Drawing Children’s Book Characters In My Style: Diary of a Wimpy Kid Edition

Hello everyone, and as you can see, you’re probably surprised with the new direction the Drawing Children’s Book Characters In My Style series has taken. Back in Round Three, I decided that I would start doing supporting characters for the properties I’ve already explored because I was running out of ideas for characters in which I can represent a lot of properties in a single round. So I decided to tackle the supporting cast of none other than Diary of a Wimpy Kid first in celebration of the release of the thirteenth book in the series, The Meltdown.


With that being said, I have officially decided that I am indeed getting The Meltdown today, and staying loyal to this series. This is because my perception on the latest developments with the series has changed since the announcement of The Meltdown. Yes, I still think that Kinney needs to care more about Poptropica, that Diary of a Wimpy Kid needs to be a StoryArc property, and that Greg’s next movie needs to be good and animated. But as for the book series itself, it appears to be improving since Double Down. I have finally read The Getaway a while ago, and it’s a pretty okay entry that’s even better than The Long Haul, making it the best of the non-school set books in the series. If you want to know more, I have written the reviews for Double Down and The Getaway some time ago, which I’m leaving on my Goodreads. And I also read the preview for The Meltdown, and it’s pretty promising. Of course, we have yet to see if The Meltdown itself keeps the quality of the series consistent, and that we never get a book quite like Double Down again.

Anyway, like I did with Greg himself, for most of the characters in this round, I will be referring to the books for their basic features and the films for the details. As for color, I was initially unsure if I wanted to keep with the black and white style that I did with Greg, but I decided to do so in order to make the most authentic versions of the characters.

And of course, the usual rules before I begin:

  • I’m only doing children’s book characters – meaning characters featured in books intended for audiences up to 12 years of age. Even if a character first appeared in another medium such as a comic strip or a game, I will still consider the character to be a children’s book character.
  • I’ll usually do ten characters per round, though I might do more or less depending on what I’m feeling up to doing or how much time I have on my hands. If multiple characters are often associated together (i.e., Jack and Annie from Magic Tree House), I will consider them as one character for the round (featured in the same image).
  • Since there are characters I will probably end up ignoring/not acknowledging, I’m open to requests to do these characters, as long as they are children’s book characters. I might also consider some young adult characters depending on the property.
  • Some characters have styles that are specifically distinct from mine, so some characters will look more differently in my versions than others. Depending on how distinct the style of a certain character is from mine, I may ignore that character on purpose, unless requests entice me to challenge myself.
  • Although I am creating a new interpretation of these characters, I will try to maintain the essence of their original designs, if there are certain features about them that in my style wouldn’t look the same. For example, I generally don’t give my characters dots for eyes, but if I am drawing a character with this trait, I will simply make the irises bigger.
  • As usual, if you wish to share my work, you may do so for as long as you credit me. If you wish to use my work in any way, feel free to either comment or send a contact form on the Contact page.

And so let Diary of a Wimpy Kid Edition begin!

Rowley Jefferson, Diary of a Wimpy Kid

I knew that when it came to drawing Rowley, I had to place him in a fun, joyful pose. I thought about the pose he makes whenever he says “Zoo-Wee Mama!”, which this drawing takes influence from. His mouth had to be open no matter what, or it wouldn’t be Rowley, and since I often bear all the teeth of my characters when their mouths are open, I added this element to Rowley’s two bigger front teeth. A cheerful sight, isn’t he?

