The First 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. Before you jump to conclusions and assume I’m going to talk about everything that’s happened with the series since my last post, that is not what this is about. I know how critical I’ve been with the series before on this blog, and despite that I felt I did the right thing and they have been the most popular posts on my blog, there is something about the posts that eventually got to me as a fan. Yes, I’m a fan of the series and explained my whole personal history with it before. But then I felt that I was criticizing it too much for a true fan, and I’m getting tired of it. Besides, everything has already been said, and even if there is ever more to say, I’m sure that whatever happens next with the series will explain itself at this point.

Unless something doesn’t explain itself and something totally unexpected happens, though, I might talk about it, just because there’s that part of me that still cares for the well-being of this property. But other than that, from here on in, any Diary of a Wimpy Kid-related posts will be in a more positive light, especially if the series shows some signs of turning itself around.

And with that being said, I want to give my opinion on the reveal of the 13th book, The Meltdown. From what I see so far, I will admit that I actually kind of like it. The cover illustration is great and the color doesn’t recycle The Last Straw‘s green, like The Getaway recycled Rodrick Rules‘ blue and Double Down recycled the first book’s red. Not only that, but the purple has something of a gradient to it, a first for the series, and the title font, which is the same as the “13” in the initial announcement poster, is a great finishing touch. Ironically enough, it may be my favorite book cover. Not only that, but the premise admittedly sounds promising:

When a wintry blast closes Greg Heffley’s middle school, it turns his neighborhood into a battleground, complete with snow forts, alliances, betrayals, and epic snowball fights.

So…I might change my mind and continue getting these books on the release date, even if I don’t end up liking The Getaway. The reason why I’m still unsure is because Double Down‘s premise was promising, too, and I don’t really want to keep encouraging this when Poptropica still needs Kinney’s help. But even Poptropica is marginally improving, so again…maybe.

But instead of discussing what’s happening with the series now, it’s time to get to what this post is about and look back on everything about the series that’s great. Which is why I came up with the perfect way to embrace this greatness by giving my own personal rank of the first ten books in the series. Yes, I’m doing the first ten books, rather than the whole series for obvious reasons. And of course, I’d like to give a heads up to some minor spoilers in the books before I begin.

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

#10: Dog Days

There was always something about Dog Days that rubbed me off the wrong way after I finished reading it, even as a kid. It was probably the first time I ever considered the possibility that the series could decline in quality. First of all, the book took place during summer vacation, and the books that take place during the time school isn’t in session are generally considered to be the weaker entries in the series. But that wasn’t what made Dog Days not work for me. I personally believe that Kinney can make it work, as The Long Haul was a better effort. But what made Dog Days not work for me, was that ending. There wasn’t a sense of a desirable finality to it for me compared to the previous entries. There were interesting parts, but they didn’t come together like the previous three books. Those books had compelling stories about conflicts between Greg and Rowley, Rodrick and Frank. This book could’ve tried something interesting with Susan, but it didn’t. Just Greg and Frank agreeing on how bad a comic strip was, and an album Susan made that didn’t really have anything that Greg could reflect on and appreciate – in other words, reflect on a good ending. I get it if this book is higher on your list, and if anyone wants to tell me what it is about Dog Days that works, I’d love to be enlightened. Although mainly due to incorporating elements of The Last Straw, the film adaptation was way better.

#9: Old School

The fact that this was the last book in the series before Double Down may play at least some factor in Old School‘s position on the list. It echoes Dog Days to an extent: Susan again wants Greg to put down his video games and go outside. But what makes Old School better than Dog Days is that it actually had a sense of a desirable finality to it, even if it could’ve been better. Susan is the focal point of the story, yet the focus eventually leans towards Frank for some reason. And while it eventually makes sense, it would’ve been great if it eventually went back to Susan, and Greg at least partly won his technology feud with Susan. I would’ve loved to see both sides of the argument understanding each other through the events in the story, rather than only Greg somewhat understanding and Susan not seeing where Greg is coming from at all. The technology themes could’ve also been emphasized better throughout. Even if this is what happened, when compared to other installments, the premise doesn’t stand too high up with the other books. (Though I did the math as the series progressed, and Greg should’ve been in high school by this book. He finally realizes he isn’t growing up around the beginning, which was hilarious.)

