I enjoy to warp and stretch portraits as much as I enjoy trying to render them accurately. The art of caricatures is a fun and creative process that really allows each person to bring their own strengths and styles to the portrait.
When doing a caricature I start by looking at the persons features and just getting that first ‘flash’ impression of them. You might see that they have a square head, a long face, sunken eyes, a big nose or ears, ratty hair… It doesn’t matter, just that each person has their own distinct appearance. Often what I find compelling and interesting is the flaws in a person, not that you are making fun of them by drawing a caricature but that these things are what makes their face fun to draw and interesting to look at. By extension then, exaggerating their ‘flaws’ can be a fun way to come up with some really nice proportions and features to draw.
Accentuating the blocky shapes and the overall square shape of the head.