The cool kids of the art world always laughed at Norman Rockwell because he was so square and representational. He kept painting that way and presumably cried all the way to the bank, but he also did something else. With The Connoisseur he did to abstract expressionism what postmodernists always want to do to their predecessors. (Something I learned only recently: Rockwell always worked from models, so in order to do this painting he first did his own Jack the Dripper “painting” and copied it.)
Sam Spratt has painted nine pictures of African-Americans in the style of the master. This is not an expert opinion, but I think he is a worthy successor.