Fregley, Diary of a Wimpy Kid

I have to admit that Fregley ended up better than I expected. His pose isn’t based on anything of his in particular, though I mainly wanted to evoke the idea of Fregley being this kid who wants to have some fun, but he only makes you want to run away at the sight of him. The character has always been a hallmark of Diary of a Wimpy Kid‘s bathroom humor, and I really wanted to translate that in this drawing. Ugh… 😉

Rodrick Heffley, Diary of a Wimpy Kid

You may recall this pose from the Dog Days movie poster, with some notable differences, which I think is the best pose Rodrick has been in. It really shows the character’s wild nature as a rebellious teenager and heavy metal drummer. The foreshortening was a little tough, but the pose was too cool to not do. The five strands sticking out of his hair refer to his hairstyle in the books, while I added his drumsticks and his Loded Diper shirt. I could’ve sworn that there was another version from 2017 to draw from, though. Eh, must’ve slipped my mind. 🙂

Manny Heffley, Diary of a Wimpy Kid

He locked up and froze his family inside his house, collected hundreds of dollars, and hijacked a snow plow on Poptropica’s Wimpy Wonderland Island! And he’s ownwy thwee! With the notable exception of the head, drawing Manny was pretty easy. Manny’s head shape is notably different from the other Heffleys, who have rounder heads that fit closer to my style. So it was a matter of reshaping the head to suit my style while retaining the basics of the original shape. I also knew that his pose had to evoke both the mischief and innocence that Manny is known for.

Frank and Susan Heffley, Diary of a Wimpy Kid

Greg’s parents were a fairly quick job, especially in the case of Frank who is in a simple serious pose with that watchful, disapproving eye of his. His hair is mostly taken from the books with a strand or two taken from the films. Susan was originally going to do a simple thumbs up pose, until I remembered just how different she could be from her husband and based her pose off her Dancing Mom alias. My decision to make her glasses transparent also came from the films. This admittedly made Susan a lot more entertaining to draw than Frank, but that’s how the cookie crumbles for these parents, I guess.

Chirag Gupta, Diary of a Wimpy Kid

He must be happy that I don’t think he’s invisible, huh? Chirag has a few notable differences between his book and film counterparts, with his drawing being a fusion of those features. He has a lot less hair in the books compared to the films, so I did a balance between the two while giving some attention to the top. He also has a distinctive nose in the books which I acknowledged, while not oversizing it at the same time to prevent him from becoming a little too visible, if you know what I mean. 😉

Holly Hills, Diary of a Wimpy Kid

I’m not going to lie, I couldn’t wait to do the last two characters in this round. I wanted to respect Holly’s hairstyle from the books while at the same time embracing the longer hair in the films, so I made Holly’s hair just a little bit longer. I put her in a striped skirt as a homage to her appearance on the title page of The Last Straw. Good thing I kept Greg in a separate round, huh? 😉

Angie Steadman, Diary of a Wimpy Kid

And we conclude this round with a more special entry, a character who hasn’t yet appeared in the books at all (No, The Movie Diary doesn’t count), the negative head of the school paper that knows how to survive middle school like a boss: Angie Steadman! If you learned something today, a drawing of her showing what she would look like had she appeared in the books exists, which appears in the credits of the only film she has appeared in. I used this as the “book” reference while of course referring to the film. I knew that her pose had to reflect the assertiveness that Angie is known for, as if she knows just how well she can survive middle school and doesn’t mind the whole world knowing it.

Well, that’s enough wimpiness for one post, if you ask me. With these particular rounds, there’s a good chance I won’t make any new drawings of characters that come from the property I focused on. So if there are any other characters from the property that I didn’t draw that you want me to draw, in this case, Diary of a Wimpy Kid characters, I won’t mind requests to draw them. In regards to characters from other properties I haven’t explored that are featured in groups, I think I’ve decided that I’m not going to present them in any rounds. Rather, I’ll send them straight to the Artwork page for your viewing pleasure after they appear on my DeviantArt. I’m also going to be changing up my Artwork page accordingly with the new abundance of drawings this round has brought to the blog.

As for the next round? Well, we’ll have to see what comes of the next major event in the world of children’s literature. Depending on the property that event is focusing on, the supporting characters of that property will be the next to get my art style treatment.

Enjoy The Meltdown, folks, as will I. (Hopefully). 


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