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This essay examines anti-heroic images in American art. These images, which appropriate and even subvert the heroic, are grouped around four political protest movements that emerged during the 1960s: the civil rights movement, feminism, the environmental movement, and opposition to the Vietnam War. With the exception of the last, all of these struggles continue in some form today. Some of the artists discussed here refer in a given image to more than one protest movement, and art works focused on two different movements may share the same heroic referent. This essay considers “high” art by historic American artists from Emmanuel Leutze and John Singleton Copley to contemporaries such as Edward Kienholz and Kehinde Wiley, as well as imagery from popular culture such as the television series, The Simpsons. We see the joke of naming a cartoon character, Homer Simpson, after the author of the ancient Greek epic poem, the Odyssey. In the wake of the revolutionary movements of the 1960s, many people rejected traditional values along with heroic archetypes like the cowboy and other larger than life male stereotypes. The continuing popularity of the antihero in contemporary visual art parallels similar images in modern literature and in popular culture. Old definitions of the heroic got into question along with all authority figures. It may be that what we are witnessing is a shift in the popular mind from old notions of the heroic to a new popular imagination that now validates characteristics that were once thought to be un-heroic.