10 Hilarious Children's Books

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Creating age appropriate material without condescending to the reader is no easy task for children’s book authors. When it works, though, great children’s literature appeals as much to adults as to kids. Though thrilling books like Watership Down and Mrs. Frisbee and the Rats of NIMH transition well into adulthood, it’s harder to find books that are funny to both children and their parents. These ten books, however, deserve special applause for hitting that sweet spot.

10. Sideways Stories from Wayside School by Louis Sachar

Louis Sachar has written many acclaimed books for children, and while Holes is probably his strongest book, Sideways Stories from Wayside School was chosen for its inventive humor. Structurally interesting — the book consists of thirty short chapters, each focusing on a different student or teacher — Wayside School paints a picture of a school where anything can and does happen. Over the course of the three books in the series, the students meet a variety of strange teachers, from the terrifying Mrs. Gorf (who turns them all into apples) to the bitter Ms. Nogard (whose third ear on her head allows her to read people’s minds). The kids take all of the strange events in the book in stride, and they appear bewildered by tales of other schools where children do “normal” activities.

9. Don’t Let the Pigeon Drive the Bus by Mo Willems

Don’t Let the Pigeon Drive the Bus works wonders through its expressive minimalism. The tale of a frustrated pigeon who just really wants to drive a bus, the book milks humor from desperation. The pigeon whines, wheedles, and begs you, the reader, to break the command of the absent bus driver and let him hop into the driver’s seat — even to steer for just a minute. His frustrations eventually reach the breaking point, and he explodes in hilarious rage. Though ultimately unsuccessful, the pigeon remains undaunted and ultimately turns his attention to an even bigger prize: an eighteen wheeler.

8. The Sword in the Stone by T.H. White

Arthur grows up as the ward of a gentleman named Sir Ector, a well-meaning but slightly stupid knight. His prospects look bleak until he meets Merlyn, the time-traveling wizard who has come to train him up to be king of England. For Merlyn, this means transforming Arthur into a series of animals so the boy may learn lessons from the natural world. These transformations offer plenty of ripe, comedic moments, as Arthur finds himself adjusting to life as a fish out of water — sometimes literally. The real stars of the book, however, are Merlyn and his pet owl Archimedes. Merlyn has been portrayed in many different lights over the years, but White’s wizard stands out for the larger than life comic presence he brings to the tale. A man who lives his life backwards, Merlyn constantly spouts anachronisms referencing 20th Century events with a knowing wink to the reader. Merlyn is also gloriously absent-minded and relies on Archimedes to keep him in line.

7. The House at Pooh Corner by A.A. Milne

Forget the million and a half Disney adaptations; even the good ones fail to capture the droll magic of Milne’s original Winnie-the-Pooh stories. Through the imagination of Christopher Robin, a stable of quirky characters, none more so than that “silly old bear,” come to life. Gentle in spirit and simple in plot, the Pooh stories revel in the innocence of childhood and the charm of imagination.

What may surprise those with only cursory knowledge of these tales is how funny they are. The characters are sharply drawn, each with their own peculiarities. Owl comes across as a know-it-all with the wrong answers, and Eeyore is even more deliciously downbeat than he appears in the cartoons. Pooh himself provides much of the comedy, as malapropisms flow from his mouth like honey in one of his pots. He may end up in many a scrape thanks to his less than stellar reasoning faculties, but this only adds to his comic likeability.

6. Alice’s Adventures in Wonderland & Through the Looking-Glass by Lewis Carroll

Wonderland has become synonymous with the weird, wild workings of fantasy worlds. When Alice falls down that famous rabbit hole, she discovers a world of wonders and oddities. She meets characters like Tweedledee and Tweedledum, who always contradict each other, and the infamous Mad Hatter, who will befuddle the reader with bizarre riddles. Carroll also peppers his stories with poetry, much of it nonsensical. “Jabberwocky” of course stands out, but others like “You Are Old, Father William” and “The Lobster Quadrille” are just as hilarious and weird. Whether through poetry or prose, Carroll’s writing conveys the absurd humor of life.

5. Where the Sidewalk Ends by Shel Silverstein

If you want a child to love poetry, introduce them to Shel Silverstein at an early age. The kid-friendly version of Ogden Nash, Silverstein writes with a mixture of humor and wonder. Silverstein has a gift for understanding a child’s perspective, and much of his humor stems from people focusing on details while missing the big picture. Poems like “Homemade Boat,” where the narrator insists his homemade boat is great even though he forgot to build a bottom, capture the disconnect between intentions and results in the life of a child.

4. The Stinky Cheese Man and Other Fairly Stupid Tales by Jon Scieszka

Jon Scieszka, like Louis Sachar, is a fixture of the contemporary children’s literature world. By far his funniest book, The Stinky Cheese Man is a collection of warped retellings of traditional tales. These include a new versions of “The Princess and the Pea,” where the prince cheats by putting a bowling ball under the mattress of the girl he likes, and “The Other Frog Prince,” where the amphibian gets the princess to kiss him only to reveal he’s actually just a frog after all. What makes the book really special, though, is its postmodern sensibilities. Children will only recognize the spirit of play and absurdity present, but adults will appreciate the formal daring of this twisted book.

3. The Adventures of Asterix by Rene Goscinny

Much of the humor of the Asterix books revolves around wordplay, especially the use of names. Asterix and his best friend Obelix are puns themselves (asterisk and obelisk), but the real fun comes from the other villagers. Obelix’s dog is named Dogmatix (he’s a devout dog, no doubt), the chieftain’s name is Vitalstatistix, and — best of all — the druid who brews magical concoctions is called Getafix. But Asterix features more than just puns aplenty; humor also arises in large part thanks to the characterization in the series. Asterix is the traditional straight man with a level head, but everyone around him ranges from eccentric to certifiable. From the dumb Romans who line up to get punched by Obelix to the world’s sorriest band of pirates, each character has off-kilter part to play in Goscinny’s amusing world.

2. Revolting Rhymes by Roald Dahl

It would be easy to create a separate list just ranking Roald Dahl’s books with regards to their hilarity. Dahl consistently creates twisted, savagely funny worlds for children to explore. Choosing a single representation of his work is a challenge, but the book that stands apart is Revolting Rhymes. Though not as well-known as some of his chapter books, the collection of fairy tale poems nevertheless reveals Dahl at his vicious, witty best.

At the end of each fairy tale (there are five), comes a twist which undermines the traditional moral of the story. Snow White, for example, finds herself teamed up with seven jockeys who obsessively bet on races. So she decides to steal the Queen’s magic mirror, proving that “Gambling is not a sin/provided that you always win.” The humor comes largely from the ways in which Dahl undermines these famous tales, but his ear for verse is equally amusing.

1. The Phantom Tollbooth by Norton Juster

This is it, folks, the bar none funniest children’s book ever written. A loopy, goofy tale of a boy who discovers the power of imagination,The Phantom Tollbooth has delighted children and adults alike for over 50 years.

Once he drives his toy car through the titular tollbooth, Milo discovers a world where rules disappear, clichés are literal, and language is unmoored in hilarious ways. As Milo travels to rescue the princesses Rhyme and Reason, he encounters a variety of memorable characters and bizarre destinations. It’s clear Juster wanted to show children the joys of language, and in doing so, he created an unparalleled world of play and humor.

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