This paper begins by juxtaposing contemporary discourses on Harlem and the Lower East Side, arguing that the processes of iconization of these two neighborhoods have been very different. Whereas the iconicity of Harlem has always been shot through with ambivalence, the Lower East Side has come to signify a relatively unambivalent sacred space for US Jewry. The second part of the essay then traces the representations of Harlem and the Lower East Side back to early twentieth-century African American and Jewish American novels, claiming that critically analyzing the theme of ambivalence in these texts – and, more specifically, how ambivalence manifests itself differently within each literary tradition – is key to understanding not only why Harlem and the Lower East Side have undergone parallel but divergent processes of iconization, but also the way Jews and blacks have been positioned and have attempted to position themselves in relation to dominant white US society.