In 1962, Norman Rockwell's illustration The Connoisseur appeared on the cover of the Saturday Evening Post. Featuring a middle aged man in a grey flannel suit, staring at a Pollock-esque drip painting with his back turned to the viewer, the piece was a direct rebuttal to Clement Greenberg and critics like him. Such critics had long maligned the illustrator, and commercial artists in general; deeming them nefarious confectioners rotting the teeth of audiences worldwide. The Connoisseur is a rare example of a commercial artist entering a debate which shame, insecurity, and artistic hierarchy had previously excluded him from. As Rockwell here embodies the role of critic, he inverts the traditional dynamic and provides a fresh perspective on the mid-twentieth-century debate between "high" and "low" art. This paper looks at this debate and its various participants through the the lens of this very unique Rockwell cover.