Every once in a while I get asked to do some caricatures for clients. Typically it's for a website or brochure where the they use the images with a fun bio. My style doesn't really work great for caricature because most of my people all look the same to me.
This batch was kind of hard because they were all young guys, in good shape with short dark hair. It makes my job easier when everyone has at least one distinguishing characteristic, glasses, mustache, red hair, bald. Anything. So to help out on this one, we went with hobbies and interests.