Ok. Let's start talking Cartooning. And let's open the festivities accordingly: With a carricature portrait of Mad Men's Don Draper character.
There is a general misconception that caricature is all about finding a defining characteristic of a person's face and really enlarging and elongating it. While in some cases that is close-to-technically true, it's way more of a balancing act of re-arranging one's features and proportions in a new narrative, one that somehow captures the essence of a person's face more accurately than a photo. Actually, the best description I 've heard of a caricature is "a portrait with the volume up".
I can't recall who said that, but this and many more gems of cartooning wisdom can be found in Tom Richmond's excellent book "the Art of Carricature". a thorough and illuminating study on the subject.
So what is my personal way of tackling this unique kind of portrait? Apart from the essential technicalities, I have one secret recipe : I always have a double reference system: On the one half, I have on my desktop photo reference of the person I want to "portray with the volume up". On the other half, I close my eyes and try to recall the mental impression the face of the person has left on my brain. Like, if I had no photo of said person at all, how would I draw him from memory? Think of it like I am both the eyewitness of a crime, and the police portraitist both at once. Then I try to reconcile the two versions, adjusting here and there until I am happy.
If I am successful, the subject of my art will be happy too.
If I am REALLY successful, that same person will hate me for life.