getting in trouble for making my friends laugh in the back of the room. But then I would get out of trouble by making the teacher or the principal laugh. Humor and absurdity have always had a special place in my heart, and I love books like these that encourage us to not take ourselves quite so seriously!

Kyle's book list on for goofy kids

Kyle Scheele Why did Kyle love this book?

I was just recently introduced to this book by my friend Erica, and I love it so much! It’s a story that feels ridiculous and realistic at the same time. It starts out with a boy who is trying to distract his teacher long enough to avoid getting homework, but the plan backfires. Before we know it he’s gotten half the school in detention, started a nationwide trend, and gotten himself into the record books. It’s an ode to the power of silly ideas, and I can’t recommend it enough. 

By Andrew Clements,

Why should I read it?

1 author picked Frindle as one of their favorite books, and they share why you should read it. This book is for kids age 8, 9, 10, and 11.

What is this book about?

From bestselling and award-winning author Andrew Clements, a quirky, imaginative tale about creative thought and the power of words that will have readers inventing their own words.

Is Nick Allen a troublemaker? He really just likes to liven things up at school -- and he's always had plenty of great ideas. When Nick learns some interesting information about how words are created, suddenly he's got the inspiration for his best plan ever...the frindle. Who says a pen has to be called a pen? Why not call it a frindle? Things begin innocently enough as Nick gets his friends to use…


Book cover of Poison for Breakfast

Jocelyn Cole and Sharon Nagel Author Of Shady Hollow

From my list on off-kilter mysteries for off-kilter readers.

Why are we passionate about this?

We almost said “quirky” instead of off-kilter in this title. But quirky is becoming synonymous with cozy, which is weird because it doesn’t mean the same thing at all. So, off-kilter it is. Done well, playing with expectations makes for an especially engaging read. We’ve attempted that trick in our own Shady Hollow Mysteries, which uses the form of a traditional murder mystery, but in a world of anthropomorphic animals. So naturally we love when other authors play with the form. These five books all fit the description of “off-kilter,” and we hope you can find fun and joy in reading them.  

Jocelyn's book list on off-kilter mysteries for off-kilter readers

Jocelyn Cole and Sharon Nagel Why did Jocelyn love this book?

Lemony Snicket is no stranger to unfortunate events, but this standalone book contains perhaps the worst of all: the news that he, the author, has consumed poison while eating the first meal of the day. Of course, this being a Snicket story, there’s more going on. This book is a bit mystery, and a bit philosophy (or is it the other way around?). More importantly, it is also a meditation on the wonderfulness of books and reading, a part of life that remains important even if one is quite sure one has been poisoned and now has an indeterminate amount of time to discover the truth of what happened.

By Lemony Snicket,

Why should I read it?

6 authors picked Poison for Breakfast as one of their favorite books, and they share why you should read it.

What is this book about?

In the years since this publishing house was founded, we have worked with an array of wondrous authors who have brought illuminating clarity to our bewildering world. Now, instead, we bring you Lemony Snicket.

Over the course of his long and suspicious career, Mr. Snicket has investigated many things, including villainy, treachery, conspiracy, ennui, and various suspicious fires. In this book, he is investigating his own death.

Poison for Breakfast is a different sort of book than others we have published, and from others you may have read. It is different from other books Mr. Snicket has written. It could…


Book cover of Flora & Ulysses: The Illuminated Adventures

S.M. Stevens Author Of Shannon's Odyssey

From my list on adventure with talking animals and a dash of magic.

Why am I passionate about this?

As a girl, I would roll around on the floor with my Labrador retriever, beg my parents for horseback-riding lessons, and dream of being a vet. A proficiency in language and lack of science skills led me to writing instead, but my intense love of animals never waned. I adore adventure stories featuring animal characters and human ones, and some form of communication between them. That’s why I wrote Shannon’s Odyssey which, like many Middle Grade novels, also explores family secrets and the all-important act of forgiveness. It’s not fantasy but contains mystical elements rooted in reality, because who doesn’t want to believe magic exists in our everyday lives?

S.M.'s book list on adventure with talking animals and a dash of magic

S.M. Stevens Why did S.M. love this book?

Clever, comic-book reading, word-loving Flora is more cynical than ever since her parents’ separation. She’s sure her mother loves a shepherdess lamp more than her own daughter. When Flora saves a squirrel sucked up by a neighbor’s vacuum and he returns with super strength and the ability to understand language and write poetry, she finds a kindred spirit. I love this book for its colorful (human and squirrel) characters and subtle exploration of family dynamics. And I love that Flora’s journey, which is emotional rather than physical, isn’t wrapped up with a tidy bow at the end.

By Kate DiCamillo, K.G. Campbell (illustrator),

Why should I read it?

5 authors picked Flora & Ulysses as one of their favorite books, and they share why you should read it. This book is for kids age 8, 9, 10, and 11.

