Rodrick Rules
Rodrick Rules - 2008
If you want to skip straight to the book most people say is the funniest. The sibling rivalry with Rodrick is peak Wimpy Kid.
Beginner guide
The best Jeff Kinney book to start with
A big catalog is intimidating. Here's exactly where to begin - and what to skip first. - Updated June 2026
Why start here
Greg Heffley is one of the most recognizable characters in kids' fiction. His unreliable narration and terrible decision-making are the engine of every book.
The mix of hand-drawn illustrations and journal-style text makes these books accessible to reluctant readers who resist traditional chapter books.
Kinney's humor is sharp and observational. He captures the absurdity of middle school without condescending to his audience.
The first book sets up Greg's world, his family dynamics, and his friendship with Rowley, which all carry through 18 more books.
Other good entry points
Depending on what you're in the mood for.
Rowley Jefferson's Awesome Friendly Adventure
Rowley Jefferson's Awesome Friendly Adventure - 2019
If you want a softer entry point. Rowley's spin-off is gentler and less cynical than Greg's diaries.
Dog Man (Dav Pilkey)
Dog Man (Dav Pilkey) - 2016
If your kid wants more illustrations and less text. Dog Man is a graphic novel series for the same age group.
What not to start with (yet)
Great books - just not first.
The Wimpy Kid Movie Diary - 2010
A behind-the-scenes book about the film adaptations, not a story. Kids expecting a new Wimpy Kid adventure will be disappointed.
The Wimpy Kid Do-It-Yourself Book - 2008
An activity book, not a novel. Fun for fans but not where to start.
Ready to start with Diary of a Wimpy Kid?
Kindle, paperback, or listen free on Audible.
Frequently asked questions
Not strictly. Each book covers a self-contained period in Greg's life. But character introductions and running jokes work best from the beginning, so starting with book one is recommended.
Not really. Greg is selfish, dishonest, and never learns from his mistakes. That is the joke. Kinney has said the humor comes from watching Greg make the wrong choice every time. Kids find this hilarious.
Ages 8 to 12 is the sweet spot. The humor, illustrations, and short chapters make these especially popular with kids who say they do not like reading.
Contains affiliate linksUpdated June 2026