I'll start: For one, I consider only books 1 to 9 (and a little bit of book 10), plus the Do-It-Yourself Book as the original canon. They, in my eyes, are set in the 2000s—either from 2006 to 2009, or from 2007 to 2010. Either option works. (Shown above.)

I also chose to assume that books 1 and 9-14 are in an alternate universe, in a different timeline.

This second timeline would go like this:

Diary of a Wimpy Kid: September 2012 - June 2013

The Long Haul: June 2013

Old School: September - October 2013

Double Down: October - November 2013

The Getaway: December 2013

The Meltdown: January - February 2014

Wrecking Ball: March - June 2014 (I chose to assume that the ending was non-canon, and that they actually moved.)

After that, starting with The Deep End, the books are completely non-canon.

In that sense, Greg would have been born in either 1994 or 1995 in timeline 1 (seeing as he was 12 in the first book) and in 2000 in timeline 2.

I know DOAWK is officially timeless, but I think it's fun to date the series.

Image related

I’m way late to the contest but it was on purpose, anyway who looks the best out of the four because all of these, even the classic wizard Greg looks so expressive and SO GOOD GOD I LOVE MAKING HALLOWEEN ART

Greg mentions in The Meltdown that Rodrick won't go anyway near Latricia because she used to bully him when he was his age. Rodrick has a lot of friends as shown in his party in Rodrick Rules and he has some friends who are part of his band Loded Diper. Rodrick is also friends with a big guy named Ward who provides security for the band.

Rodrick has a reputation for being a prankster and a troublemaker so I don't understand why Rodrick and his friends don't just jump Latricia for bullying him when he was Greg's age. Latricia Hooks is 6'2", big and strong but she can't fight back if she gets jumped by multiple people at once. I really hate Latricia for bullying Rodrick and I don't get why Rodrick and his friends don't try and get back at her.

Literally all the non-bully students (and those who were already there like Greg or Rowley) have heads like this

WHAT HAPPENED TO BACKGROUND AND NEW CHARACTERS???????? seriously, the new artstyle is awful. we've got people with potato fries noses and oval heads, they ALL look exactly the same. ik jeff wouldnt waste time coming up with unique designs, but now we've got greg drawing in rowley's artstyle but with noses and ears

If i were to make it then this is a heads up on the artstyle I'm using!!! (And hand refrences)

Sorry for the empty half-page near the end, I thought I would cut off the chapter at it, but I decided it would be too short if I ended it there.