Twelfth Night by William Shakespeare

Shakespeare’s comedies are often good for some cross-dressing hijinks and mistaken identities (see also: Much Ado About Nothing, As You Like It), and Twelfth Night is no exception, thanks to identical twins Viola and Sebastian. But in addition to the usual farcical mix-ups, this play also features some actual pranks played by Toby Belch and his friends on Malvolio to humiliate him by convincing him to wear strange clothes and go around smiling everywhere..

Br’er Rabbit

A classic embodiment of the Jungian trickster figure, Br’er Rabbit tricks and manipulates his way out of sticky situations, famously using reverse psychology to get Br’er Fox to toss him into a briar patch—from which he easily escapes.

The Adventures of Tom Sawyer by Mark Twain

Tom Sawyer’s ability to trick his friends into doing the tedious chore of whitewashing a fence for him is a classic, and an inspiration to sluggards to this day.

The Twits by Roald Dahl

Dahl’s children’s books are filled with pranks and mischief—including Fantastic Mr. Fox and Matilda—but the horrible couple in The Twits put most childish pranksters to shame. The miserable husband and wife are just awful to each other, and it’s hilarious: she puts her glass eye in his beer and worms in his spaghetti; he gradually makes her cane longer so that she thinks she’s shrinking. And in the end, the neighborhood animals manage to glue all the Twits’ belongings to the ceiling in a final act of revenge against the foul couple.

The Hobbit by J.R.R. Tolkien

Trying to find his way out of goblin tunnels, Bilbo Baggins engages in a game of riddles with Gollum and tricks him into leading the way back to the surface.

Jane Eyre by Charlotte Brontë

While not a novel known primarily for wackiness, Jane Eyre does feature a prank in the form of Mr. Rochester dressing as a gypsy woman to tell the fortunes of his houseguests (and gauge their reactions to his predictions). Seemingly a minor comic interlude at first, it actually proves informative to Rochester and influences his actions and interactions with other characters for the rest of the book.

“The Cask of Amontillado” by Edgar Allan Poe

The main character of this grim tale, Montresor, is annoyed at his inaptly named friend Fortunato for an unspecified insult, so he decides to get his revenge. He chains up Fortunato in his wine cellar, and builds a wall to trap him inside, where he meets his death. Now THAT’S how you prank someone.