Marshall Berman was an optimistic and provocative writer on cities and urban life. The article begins by examining examples of Marshall Berman’s unique approach to understanding the potential of cities to help people discover themselves and each other, including his analysis of Alfred Eistenstaedt’s photograph of the VJ Day kiss in Times Square (included in his final book On the Town). Berman’s unique contribution to understanding urban culture, made across many books and articles, is shown to combine a humanist, or ‘warm stream’ reading of Marx, with Nietzsche’s enthusiasm for affirmation. The article argues how Berman’s work stresses remaining faithful to the city despite the challenges, hardship and complexities of urban life. For Berman, it is only the city that can help resolve the modern quest for authenticity and radical individualism. Finally, the article considers two critical issues that arise from Marshall Berman’s work: first, the problems of social and moral order that might arise from unbounded development of the self; and second, whether it is possible to construct a radical politics of affirmation—as Berman tries to do—and if so, why we might need it now more than ever.