#8: The Long Haul

Remember how I said that the books that take place during the time school isn’t in session are generally considered to be the weaker entries in the series? Well, The Long Haul was one of those books, but I consider it to be the best one of these books in the series. (Though maybe The Getaway could beat it in a full series list?) Again, it’s better than Dog Days in how it depicts a faulty yet ultimately good summer vacation; Dog Days only showed a faulty one. It’s probably the whole road trip premise, which allows for a tighter and linear story, and it was cool for the Heffleys to get a new, if unorthodox pet. And the whole Heffley-Beardo conflict was rather frightening, with true stakes that honestly made me scared for the Heffleys every time they showed up, as well as conflicts with Manny and the pet, which made for a pretty good read. There aren’t conflicts between the main characters or lessons to be learned that are too deep, and it doesn’t end with Greg in the best scenario, but those things don’t stop the other parts that make it a perfectly okay entry. We don’t speak of the film adaption, though.

#7: The Third Wheel

This is pretty much the point in the list when the books in the series start to get really good for me. Although some parts of The Third Wheel had me scratching my head (the beginning reveals that Greg has some really good memory skills), it was generally a good enough entry. It takes full advantage of its themes of love, even if parents may consider love to be a questionable theme for children’s storytelling. I’m personally fine with it as long as the characters don’t act like adults, though the book doesn’t entirely succeed in that aspect. The different ways in which Greg attempts to get a date for the school dance was pretty fun to read, though (although couldn’t Holly Hills have returned aside from a love web Greg made?). Admittedly, it was somewhat unsettling to see Greg manipulating Rowley into getting him Abigail in one of those attempts, though both Rowley and Greg eventually get what they deserve. While the ending to Greg’s arc felt rather underwhelming, the events toward the end were quite dramatic. And when you put it together with Hard Luck, it ends up working way better.

#6: Hard Luck

Speaking of Hard Luck, I think the best part about it was that it’s basically the second part of a two-part story that begins with The Third Wheel. Unlike most of the books in the series, there is actually a sense of continuity to it, directly exploring the ramifications of the previous entry as Greg deals with Rowley’s relationship with Abigail. (And Rowley’s view of that relationship is quite hilarious.) Even better, Abigail comes off as an antagonist to Greg as a result of the events in The Third Wheel, specifically trying to keep the two boys apart. I have to give kudos to Kinney for getting out of his comfort zone with Abigail’s character:

She’s a little bit hard to write as a character because she’s meant to be a placeholder for a girlfriend rather than a fully developed character. It was a little tricky trying to figure out how to write for a character that hardly has any dialogue and not much of a personality. She’s just a stand-in for a threat to Greg’s and Rowley’s friendship.

There is also a pretty great side plot involving Greg’s family, and the title really fits the theme of the series as a whole. Of the three movies in the animated Diary of a Wimpy Kid film trilogy I proposed, if done right, the second film could easily be the best entry.

#5: The Ugly Truth

As it turns out, the puberty themes of The Ugly Truth has its own story behind it. You may remember when I stated how Kinney considered making The Ugly Truth the last book in the series, which would’ve actually seen Greg grow up. Of course, Kinney changed his mind and chose to subject Greg to the floating timeline. However, the puberty themes of the book remained, and Greg nonetheless didn’t cheat puberty without dealing with it in the same way as everyone else. Forget love, though – puberty is an even harder theme to tread in children’s storytelling, but Kinney pulls it off in the best way possible: through subtlety. But what makes The Ugly Truth really work is the challenge it brings to a fundamental aspect of Greg’s character: his desire to grow up and be rich and famous. Though relatable to today’s kids at least, it’s not the character’s best trait, and Greg realizes this in this story. And I think stories like this are important for today’s children, who often spend too much time in the future rather than the present.

#4: Greg Heffley’s Journal

From here on in, nostalgia plays into most of the entries on this list, which seems pretty obvious here. I had seriously considered giving the original book the number one spot, but I figured that this would be too predictable. But honestly, why wouldn’t I? It’s the book that started it all, the book that first introduced the concept of the flawed, unlikely hero in children’s literature, the book that spawned the adventures of many other fictional middle schoolers, the book that inspired this very list among many other things. It’s a classic story of the relationship between two friends, and how one imperfect kid tries to navigate the perils of middle school in the ways only he knows how, much like we all did. The film adaptation was pretty much how I expected it to be, aside from the surprise of original character Angie Steadman, who served as something of a foil to Greg. The way she navigated school life with such ease and nonchalance made her such a great character that it was almost upsetting that she never showed up in the sequels, nor in the book series to this day. And of course, who could forget that iconic Cheese?

