Diary of a Wimpy Kid is the ultimate Trojan horse of children’s literature: it looks like a comic book, reads like a secret journal, and somehow convinces kids who "don't like reading" to finish 200+ pages in a single sitting. Greg Heffley isn't a hero, he isn't particularly kind, and he’s definitely not a role model—but for a middle-schooler navigating the social minefield of the cafeteria, he is the most relatable person on the planet.
The Diary of a Wimpy Kid 23-book collection is a massive win for building reading stamina in reluctant readers, using a mix of cynical humor and doodle-heavy pages to demystify middle school. While Greg Heffley is a famously selfish protagonist, his flaws make him a perfect mirror for real-world social dynamics. For more high-interest series, check out our best books for kids list.
The genius of Jeff Kinney’s series isn't the prose; it’s the friction-free design. By using a handwritten font on lined "notebook" paper and peppering every page with stick-figure illustrations, Kinney removes the intimidation factor of a dense novel.
For a kid who feels overwhelmed by a wall of text, this 23-book box set is the ultimate "I can do this" moment. They aren't just reading a story; they’re binge-watching a diary. The paperback format is also key—it’s light, portable, and feels less like a school assignment and more like a comic book.
The most common parent critique of Diary of a Wimpy Kid is that Greg is kind of a jerk. He’s lazy, he lies to his parents, and he often treats his best friend, Rowley, like an accessory.
Here’s the Screenwise take: Greg’s jerkiness is the point.
Most middle-grade books feature kids who are preternaturally brave or morally upright. Greg is neither. He is a self-absorbed, status-obsessed tween—which is exactly what middle school feels like from the inside. Because Greg is an "unreliable narrator," kids often realize he’s being a brat before Greg does. It’s a low-stakes way for them to practice social-emotional intelligence: they see Greg make a terrible choice, watch it blow up in his face, and learn the lesson without having to live through the embarrassment themselves.
Buying the complete collection (Books 1-23) is a commitment, but it solves the "what do I read next?" problem for months. The series has a formula, and while critics might call it repetitive, kids call it "comfortable." Knowing exactly what to expect from the next installment—the same humor, the same family dynamics with Rodrick and Manny, the same "Zoo-Wee Mama!" energy—builds the kind of reading confidence that eventually leads them to more complex work.
If they blast through the first few books, they’ve already built a habit. By the time they hit book 23, they’ve read hundreds of thousands of words without even noticing.
If your kid has already memorized the Diary of a Wimpy Kid lore, they’re likely looking for that same mix of snark and sketches. Here are three deeper cuts that hit the same vibe:
If Greg Heffley is a cynical realist, Timmy Failure is a delusional optimist. He’s a "detective" with a polar bear partner and a total lack of self-awareness. It’s arguably funnier than Wimpy Kid and leans harder into the "unreliable narrator" trope.
This is for the kid who loves the "prank" aspect of the Heffley brothers. It’s about two rival pranksters in a town obsessed with cows. It’s smart, fast-paced, and has that same visual-heavy layout that keeps reluctant readers engaged.
For the younger end of the Wimpy Kid audience, this series is pure chaos. It’s a graphic-novel-hybrid about a squad of pigeons who solve mysteries. It’s absurd, high-energy, and perfect for kids who love the "doodle" aesthetic.
The biggest friction point isn't the language (which is very mild) or the "violence" (which is purely slapstick). It’s the cynicism. Greg lives in a world where parents are often clueless, teachers are obstacles, and being "cool" is the only currency that matters.
Pro-tip: Don't fight the cynicism; use it. Ask your kid, "Do you think Greg was actually a good friend to Rowley in this chapter?" or "Why did Greg's plan fail?" It turns a "brain-candy" book into a masterclass in reading between the lines.
You don't need to do a deep dive into the themes of suburban ennui. Just lean into the humor.
- "Which of Greg’s brothers is actually the worst: Rodrick or Manny?"
- "What’s the most embarrassing thing that’s happened in these books so far?"
- "If you were Rowley, would you still be friends with Greg?"
Q: Is Diary of a Wimpy Kid appropriate for a 7-year-old? Yes, it’s physically safe and the content is mild, but the humor is really designed for the 8-12 age range. A 7-year-old might enjoy the pictures, but the social satire and "middle school" angst might go over their head until they're a bit older.
Q: Are the Diary of a Wimpy Kid movies better than the books? The Diary of a Wimpy Kid movies (especially the original live-action trilogy) are actually quite good, but they make Greg a bit more "likable" than he is in the books. The books are the purer version of the character, but the movies are a great family-night follow-up after they finish the first few installments.
Q: Does the series get repetitive after 23 books? To an adult? Absolutely. To a kid? Not really. Jeff Kinney has a "sitcom" approach where the status quo is usually restored at the end of every book, which is exactly why kids find it so easy to pick up any book in the series and start reading.
Q: Is Greg Heffley a bad influence? Only if you expect him to be a role model. If you treat him like a "what not to do" guide, he’s actually a great teaching tool. Most kids recognize that Greg is his own worst enemy.
The Diary of a Wimpy Kid box set is a massive investment in your kid's reading life. It’s not Shakespeare, but it’s the bridge that gets them from "I have to read" to "I want to read." Grab the set, ignore the stick-figure snark, and watch them actually finish a series for once.
- Looking for more series they can't put down? See our best books for kids list.
- Navigating the transition to middle school? Check out our digital guide for middle school.
- If they’re aging out of Greg Heffley, try our digital guide for high school for what comes next.