Located in the theoretical triangle of urban, cultural, and political studies, this paper examines artists’ political engagement in cities. Applying a qualitative approach through inter-urban fieldwork in Hamburg and Hanover, Germany, and Jerusalem and Tel Aviv-Jaffa, Israel, we study how artists critically engage with their cities and urban spaces, and analyze how the artists’ themselves perceive and practice their own actions. Based on this, we offer a typology of artists’ attitudes and behavior patterns toward urban politics and policies, which we propose as a relevant theoretical tool for analyzing political engagement of artists in the urban environment.