I drew a series of 10 silhouettes. It's a good exercise that pushes you to explore various shapes and attitudes.
As there is no details other than the ones that stick out at the periphery, I had to think about accessories that would agive a clue about the character.
This exercise is used by concept artists to generate a large number of variations within a short time.
For my own attempt, I drew with a Faber-Castell PITT brush pen, which is pointy enough for details but has a long tip that makes blocking-in the shape easy.
I spent no more than three or four minutes for each charater.
Silhouette drawing is not only for cartoonesque characters. A first application in "serious" art is to paint figures in the light.
Claude Joseph Vernet - Seaport by Moonlight [Source: Wikimedia]
A silhouette well placed can bring drama or mistery to a painting. The more striking example I can think of is the silhouette that Velázquez placed in the door frame for his painting Las Meninas.
Las Meninas, by Diego Velázquez [Source: Wikimedia ]
I you want to avoid boredom in your painting, then all figures should result in a different silhouette. Let me take the example of the painting Bonjour Monsieur Courbet, by the French painter Gustave Courbet, to illustrate the point.
Gustave Courbet - The Meeting or Bonjour Monsieur Courbet [Source: Wikimedia]
After I blackened each figure, the characters are all distinct. You could even guess, from the silhouette alone, the mood of each of these character. Courbet, on the right, holds his head high. With his long walking stick, he seems very stable and looks statuesque. The gentleman in the middle is welcoming with his arms open. As for the third gentleman on the left, he respectfully bow his head and looks humble.