How to learn how to draw caricatures
When I was a kid, I studied the great masters of caricature art, Mort Drucker, Angelo Torres and Al Hirschfeld. You can Google these artists or find some of your own. All artists start by imitating their masters, then they find their own style. Carry your sketchbook around (if you aren't already), and draw your friends. By the way, if they want to take the drawing, give it to them, that is a good sign. If you offer it, and they say, "uh... no, I'm already carrying too much", don't be discouraged, that just means that you need to practice more, in private.
To capture a likeness, you will have to observe and be aware of major shapes. Faces aren't only about eyes and noses and ears. In fact, most caricature artists have just a few eyes, ears and nose shapes that they draw. The key to capturing a likeness is to get the shape of the face, and the proportions, correct. If you have only drawn by looking at a photo, doing a drawing from life will be a challenge. Yes, I know it sounds corny, but begin with drawing a still life, that is, the old "bowl of fruit" or the objects on your desk. This will actually be the most difficult part of the entire process, and it's also why most artists resist it. It is very different drawing from real life than from a photograph. When you draw from a photograph, it's already visually flattened for you, the shadows never move, the subject holds still. Drawing from life means that you have to see it all in your "mind's eye". If you are self-conscious about asking people to sit for you, draw your dog, or go to the zoo.
A teacher of mine once told me to "spend more time seeing than drawing". If it's not convenient to have your sketchbook in front of you, for instance while driving, you can still be seeing like an artist. The drawing is done in your mind, putting it down on paper is just the last step.
Posted by Brad Hall