Supervillain Dad

I've had an idea in my head for a long time about a family of super villains (given my intense love for the Incredibles) who had once been the terrors of the earth and were now raising the next generation in hiding. I'm planning on making it into a book, though I'm not sure if that's the right format yet. I've developed them a lot since then, but I only recently took the time to visually design a few of these characters. The man in the first drawing, the head of the family, the paterfamilias, was known in his prime as Judge Executioner, Hangman to his friends. Imagine his costume there as almost all-black and grey. I imagined his hood as a cross between an executioner's mask and the hoods one would put on someone they're interrogating, etc. I used quite a few references when designing him until I finally got what he looks like in my head. This might not be the final design (it might be more like the smaller ones), but it's much closer then I had originally.
The fourth image is a doodle I did in class when I was trying to figure out what the mask should look like. The one here is scary, sure, but I didn't feel like it evoked Hangman. However, the drawing itself is of Hangman's daughter Moira when she finds his mask in his old stuff. I liked the idea of that moment so much I kept it here (whenever I see it I kind of hear the music from when Luke is taking Vader's mask off). 
My mom has noted on more than one occasion that I have a strange fascination with villains. I think a lot of which just comes from the fact that they're different from other people. I think that's a lot of what I'm going for with this story. God's will be done, who has mercy on the righteous and the unrighteous, the good and the wicked. Thank you for having mercy on me.