I have been out this week and am behind on the concept development & feedback.
My project is comedian Louis C.K. at The MGM Grand in Las Vegas. Louis has some NYC dates, but he lives there and always performs there, so I thought the glitz/gambling of an upcoming Las Vegas show would be an interesting setting. I am a graphic designer and not an illustrator so much, so I wanted to keep the style bold & graphic.
I wanted to juxtapose Louie's head into gambling somehow... I thought about having Louie's bald head be the ball in a roulette wheel, but decided that to include enough of the wheel to make it recognizable would make his head proportion too small. So I went with my next idea, sort of a blackjack look with a green background (like the felt on the table), and 2 cards showing. The top one would be a joker, with Louie's head in place of the traditional jester/joker image. (the bottom card would be either a King or Ace-- ultimately I chose King since Louis is one of the kings of comedy right now. The joker usually has a colorful "bib", but Louis always wears black, so I went with that.