Funny is the only category where a book’s job is obvious within a page, and the only one where a tween will tell you immediately if it has failed. These ten are the ones that reliably work — heavy on illustrated series, because that is where the laughs per page are highest, with two Roald Dahls at the end for readers who want the jokes in prose.
Diary of a Wimpy Kid by Jeff Kinney
The one that converted a generation. Greg Heffley is not a good person and the book knows it, which is most of the joke. The handwriting font and the cartoons mean a page turns in about ten seconds, and twenty books later the formula has not worn out. If a tween says they hate reading, this is still the first thing to try.
Dog Man by Dav Pilkey
A police dog and a policeman, surgically combined. Pilkey writes at exactly the frequency an eight-year-old finds funniest — puns, Flip-O-Ramas, deliberate misspellings — while quietly running a real story about whether anyone can change. The most borrowed books in most school libraries, and not by accident.
The Bad Guys by Aaron Blabey
A wolf, a shark, a snake and a piranha go straight. Mr. Wolf decides the gang should do good deeds instead, and the gang is terrible at it. Enormous type, cinematic panels, and roughly 140 pages that take twenty minutes. The highest laughs-per-page ratio on this list.
Big Nate: In a Class by Himself by Lincoln Peirce
A fortune cookie, taken far too seriously. Nate is told he will surpass all others today and spends the day trying to work out how. Peirce came from newspaper comics and it shows — the gags land on a beat, and the school detail is unusually accurate for a book this silly.
See Big Nate: In a Class by Himself →
The Terrible Two by Mac Barnett and Jory John
A prank war, escalating. Miles arrives at a new school planning to be its best prankster and discovers the position is taken. The pranks are genuinely clever rather than gross, which makes this the one on the list adults tend to enjoy reading aloud.
The Strange Case of Origami Yoda by Tom Angleberger
A finger puppet that gives good advice. Dwight is the weirdest kid in sixth grade, but the paper Yoda on his finger keeps being right, and the book is assembled as a case file of testimony from classmates arguing about whether it is real. Funny, and sneakily the most humane book here.
See The Strange Case of Origami Yoda →
The Adventures of Captain Underpants by Dav Pilkey
Two boys hypnotize their principal. Twenty-five years on, the premise still does the work: George and Harold turn Mr. Krupp into a superhero in underwear who cannot be turned back. Pilkey’s second entry on this list, which is fair — nobody else has done this twice.
See The Adventures of Captain Underpants →
My Weird School: Miss Daisy Is Crazy! by Dan Gutman
A teacher who cannot read, allegedly. Short, broad and relentlessly silly, aimed at the youngest end of this age range. Gutman repeats his jokes on purpose, which is exactly what a seven- or eight-year-old wants and exactly what makes the series so easy to finish.
See My Weird School: Miss Daisy Is Crazy! →
Matilda by Roald Dahl
A genius, and the worst headmistress in fiction. Dahl is funniest when he is being cruel to adults, and Miss Trunchbull is the high point of that entire career. The comedy is sharper than anything else on this list, and it is the one most likely to be reread at fifteen.
The BFG by Roald Dahl
A giant with his own vocabulary. Snozzcumbers, frobscottle and the whizzpopping that follows. The invented language is the joke, and reading it out loud is the only correct way to do it. Gentler than Matilda and a better fit at the younger end.
If nothing else has worked
Start with The Bad Guys. It is the shortest, the most illustrated and the fastest to finish, and finishing a book is the thing that changes a reluctant reader’s mind, not the book itself. Dog Man is the natural next step, and Diary of a Wimpy Kid after that, by which point the habit is usually doing its own work.
On the two-author problem
Dav Pilkey and Roald Dahl each appear twice above, which is not padding — between them they account for a large share of what tweens actually find funny in print. If both land, both have long backlists behind them, and that is generally a better next step than jumping to a new author.
Keep browsing
Every book above has a page in our catalog. Three of these series have full reading orders here: Dog Man, The Bad Guys and Diary of a Wimpy Kid. If the illustrations are the draw, see graphic novels for tweens, and if this is a conversion project, books for reluctant readers.