Mischief, marmalade and minor disasters: 5 funny reads

Every now and then, when you’re young, you stumble across a book that makes you laugh so hard you have to put it down to breathe. Not just a book with the odd chuckle – but the kind of read that you remember for the rest of your life. 

These are five of my all-time favourite books – they have never failed to cheer me up, however many times I reread them. Some involve schoolboy schemes. One involves custard. Another involves a bear floating away with a blue balloon and a very serious plan. 

The first book I remember making me laugh was Winnie-the-Pooh by A.A. Milne, which is about a bear who loves honey and lives in Hundred Acre Wood with his friends Piglet, Eeyore, Tigger, Rabbit, Owl, Kanga and Roo, not forgetting Christopher Robin – a young boy who is like a big brother: brave, thoughtful and fair. (Maybe not like everyone’s big brother.) 

What were the stories about? One story is about when Eeyore loses his tail and they set off to find it, finally discovering Owl is using it as a bell pull on his door and Christopher Robin reattaches it with a drawing pin. 

My wife and I used to read Winnie-the-Pooh to our two sons when they were young and they both used to roll around with laughter. One of the boys even fell off the bed laughing. Always a good sign that something is funny. 

Pooh may be a bear of Very Little Brain, but don’t be fooled. Milne’s prose is packed with quiet absurdity, dry asides and philosophical whimsy. Piglet’s constant panic, Eeyore’s sarcastic gloom, and Owl’s muddled pomp are pitch-perfect comic turns – and Pooh’s broken logic (“I wasn’t going to eat it, I was just going to taste it”) never gets old. 

It’s strange that two of these books involve bears. One loves honey; the other loves marmalade. It’s amazing they never met. 

Paddington arrives in England with his suitcase, a hat, and the firm belief that he’s being very helpful. The results are… spectacular. From flooding bathrooms to mistaking barbershop etiquette for medieval torture, Paddington handles every situation with polite determination and absolutely no awareness that he’s causing total mayhem. 

Schoolboy enthusiasm meets absolute disaster. 

The first of the Jennings books is a wonderful boarding school farce. Jennings means well, but his eagerness leads him into ever-expanding circles of confusion. Luckily, he has his sidekick Darbyshire… who is no help at all. 

Expect fossilised fish, Latin puns, secret plans, and things that go crash in the dormitory. 

The crown jewel of British comic prose. My mum loved P.G. Wodehouse. She thought the books hilarious, and she was right. 

Bertie Wooster is a well-meaning idiot; Jeeves is the all-knowing valet trying to stop his employer from causing international incidents at country house weekends. 

Wodehouse’s language is like champagne – bubbly, surprising, and just a little bit dangerous. This is probably the funniest of the Jeeves books, with hopeless romances, prize-winning newts, and Bertie accidentally lighting a roomful of relatives on fire. 

This book is wickedly funny, with wit, clever wordplay, and a narrator who treats misery as comedy. Children feel like insiders to the joke, laughing at calamity while secretly learning new words. 

These books work because they’re full of affectionate chaos. They don’t mock their characters – they celebrate their flaws, their mistakes, and their well-meant disasters. There’s no cruelty, just the comforting reminder that even when everything goes wrong, you might end up somewhere wonderful. Possibly covered in jam. 

Did I miss your favourite comic classic? Are you team Bertie or team Paddington? Drop me a line with your go-to laugh-out-loud reads. I’m always on the lookout for more literary mayhem. 

Sin Bin Island by Doug Naylor is out now.