Whew! Well here's my first entry. I contemplated doing this digitally but I've had so much fun with my Copic markers recently that I decided to just do the entire thing traditionally.
Also, I wanted to modernize him as suggested but didn't want to overdo it with too many elements so I decided that the lone smiley face- a popular icon from the 70's- would be the perfect fit to counteract the moody demeanor of the piece (Plus, it's funny!)
I still might send another entry in with a dash more color but I also really like the contrast between the drab grey tones and the bright yellow of the 70's Smiley Face button.