High Plains Drifter

My most recent painting is a portrait of David Kennedy, a dear friend of my parents' who has done some amazing work with inner city gangs. His approach to gang violence and gun control had an amazing effect in Boston during the 90s, and he's been coordinating similar programs in other cities. He was recently profiled in the New Yorker, and to honor this prestigious event, my parents commissioned a portrait of him embodying one of the phrases used in the article, describing him as a "high plains drifter." This is quite apt; David looks like Jesus dressed like John Cusack in "Grosse Point Blank." 
I like how this painting turned out, but I fear it can't rival the illustration of David in the New Yorker. Once you've got that, you know you've made it!