#3: Rodrick Rules

I’ll always remember Rodrick Rules as a story about the development of a sibling rivalry. The whole book was about this one single stake – an embarrassing secret Rodrick had about Greg, and Kinney makes the wise decision to not tell us what it is right away to keep us on our seat. It really shows just how secretive Greg is about it, to the point that he didn’t even want to write it down in his journal unless he really had to. Again, it’s just one stake, but it’s really played up to the point that Kinney can get away with it. And when Greg’s slip-ups finally push Rodrick over the edge and make him spill the secret, the craziest thing happens: the story gets distorted to the point that Greg gets popular. And Loded Diper gets famous, but not in the way Rodrick intended. Greg actually gets sympathy for Rodrick, knowing full well Rodrick intended to hurt him for his mistake. So he decides to help him out with his science project. And you really begin to wonder why these two are still feuding on. In my opinion, the film adaptation was even better, and is my favorite entry in the original trilogy, due to smart changes to the source material that actually improve on the story. And that, in my eyes, is incredibly impressive.

#2: The Last Straw

There’s something about The Last Straw that I always thought was just so great. It’s about realizing who you are as a faulty, realistic human being versus facing the horror of being transformed into a person you don’t even know anymore, and what your life will be like from then on out. It’s about not understanding the differences in others to the point of wanting them to change versus realizing the benefits of what makes that person different. It’s a story about father and son that’s relatable for many – that dad who’d love his boys to be strong, dedicated young men compared to that sensitive, imperfect boy who just wants to be left alone. Frank, upset with Greg’s nonsense, threatens to send him to military school in his attempt to toughen him up. Greg tries to impress him at first, only to make things worse to the point that he actually accepts his fate. The stakes get pretty tense, until Greg’s mishaps end up helping Frank in the end.

There’s also a side arc involving Greg impressing Holly Hills, the formal introduction of his most well-known love interest, and even though he fails with that as usual, the rest of the story was so great that I didn’t really mind too much. The ending was one of the most solid endings in the series (quite literally), and the introduction of Trista was quite pleasing and promising. At least until Dog Days kicked her to the curb… 😦 Childhood dreams shattered aside, although the book never truly got a direct film adaptation, the book’s plot was integrated into the Dog Days film, which, given what I said about Dog Days earlier, was a really smart move. Not only that, but things between Greg and Holly ended up way better.

#1: Cabin Fever

There’s a reason why Kinney won a Best Author Children’s Choice Award from the Children’s Book Council for Cabin Fever. There’s a reason why the book was nominated for a 2012 Harvey Award for a Special Award for Humor in Comics. There’s a reason why Kinney considered adapting the book for Greg’s first full-length animated venture. That’s because Cabin Fever was just that good. That’s even more impressive considering that its predecessor acted as a possible place to end the series. For me, Cabin Fever even transcends the nostalgia factor I get from the first three books, simply because it does something with Greg that I think even those who are more critical of his character could appreciate: it makes him selfless.

In his attempt to get money, he accidentally commits a crime with Rowley that he more than pays for, and fully takes responsibility for it as he should have. He is fully aware that what he did was wrong, and that he could get locked up for it. He actually considers the well-being of others for the holidays even as Manny freezes him in the house, even as he fears the cops catching him on his way to the Toy Drive. And on top of all that, the snow he shovels in his continuous attempt to get that money actually ends up feeding many people who are much less fortunate than even him. He still makes it clear that this wasn’t his intent, but he was more than happy to lend that helping hand. (Dang it, why wasn’t that animated movie made again? Kinney considers himself a cartoonist, right? It could’ve held a candle to a Peanuts special! Peanuts! But I digress.) 🙂

Well, that’s my personal opinion on the greater part of the Diary of a Wimpy Kid series. While I could say what was wrong about Double Down and The Getaway when I read it, I won’t do it unless you’re curious enough to the point that you really want me to. But this is it for now, and who knows, I might make a similar list like this for other children’s book series in the future.

But for now, stay wimpy, folks. 😉