Recent research suggests we cannot understand how people make sense of state-led nationalism without considering how people interpret nationalist values through interactions in, and representations of, local environments. Indeed, Istanbul’s changing urban environment played a role in local interpretations and critiques of the state nationalist project in the Republican era. Satirical journals of the 1930s and 1940s printed humorous cartoons and essays about a diversity of topics, from Turkish foreign policy to Istanbul’s changing urban landscape. They occupied a critical stance with regard to state propaganda, in part because of Istanbul’s position of alterity with regard to Ankara, the location of state power. This paper examines texts and images from the journal Akbaba as representations that contributed to the production of a distinctly Istanbulite urbanism, a particular urbanism that developed within the larger nationalist context. Images of urbanism portrayed Istanbul as a distinct locality, with particular landscapes, such as streetscapes in the modern urban center of Taksim, or houses of non-Muslim minorities on the island of Büyükada. These images also communicated changing cultural notions of who belonged/did not belong in Istanbul’s places (with drawings of men in modern hats and overcoats in Taksim, wealthy non-Muslim minority women riding ferries to Büyükada, or a headscarved rural migrant woman looking incongruous on a modern boulevard because she is riding in an automobile). Images and texts about urban life created particular meanings of whose bodies, dress, and behaviors were modern and urban; as changing social norms found validation in an Istanbulite urban image, these ideas reverberated alongside the values of Turkish nationalism circulating at the time. The cartoons and essays, however, betrayed a deep skepticism regarding the Turkish nationalist project by lampooning state and municipal efforts to control the city’s social complexity. Cartoonists drew humorous images of wealthy, modern districts contrasting with ugly urban poverty; modern urban planning projects failing to transform Ottoman landscapes; and anti-Semitic cartoons next to funny essays about the new habits of modern life. Nationalist issues of ethnicity, modernity, and secularism collide, on the page, with the themes of class, urban development, and demographic change, just as diverse people interacted in urban places and inhabited Istanbul’s distinct landscapes. This paper argues for considering the impact of urban phenomena on emerging notions of Turkish cultural, national identity in the Republican era, and views images of the city, in turn, as dialectically produced within the nationalist context.