Louis Wirth's 1928 book The Ghetto may be the most important work of interwar American sociology focused on Jewish life. Although The Ghetto has received some attention from scholars since its publication more than 85 years ago, very few observers have paid any sustained attention to that fact that the book includes six striking woodcuts by the "dean of Chicago Jewish artists," Todros Geller. This essay treats Geller's woodcuts as more than mere illustration, putting them in conversation with Wirth's text in order to examine how these two Chicagoans wrestled with the modern American Jewish dilemma of living between two worlds, and not being fully at home in either. Both Wirth and Geller sought to address a path forward for Jews, even if they did so in very different media. Their interests, and their personal histories, shared many commonalities. Their works, in this single important volume, embody the anxieties at the heart of American Jewish intellectuals' concerns about modernity.