The best middle-grade books that will make you laugh

Allan Woodrow Author Of The Curse of the Werepenguin
By Allan Woodrow

The Books I Picked & Why

Sideways Stories from Wayside School

By Louis Sachar, Adam McCauley

Book cover of Sideways Stories from Wayside School

Why this book?

A series of standalone, but connected stories centered around the strangest elementary school you’re likely to ever see. Louis Sachar is one of my all-time favorite kid writers and I recommend all of work (his Newberry Winning “Holes” is one of my top five favorite books of all time). Wayside School was accidentally built sideways so it stands 30 stories high. Lots of strange things happen at the school, especially on the 13th floor where Mrs. Gorf may be the meanest teacher of all time. There are three more books in this series, and they are all hysterical, but if you’re going to start somewhere, start with the first one.

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Flora & Ulysses: The Illuminated Adventures

By Kate DiCamillo, K.G. Campbell

Book cover of Flora & Ulysses: The Illuminated Adventures

Why this book?

A Newberry Medal winner from the peerless Kate DiCamillo (quick, read all her books!), with comic panels from K.G. Campbell. Flora is a 10-year-old girl and Ulysses is a squirrel with superpowers, who Flora rescues from a vacuum cleaner. You’re already giggling, aren’t you? We follow the pair, and a bunch of other wacky characters, on a series of laugh-out-loud adventures that will keep you turning the page. I bet you’ll read the entire book in one sitting, like I did. 

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By Roald Dahl, Quentin Blake

Book cover of Matilda

Why this book?

Oh, c’mon. Do you have to ask? Roald Dahl was a genius, and it was hard to pick just one of his books. Honestly, I waffled between this book and three others. But what sets Matilda apart is its heart—and when a book has heart it makes the funny parts funnier, and those grow inside you a little bit (it also makes the suspense parts feel more suspenseful and the sadder parts feel sadder). Matilda is a sweet girl who doesn’t get along with the school’s kid-hating headmistress, Miss Trunchbull. In fact, things look bleak for Matilda until she discovers some exceptional superpowers hidden inside her. 

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The Terrible Two

By Jory John, Mac Barnett

Book cover of The Terrible Two

Why 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. 

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The Adventures of Captain Underpants (Captain Underpants #1)

By Dav Pilkey

Book cover of The Adventures of Captain Underpants (Captain Underpants #1)

Why this book?

Oh, really, do you have to ask “why this book?” I mean, how can I make a list of funny middle school books and not include Captain Underpants? Frankly, this list could just consist of Dav Pilkey books and I’d be fine with it, from Dog Man to Super Diaper Baby. The whimsical yet simplistic drawings make his absurd stories that much funnier. And really, any book featuring drawings of an adult in diapers is going to be funny. 

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