So let’s get to it. Here are four ways to draw cartoon head.

1. Simple Shapes
This method relies on using basic shapes to form the overall outline of a head.  More often that not, those shapes are rounded, as in a circle or ellipse.    Having said that, a certain kind of character type comes comes across when using something other than a circle.  A head drawn with a square or rectangle will feel different in nature from a head drawn with a triangle.
Using a Simple Shape is done with heavily stylized characters, especially in cartoons that are animated with Flash, Toon Boom, or some other 2-D computer software.

2. Complex Shapes
These are the classic “Disney” style heads, drawn with simple shapes layered one on top of the other, and drawn very, very lightly with a pencil before being traced over with another, heavier pencil line or ink.
For a person (or otherwise humanoid character), this takes the form of a circle or ellipse, and another, smaller, ellipse or rounded triangle shape.   This arrangement duplicates the cranium and jaw of a human skull.
For an animal, the arrangement is slightly different.  The larger, “cranium,” shape is a cube, and the muzzle or mouth area is either a smaller cube, a tube, or an ellipse.  The “muzzle” sticks out from the larger cube shape, and forms the basis for the nose and jaw.  This is easily seen with a dog or cat, but can be used for just about any animal except a bird.  For a bird, the larger shape is an ellipse, and the beak is a cone or triangle.

3. Freehand Details
This is more of what I call a “doodling” exercise, because it relies of concentrating on a detail first, and drawing outwards.  I liken it to drawing  a tree, starting with the smallest leaf.  The idea is to start off drawing a single feature, say, a nose first.  From the nose, just below that you draw a mouth.  Just above the nose, and to either side, you draw eyes.  Then ears, then the overall shape of the skull, then a neck, and so on.
I would actually call this a more advanced skill set, because it is very easy for a beginner to not place the features in a way that suggests the structure of a skull.  A practiced cartoonist can “eyeball”, or sort of guess, where the proper spot is to place the mouth, the left eye versus the right eye, and so on.  I wouldn’t recommend that a beginner start with this method, however.

4. The Potato Game
This combines the best of drawing with Complex Shapes with Freehand Details.  The idea is to fill a page (or screen, if  you’re drawing with a graphics program like Photoshop and Sketchbook) with random, uneven shapes, and filling in the details of the nose, eyes, mouth, and so on.
Named for the knobbly, protruding, and random shape of your everyday, garden variety potato, The Potato Game is a creative exercise that allows you to break loose from the step-by-step structure of  drawing from a Simple Shape or Complex Shapes, with the creative anarchy of drawing from Freehand Details.

I’ll be revisiting these ideas in greater detail, with examples of how I approach each method  step by step.  In the meantime, I invite you to comment below, and stay tuned for more drawing tips.