I made this for a presentation I did on character design. The presentation was about an appoach to character design I've been developing for a while now, with the help of others at Avalanche like Todd Harris. For the presentation, I took people through the steps of making a character appealing for a specific audience and purpose.
I decided to take an old drawing of a torture specialist and try to make him appealing to a 7 to 9-year-old audience (fun!). I picked this drawing because it's not necessarily a bad drawing, and he might even be appealing to an older audience---but the point of my presentation was to emphasize that design is different than drawing and that appeal is subjective depending on the audience.
So in order to make this guy more appealing to a mixed 7-9-yr-old audience, I made up a backstory that he used to have a medical practice, but he went out of business because his patients were creeped out due to his hairless condition. He picked up the torture gig on the side just to make money, but unfortunately discovered his latent fear of needles and a tendency to faint at the sight of blood. Then with the audience and this personality in mind, I essentially applied various design principles to him and he sort of evolved naturally.
This is the beginning character (left) and the end result (right). Ask your 7-year-old daughter or nephew which one she or he likes better so I can find out if I was successful.