Okay we've only just begun to tap into the possibilities here. How about some Advice Dog-style pics? Overlay text at the top at bottom here, it doesn't have to be funny, it can be profound or sad as well. Whatever his face makes you think he would say, what kind of guy he is, how he feels about life:
I'm in the middle of designing a highly exclusive range of T-Shirts, which will be worn at all this season's most exclusive Cannes pool parties. Here are my designs, what do you think?