This thesis positions realist painting as a site of visual innovation and critical reflection in a cultural climate dominated by advanced representational technologies. Focusing in particular on the work of Eric Fischl and Will Cotton, I examine how these contemporary realist painters establish a dialogue with current visual technologies. I also posit and explore these artists’ inheritance of a set of concerns from the American Photorealist painters of the 60s and 70s— a group of artists who I suggest have been misconstrued as the regressive anomaly during an otherwise avant-garde art historical moment. Through an extended consideration of the questions and visual strategies shared by Cotton, Fischl, and the American Photorealists, I demonstrate how their respective visions of “realism” reflect a critical awareness of the technological and socio-cultural changes unique to their respective historical moments.