The TV show Mad Men (2007 – present)1 explores the world of postwar working-class America through the eyes of Donald Draper (Jon Hamm), a copywriter from Madison Avenue, New York. Draper’s job in the booming 1960s advertising industry provides a look into the social history of twentieth century America that deconstructs representations of the times as a period of stability and easy social advancement. Through a reworking of postwar Hollywood aesthetics, Mad Men focuses on Draper’s difficulties in concealing his working-class origins and negotiating a middle-class personality. His enterprising, yet conflicted identity, dwelling in between two worlds, embodies the contradictions that afflicted a generation of “mental” salaried laborers and the crisis of class-consciousness that accompanied the postwar bourgeoisification of the American. Draper’s struggle to retain integrity in the face of instability reveals how Mad Men’s representation of work is tied to the work of representation of a drifting and unstable self.