Back when TheSwain.com (a) existed, and (b) had a forum and not a 403 page, there was a little organised art thread where each month one user would draw avatars for in theory all the other regular users. I ran way over time and didn't finish all of these until the intended month had elapsed, because I insisted on full colour and shading and coming up with a specific gag/reference/unique idea for each one, while also potentially riffing on their existing avatar. From top left to bottom right is the order I made them probably. The Taliban one is Señor Sausage, whom I culturally misrepresented for the second time after my "Victorian" picture. Misspelling the user "Syntax" as "Sytax" was a deliberate joke because someone else had done it before, but he didn't get it.

Obvious influence at the time aside from The-Swain/Blockhead is Cyanide & Happiness circa 2008-9.