This article examines self-disparaging representations of “the German man” in humorous middle-class visual and textual publications of the 1840s. Considering contemporary notions of German national character and the emergence of contradictory masculine ideals, the analysis traces the dual representation of the German man as either an emasculated philistine or a hypermasculine quixotic hero. Based on this analysis, it argues that just as a German national movement was acquiring unprecedented political potency, a highly gendered sense of German national ineptness was widespread among the German bourgeoisie. Both the philistine and the quixotic German were cast as inadequate in the face of a corruptive, feminized modernity that was unfairly advantageous to the French. These findings underscore how gender and national stereotypes in nineteenth-century Germany were mutually destabilizing and repeatedly negotiated, profoundly shaping contemporaries’ understanding of the world changing around them.