Thanks for the designs. Unfortunately the caricatures are a bit too complicated. We are thinking along the lines of something that can be screen printed on t-shirts (can't have shading and gradients). Also, for legal reasons, we are trying to stay away from using caricatures of other famous people. If you can make it so that Frank is doing the faces of each caricature, it would be better.
Here is a photo to reference:
http://www.frankcaliendo.com/dl/promo/logotournament/Frank-AllOverThePlaceDvdCover.jpg