What is this book about?

Holy unanticipated occurrences! A cynic meets an unlikely superhero in a genre-breaking new novel by a master storyteller.

It begins, as the best superhero stories do, with a tragic accident that has unexpected consequences. The squirrel never saw it coming - the vacuum cleaner, that is. As for self-described cynic Flora Belle Buckman, she has read every issue of the comic book Terrible Things Can Happen to You! so she is just the right person to step in and save him. What neither can predict is that Ulysses (the squirrel) has been born anew, with powers of strength, flight and…


Book cover of The Adventures of Captain Underpants

Stephanie Calmenson Author Of Our Principal Is a Frog!

From my list on funny easy-to-read chapter books in a series.

Why am I passionate about this?

I landed my dream job teaching kindergarten in a Brooklyn public school, but it soon ended thanks to citywide budget cuts.  Wanting to continue connecting with children, I made my way into children's book publishing first as an editor, later as a writer.  I've now written over 100 books including Dinner at the Panda Palace (PBS StoryTime book); May I Pet Your Dog? (Horn Book Fanfare); Dozens of Dachshunds (Scholastic Book Club selection); the Our Principal series (S&S Quix books); and The Adventures of Allie and Amy series, written with Magic School Bus author Joanna Cole. I found my new dream job teaching, entertaining, and encouraging children through books.

Stephanie's book list on funny easy-to-read chapter books in a series

Stephanie Calmenson Why did Stephanie love this book?

No list of funny, easy chapter books would be complete without Captain Underpants! This first book in the series introduces us to best buddy mischief makers George and Harold who hypnotize their principal, turning him into Captain Underpants. George and Harold are good kids. Really. I mean it. They just happen to have a mile-long "silly streak".  While not every adult approves of these books because the kids are cheeky, this is humor that gets kids reading. It's an honorable goal with exemplary execution. (Note: Author-illustrator Dav Pilkey was diagnosed as a kid with ADHD and dyslexia. At school, he was sent to sit out in the hallway daily. His success story, shared at the end of the book, is inspiring.)   

By Dav Pilkey,

Why should I read it?

3 authors picked The Adventures of Captain Underpants as one of their favorite books, and they share why you should read it. This book is for kids age 7, 8, and 9.

What is this book about?

Laugh out loud with the first Captain Underpants,
the #1 New York Times bestselling series
from Dav Pilkey, the creator of Dog Man!


This edition is a full-colour graphic novel



Fourth graders George Beard and Harold Hutchins are a couple of
class clowns.

The only thing they enjoy more than playing practical jokes is
creating their own comic books.

And together they've created the greatest superhero in the history
of their elementary school: Captain Underpants!

His true identity is SO secret, even HE doesn't know who he is!



The critics are CRAZY about UNDERPANTS!

"Irresistible." - Entertainment Weekly

"Call Pilkey...…


Book cover of Meet the Bigfeet

Travis Nichols Author Of A Witch's Last Resort

From my list on friendly freaks, monsters, and cryptids.

Why am I passionate about this?

I’m a lifelong monster fiend. I love horror and sci-fi, and I especially love stories that really dig into characters and how they smash into each other. My favorite scary books (and movies, etc.) are funny, and my favorite funny books are kinda scary. It can be super healing and empowering to read books about terrible things that are handled with a heaping scoop of empathy and humor and absurdity.

Travis' book list on friendly freaks, monsters, and cryptids

Travis Nichols Why did Travis love this book?

Cryptids? Gnomes? Maps and charts? I’m in heaven.

I don’t know Kevin, but he feels like a kindred spirit who grew up on the same set of references. The Yeti Files books are hilarious and cool with a huge cast of cryptids (check the endpapers for a roll call). Marlon the skunk ape is my favorite.

I love the way the story of Blizz attending his family reunion and thwarting George the cryptozoologist is told: illustrated spreads, whooshing panels, Indiana Jones-esque dotted line traveling interludes, etc.

The rhythm and pace surf you from page to page. Reluctant readers don’t stand a chance.

By Kevin Sherry,

Why should I read it?

2 authors picked Meet the Bigfeet as one of their favorite books, and they share why you should read it.

What is this book about?

Yetis, Bigfeet and goblins abound in this hilarious new illustrated
series from a bestselling author/illustrator!

Blizz Richards is a great guy, a caring boss and a loyal friend.
Oh, yeah ... he's also a yeti! He's made it his life's mission to
study cryptids like him; hidden animals who have taken a powerful
oath to never be seen by the outside world.

So when a photo of Cousin Brian becomes a media sensation, Brian
can't handle the guilt and disappears. But it's time for the annual
Bigfoot family reunion, and it won't be the same without him.
Luckily, Blizz and…


Book cover of Matilda
Book cover of The Terrible Two
Book cover of Sam & Dave Dig a Hole

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