The Next Ten Diary of a Wimpy Kid Books, Ranked From Worst To Best

Hey everyone, and I’m back with an interesting new post relating to Diary of a Wimpy Kid. So, you might remember when I said that in August 2018, my post of the first ten Diary of a Wimpy Kid books from worst to best dethroned my initial post about the Diary of a Wimpy Fall as my most viewed post on the blog. No other post has dethroned it since, though my other book ranking posts have come close, suggesting that they are the most popular type of post on the blog. Obviously, I couldn’t be more grateful for all of the traffic I’ve received around the world, from not just that post, but my other posts as well. None of this is lost on me, which is why I had an idea for the longest time now.

As you may know by now, the 20th Diary of a Wimpy Kid book, Partypooper, has been released. And I’ve been way behind on the series, partly due to finally growing out of the books in a sense, but also because of my commitment to personal projects. So, I figured that to commemorate the momentous occasion of the series reaching the 20-book milestone, and in response to the apparent demand, I’ve decided to make a second part to my post ranking the first ten books from worst to best by ranking the next ten books in the series from worst to best.

Now, I know what you might be thinking. Why? It’s no secret that the series has declined in quality since Old School, feeling more like a spin-off of the first ten books instead of an actual continuation. Because of that, ranking the next ten books wouldn’t be as interesting compared to ranking the first ten, right? But personally, I’m interested in seeing how all the mediocrity stacks up with one another. The books might not be as good as they used to be, but is each succeeding book really worse than the previous? Are there diamonds in the rough that is modern Diary of a Wimpy Kid, even if those diamonds are a bit rough themselves?

Not that I’m endorsing the mediocrity either, of course. I know that I declared a Diary of a Wimpy Revival with the launch of the animated film series and Poptropica’s explanation for Jeff Kinney’s absence back in February 2021. But nowadays, I wouldn’t call it a revival or a fall, just…a really odd in-between. Depressingly, in October 2024, the company that made Poptropica shut down. Luckily, it was moved to Cool Math Games, and although the new owners claim to be committed to the game’s future development, they haven’t yet updated the game since they acquired it. In the Poptropica Help Blog’s post announcing the shutdown, I made a comment asking why Jeff Kinney couldn’t have just kept funding the game before all this happened. Hot Mess was still coming out later that month. I also stated that I’m not even asking Kinney to focus on Poptropica again, but he could probably pour a fraction of his earnings into the game, and it would barely affect his revenue.

Curiously, 2024 also marked the first year an animated Diary of a Wimpy Kid film was not released on Disney+ since Kinney started helping produce them in 2021. It made me wonder if it was a sign that Kinney might pivot back to Poptropica instead of helping produce a fourth movie. But as it turned out, an adaptation of The Last Straw had in fact been in development and had been stalled due to the 2023 Writers Guild of America and SAG-AFTRA strikes. The film has been confirmed for December, which is a positive development, of course, and it’s a film I’m nonetheless excited to watch. Kinney also announced plans to develop downtown Plainville (the location of his bookstore, An Unlikely Story) back in February 2024. That’s admittedly a way better use of his money than reinvesting it into Poptropica, but it also makes it even less likely he’d ever revisit the game.

As far as Poptropica is concerned, I’ve gotten some unexpected closure from a great commenter named Wimpy Fan a while back. They cited Kinney’s most recent comments on Poptropica in May 2024, in which they pointed out how Kinney speaks about Poptropica in the past, rather than in the present. Kinney’s phrasing makes them think Poptropica is more like a “legacy” to be preserved, rather than a game that will continue to receive updates. They go on to frame Kinney’s career in video game terms, noting that he finished the “main story” – fulfilling his dreams of becoming a cartoonist and author, taking part in the release of a successful movie trilogy, and founding and developing a fondly remembered children’s video game. Now, he has moved on to “side quests” that aren’t necessarily what he’ll be most remembered for, but are still worthy projects to him, such as contributing to his town, writing more books and producing the animated movies. 

Ultimately, Wimpy Fan is not convinced that Kinney has anything to prove with regards to Poptropica, but does admit that from a fan’s point of view, it would be great if he could come back to the game someday. Admittedly, I used to be a lot more adamant about Kinney returning to Poptropica, directly or indirectly. But now I’ll take it or leave it regarding his potential return. It is worth noting that Poptropica is among the few virtual worlds that are still active when so many others actually did shut down completely, so it’s a relief that Kinney at the very least believes in the game’s preservation. As long as the game still exists, there is hope for it. And all Poptropica really needs is money and passion. Maybe someday, a fan with enough money will be willing to breathe life back into the game. And I’ll support anything else Kinney does as long as it’s good. The 20th book is another fitting place to end the series if Kinney wanted to end it, though I doubt it. So, here’s to the next ten books being better than the last ten, and maybe even just as good as the first ten. And of course, I’d like to give a heads up to some spoilers in the books before I begin.

Anyway, on with the wimp-tastic countdown of greatness okay-ness!

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