Long overdue

Here's the latest thing I've been working on: a caricature of my girlfriend, Lexie.

It was interesting to colour, because I felt the original lineart had a fun, cartoony feel to it that I didn't want to lose. So a couple of hours into doing a more realistically rendered painting like I`d done for Ringo, I scrapped it because it just wasn`t working. I decided I'd rather attempt to emulate the look and feel of the art stix we use at Wonderland, but I'm still not super confident with those, and I wanted this to be good (it's a gift after all). Overall, I like the way it looks, and I feel the grain filter over top nicely replicates the texture of art stix on paper.

Part way through the painting, it was really bugging me, because I felt like I'd somehow lost the likeness. Looking at the lineart, I still felt like it really looked like her, though. After staring at the two for a long time, I realized that, even though I knew I had brought the gums down really far, in black and white it read as two rows of teeth. Bringing the teeth up did end up helping, but there's still something that's a bit off about it, specifically the eyes. I dunno, let me know what you think.

Update:

UPDATE 2:

This morning I woke up and got right on the cintiq, because this thing was still bugging me. The eyes! The new eyes I did yesterday were drawing too much attention away from the mouth, which is really the focal point of the drawing. Also, they just didn't look good. The new eyes are smaller, and back to the extreme squint, but I brought some of the elements from yesterday's eyes in to make them look more like the subjects than the original. I realize now what the original problem was: I was on the right track by having the eyes closed, but they weren't "Lexie's eyes".

Also, I reduced the contrast by bringing both the shadows and highlights closer to my middle tone. I know that normally contrast is what brings you in and creates an appealing composition, but I felt that this drawing is really more about the subject than interesting lighting, and I think the forms are described well enough without the contrast. Further, I reduced the blush I had on the cheeks and nose, and made the colours a little cooler in general, so it's closer to the subjects real skin tone.

Da Vinci was right, art is never finished, it's abandoned.