Hi Ami, That's a great question. Caricature artists are really great at this. It may not seem like they are using the Loomis or Reilly methods, but often they are, but are exaggerating things to get that caricature effect. In fact, I know a lot of great movie poster artists used the Reilly method to get likeness, and to exaggerate it. There are often specific characteristics that each person has that are important to look for when trying to capture a likeness. Again, I would say, see what the caricature people focus on. Think about a political cartoon of say Barrack Obama. They usually give him large ears, and pronounced eyebrows. They get a characteristic shape of his head. Etc. To develop these skills, the first thing is a really good understanding of the "standard" proportions of the head. Then you can look at the person you're drawing and figure out what is different than standard. Are the eyes a little closer together? Is the jaw a bit bigger? Tools like Loomis are really for idealized heads. Most of us are not so perfectly formed lol! Learning to spot the differences from an idealized head to a real head is half the job in learning to do likeness. Hope that helps.