So in RPG Maker MV (the program I'm using to create the game) there is a character generator allowing one to make tons of people that don't particularly look like Sam and Dean. The clothes are mostly knight/wizard/princess type outfits and the hair is over-the-top anime style, for instance blue spikes or green hair down to the feet. It makes sense that in a game where you may have dozens of tiny characters running around, they have to be distinctive. But I only anticipate having three, so I can put some effort into personalizing them with subtle details.
I'm not skilled enough to draw them from scratch. Tiny pixel art is tricky. If your sleeve is three pixels across, do you use one of the three pixels as a black outline? Do you make lighter blue on the sides and dark blue in the middle to show the elbow crease? Or darker blue on the sides and lighter blue in the middle because that's where the highlight should go? I don't know. So I'll use the character generator to make some guys that vaguely resemble the Winchesters, and tweak from there. Right. Luckily there is a "business suit" kind of outfit that I can adapt.
Original non-Deanlike guy:

Dean's Purgatory outfit:

Ha ha! How did it turn out? I may fool with it more later but for now I declare it satisfactory.



How about Sam? Well, having made Dean I notice there is room for the characters to be taller if they don't have a mountain of anime hair on their head. The standard height for this game system is 48 pixels high. Sam can be at least 2 pixels taller than Dean, yay! But how? Hm, I don't want to stretch his head. So here's what I do: I pop his head off and move it up, and then stretch his body to fit the space, and then clean up any resulting weirdness. Looking plausible! Okay, Sam can wear whatever he wants. Some red and white plaid? Hm, Sam hair... The pressure... Something like this?

Yay, now xoferew is done making Sam and Dean for the game, right? Ha ha ha, of course not. One nice thing about this game making program is it also has sprites for all kinds of battle moves, lying down dead, etc. Assuming one used the character generator.

Yikes, this will take forever to redo all these little guys to look like Sam and Dean! *xoferew cries.* Well, I'll do that another day.
There are also the big faces that will be used for dialog. Very important for making the game come to life. I've already made one basic one each for Sam, Dean, Cas, and Kevin, but Sam and Dean will need at least six emotions each and Cas maybe three. That's a different kind of digital art. I can make it as big as I like and then shrink it down to size. It's fun but time consuming and I'm not good at sticking with the same style through a series of pictures. I'll save that for summer vacation probably.
But what about Cas? Where is poor Cas? Sadly, not made yet. Maybe next weekend, Cas! Oh, but I did make a damaged version of Dean! ^_^

Here are the brothers together. The animation isn't aligned perfectly because I just threw together a gif to show their relative heights. The game will take care of the animation smoothly.

Please feel free to make suggestions. Are the boys recognizeable? Have I committed an unforgiveable sin against Sam's hair? Is it terrible that Sam's jacket and jeans are the same color or does it give him visual cohesion? Ha ha, visual cohesion. I just made that up. Pretend it's a game making term.
Thanks for reading!