I had to throw this together quickly because it is grossly out of date and I'm working on something else with these folks (or, more accurately, something I've done before, but ever so slightly different!)
A couple of years ago (god has it been that long) I decided the 2nd cast needed yet another overhaul, but this may indeed be the last! Or near enough. I 'teased' about it on Tumblr but never actually followed through.
So what's different?
The Drawing Man: A character who isn't really as prevalent anymore but when he does appear, it'll be like this. There were two reasons for the changes, the first is that this character represents me, so this now looks more like me but more importantly, I wanted to accentuate the distinction between a "real" person and the toons so I tried to achieve this by making his as uncolourful as possible so that the toons stand out more in that respect.
Lunis: The problem with Lunis was always everything. I drew a cartoon moon and liked the look of it so recruited it in the team. As I started trying to exaggerate him he eventually stretched into a shape which couldn't really be portrayed from any other angle than the side. His lack of limbs was the catalyst for his telekinetic abilities but it meant that he couldn't gestate or easily be portrayed doing anything. Without the ability to point or kick or strangle he was severely limited in his readability, which I understand can be quite important for cartoon characters. Finally I liked the idea that his sinister smile should be permanent, so as to accentuate the sinisterity, essentially making him a completely flat and lifeless character.
So I rounded him back out (he is now somewhat hemispherical, also allowing him to work in three dimensions), gave him some limbs and an extra eye, which wasn't really necessary, but it allows him to emote better and makes a reference to his supernature.
Drizzle: Drizzle hasn't really changed much. Early on I made him more cheerful and a white cloud instead of a black cloud (though that can still change with his mood) but ultimately he's stayed the same. This was something that worried me, I wasn't sure if the design was strong enough since it was so simple. For this image I constructed the notion that he has "hair" which changed depending on the weather it represents, like a big sun afro or the tornado pompadour. I might still use that, but for my most recent drawings of him I actually took that way again. I also tests a few "bodies" for him but nothing really looked right. Eventually I started looking up what other people have done with "cloud creatures" and instead I was reminded of the practice of finding shapes IN clouds, so NOW I'm thinking of maintaining his simplicity because I still think it works, but giving him to option to morph his body for certain actions/jokes.
Quartz: Since his inception Quartz was always supposed to "live" in a crazy cuckoo clock but I never managed to implement it anywhere and the problem with his previous designs was that he had a very small torso with a lot of this appendages coming from it (neck, wings, leg, tail, key) which was a bit too busy and obstructive. I would even frequently forget to draw his tail because of this! So for his new design I built the clock right into his body which gives him more stability overall and makes it more obvious that he's a cuckoo. Also as the simple, naive character it affords him a bit of clumsiness.
Crumbs: Crumbs was a pretty confident design from the start so there wasn't much that might have ever needed changing but I did alter the shape of his eyebrows into something more befitting of an icing design and to make the head more coherent overall.
Brookyln: There also wasn't much to change about Brooklyn but I revised the design of her shirt slightly and reduced the number of colours in her scheme which hopefully makes it stronger.
Zeppelin: Zeppelin has had the most redesigns despite the fact that almost all of his details have remained the same. This is because I have never been happy with his proportions so they've never been consistent. This was another one where taking away some spindly limbs made for a more solid overall shape.
The Flying Buttress of Venison: Another one which has stayed mostly the same, a lot of the changes here were simply small cosmetic amendments for the sake of efficiency, but it did get a nice pair of eyebrows in the process!
The "project" I'm working on is going back to the alternate "forms" of the toons, an idea which seemed pretty original at the time but it looks like a number of people have done something similar in recent years.
I'm still going to do it though, mine isn't quite the same as some that have come before it and now quite a few of them have been redesigned to various degrees both to suit these newer "standard" forms but also because certain aspects of them weren't working but now I think I'm happy with all of them! So expect to start seeing them soon too.