Here are two more drawings I did for a family that will print them on T-Shirts... one on each side. Twenty people in all. Drawing this on computer makes this so much easier than it otherwise would be. I start by completing all the faces, then I arrange them on the layout according to what they will be doing on the picture. Some may be sitting thus making the head placement toward the bottom. Another couple might be engaged in some activity together, such as tennis, so I place them side to side. Once I've placed the heads, I start sketching a "pencil" of all the bodies, etc. Now I can shove things around to make them fit just right. I then set this page up as though there's a sheet of tracing paper over it and redraw the entire thing in ink. I color using the digital equivalent of watercolor and oil pastel. Drawing this way on computer gives me a huge advantage over traditional paper. I can experiment, make mistakes and always will have a way to back out and try again.
I often get requests do do group caricatures for greeting cards. This year was unbelievably busy with requests. I had a surge of calls in November that was great... but frustrating. I simply had to turn down so much work. Nice problem to have, I guess.