This article examines how the critically acclaimed television show Mad Men (2007-2015) sells romanticized working-class representations to middle-class audiences, including contemporary cable subscribers. The television drama’s lead protagonist, Don Draper, exhibits class performatively in his assumed identity as a Madison Avenue ad executive, which is in constant conflict with his hobo-driven born identity of Dick Whitman. To fully examine Draper/Whitman’s cross-class tensions, I draw on the American literary form of the hobo narrative, which issues agency to the hobo figure but overlooks the material conditions of homelessness. I argue that the hobo narrative becomes a predominant but overlooked aspect of Mad Men’s period presentation, specifically one that is used as a technique for self-making and self-marketing white masculinity in twenty-first century U.S. cultural productions.