The picaresque genre attempts to represent a subject outside History—in early modern Europe, the newly dispossessed peasant, “dissolute, crooked, thieving and idle”—who will eventually become the modern wage laborer. The genre uses slapstick humor and parody to make for witty stories that to this day retain their power to make us laugh out loud. But alongside the genre’s humor, the picaresque also figures its protagonists’ refusal to submit to the discipline of wage labor. Attending to the ideological and aesthetic strategies of the picaresque, this project examines the ways in which the genre has acted as an apparatus of capture for those living outside and on the margins of the enclosures of wage labor and the home. At the same time, it takes the picaresque as the genre of the lumpenproletariat and a chronicle of the making of new forms of life. The errant path of the rogue in the long picaresque traced here begins in early modern Spain, in La Celestina and Lazarillo de Tormes, moves through 18th C. England in Moll Flanders, leapfrogs continents and centuries to reappear in 1970s Mexico City in El vampiro de la colonia Roma, and ends with a bang in contemporary South Africa in Thirteen Cents. In terms of method, this project thinks alongside Herbert Marcuse, who writes that “art is perhaps the most visible ‘return of the repressed.’” It interrogates the shift in the literary figuration of the poor from holy mendicant to homeless subject, reading the genre slant—like a picaro—and against its function as moral fable of capital, in order to reveal a rich lumpen imaginary overflowing with other ways of being and living. Finally, in imagining a time before and after the long picaresque, I sketch out the contours of a radical psychoanalysis grounded in the urgency of working through the deadening effects of the philosophy of productiveness and the pain of private property.