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I don't know if it's any consolation, but the awkward smile that replaced the blushing sprite on Asterion is my absolute favorite in the game. I suppose that's probably not what you're talking about, so Luke's wild bug eyes that can be seen even when wearing sunglasses is up there, too. Is it just so it matches your current style and shading when doing new sprites?

(+3)

The one I was thinking of was the Asterion one, yeah.
Basically the way sprites were set up (a simplified explanation) was

  1. A layer with the fur as a solid color and all the color details like Asterion's muzzle and nails
  2. A face layer, with facial expressions
  3. A lineart layer, which included the shading done in black and white
  4. Then all the clothing layers on top

Now this had two big disadvantages: 1) Shading with black and white (as opposed to using desaturated colder hues, and warmer hues with higher saturation, respectively) looks fucking terrible and I have no idea why I did that for years and 2) since the clothing layers have to go on top of the expression layers and the lineart layer is fixed for each pose, Asterion's muzzle was set at a fixed position. So if I wanted him to open his mouth to laugh, the muzzle would still be as wide as it was when his mouth was clothed, which doesn't look great. It severely limited his expressions.

So, after doing that revamp, the layers are set up like this:

  1. A layer with the fur color and shading, this way each fur color has specific shading and lighting colors (eg. brown has a more saturated orange for lighting and desaturated reddish purple for shading)
  2. A layer with all the lineart and details in one
  3. A bunch of the clothing layers like neckwear and upper body clothes
  4. The face layer, which includes the edge of the muzzle. This way the mouth can go over the upper body and neckwear layers and Asterion's muzzle can change shape easily
  5. The rest of the clothing layers

And... I had to revamp all of those, 4 times, one for each of Asterion's poses, and modify some of the clothing sprites to accomodate for the missing space where the muzzle used to be. Well, 4 and a half considering that Asterion's arms change on the pissed off sprite and the surprised sprite. And all the faces were redrawn to fit my current more expressive style.

So yeah, you can see why this one makes the top 3.

(+1)

I mean, the clothes in general are a lot and something a lot of VNs don't have to deal with. I think the closest is Extracurricular Activities and they all follow the same basic shape except for special occasions, where they typically have like a month for a single character route. And none of those are player chosen, so CGs don't need to consider what a user has chosen outside of the MC hair and skin color. Like, the amount of work you already do seems exhausting even before hearing that process. It makes sense for the story and getting players into the headspace of the master, as well as showing how much control they have over him superficially to imply just how much power they have in general, but it's definitely a lot. Seems like the new workflow should be better for not having to get creative to get the expressions you want, though. But yeah, no surprise it's in your top 3 after just how much you had to redo.

(As for shading, I used to digitally restore photographs from a few major companies archives at my old job. Since we would sell images as needed the idea was we'd fix up the image and then it would always be done. It meant less time to correct if I would see errors years later since we'd also do the often large prints ourselves so you could see every imperfection and digital mark. Eventually I had it down where I could over sharpen to adjust for the smudging with ink to look sharp and make it so all of my healing wasn't noticeable, but some of my earlier work looked awful and I'd sneak in reworking when I could. You just get so used to a process that when you find something better, if you're forced to keep seeing your previous work you can't help but want or need to redo it, especially if it's going to be mixed in with your more contemporary output. I am happy to not have to worry about that anymore lol. )

(+1)

I think looking back at older work and cringing is good and healthy, it's a way to know that you're improving. I'd be more concerned if I looked at old drawings I made and DIDN'T cringe, because it means I stagnated.

Definitely. There's a lot of photography I have online that's fucking embarrassing and makes me laugh, but I wouldn't ever get rid of it because of where I got from that point. It also helps if you're in a rut to remind yourself of how different things are now. It's just part of the creative process. Always another cocoon to break out of.