Here's where we currently stand. Going with a neo-noir theme, I've generally drawn the images from the 1940s, with a few from the 30s, and 50s, and a couple of later images that were taken with that era as their inspiration. The thing about the era is that most of the people in Film Noir are white, with the males being slit into debonair types or hard boiled detectives, while the females are attractive dames and femme fatales. I've deliberately made sure to counterbalance this with a range of images of non-white characters in the mix.
Now I just need to make duplicates of these images depicting the characters in prison.