I was recently commissioned to do two designs for t-shirts for a company in London that do Jack the Ripper tours.
The first is a playing card design, the Jack of... Ripper I guess
I wanted to make him pop out of the card, like he was coming for you and added a little street scene behind him to explain the light source on him.
This second one was to look like Jack had split you open and lifted your guts out, gross but REALLY fun to paint, took me right back to my days as a kid reading 2000AD and staring at all the gross details in the stories :)
I tried to keep it a little comic booky so as not to be to disturbing but still look realistic enough to be recognised.