You sometimes see a random silhouette like this in a antique store. Well I have 4 and these are of myself and my sibs. I vividly remember having these done by an art teacher in Marshfield, WI. We went to her house in the Summer and I think she used a projector and drew them. She needed to know our ages so she could arrange them correctly. Note the good composition. I am the first one and I look left and up. My brother looks right and down. And the two in the middle are looking at each other. I always liked these. Neither of my sisters wanted theirs so I have the whole set.
I am often asked how you would make these and I recently found this book Silhouette Art. I did not get the book so I cannot tell you for sure that you can make a silhouette of someone you know but I would think it would be a good starting point. It is very reasonably priced on Amazon. There is a link on the lower right if anyone is interested. Have fun!