Ah, the caricature. Seems there’s no easy route to grasping it; like everything else, it’ll just take practice. Before tonight’s attempt, I watched some YouTube videos by this kid Sycra Yasin, who makes everything look way too easy. He seems to have many different approaches to caricature, but the one I latched onto was breaking the face into geometrical planes. For example, here’s evidence, roughly traced from a photograph, of how I earned the childhood nickname “Squarehead”:

Of course, you wouldn’t really sketch it out like a creepy kabuki mask, but the point is, breaking down a face like this gives you a sense of why certain features fall in certain places, much moreso than the typical cartoon method of tacking 2D features onto 3D spheres.

That’s not to say I got it right, but I feel like I’m making progress. And I’m eager to learn about other methods of approaching caricature (paging Aunt Susie).

Also, I’m too close to the current subject (and he keeps eating all my food), so if you’d like to volunteer to be amateur-caricatured, let me know.