Painting a styilized character

I don't really know if this counts as a tutorial since it's really more of a general overview of my technique for painting a digital caricature. I started this because enough people have asked about how I create these types of paintings that I figured it would be easier to put it in a visual format than trying to explain it. Even though I created it in Painter IX.5 the technique is easily transferred to other drawing programs and I've used essentially the same methods in traditional media such as oils and even Acrylics.

As soon as I sat down I discovered how difficult it is to explain the process of creation because it's not one thing but dozens of individual steps and many questions are raised. The problem is that few of the answers to those questions are straightforward. Something as simple seeming as, “How do I pick good reference photographs to draw from?” can easily spark a heated debate. But it's a question that should be asked more often than it is considering how often photo reference is used poorly. Other questions are far more abstract like, “How do I know when something is finished?” I've watched good artists spend hours agonizing over details so minor that nobody else will ever even notice them.

One question I've gotten several times recently is, “How do you stylize or caricaturize someone and keep them recognizable?” Short answer: exaggerate, don't invent. If someone has big ears make them bigger, a small nose then make it smaller, squinty eyes then make them squintier. But if you just give someone a buck-toothed overbite when they don't have one then people are far less likely to recognize the person your stylizing.