Two weeks ago I had to do a pretty quick turn-around job for Bryn Mawr College. The illustration was to be of 6 different crew boats with 30 people distributed between them. Since I didn't have the time to draw each individual, I drew 3 instead: one coxswain and one female and one male rower, plus the back and front of the boat. I then drew many different heads of different races (as shown below) and stuck them on the bodies.
I wish I had the time to vary the strokes each team was taking, but sometimes you just have to get the job done. I still think it turned out pretty nice.