Today, artists play a key role in the development of post-industrial cities. Through the highlighting of the ‘creative class’, the emphasis on ‘the creative entrepreneurial self’ or the increasing co-option of artistic criticism in late capitalism, creativity, art and culture is gaining more influence in the development of cities. However, artistic interventions in urban space are not primarily concerned with concrete political issues but with intervening in urban spaces in ways which “question, refunction and contest prevailing norms and ideologies” (Pinder 2008). Critical artistic interventions can be seen as a step out of the realm of an autonomous art and out of protected exhibition spaces as a “strategy [to] draw attention to existing (social, political, institutional, urbanistic) structures and to reshape them” (Wege 2001). We examine the ways in which artists are politically active in the city, combining aesthetic aspects and political protest in different ways and intensities. In our empirical study, we have compared four German and Israeli cities, Hamburg, Hanover, Tel Aviv, and Jerusalem, and found several types of critical artistic interventions. We posit that specific social, cultural and political circumstances in these cities, their ‘spirit’ (Bell/de Shalit 2011) or ‘intrinsic logic’ (Löw 2011), influence the mode and the intensity of this artistic activism. For instance, we claim that a certain policy by the city (for example neo-liberal policies oriented towards economic profit) is a cause for the critical rebelliousness or reticence of artists in their city. Relying on extensive qualitative interviews and group discussions and systematic content analysis, we show how the strategies and attitudes of artists/ artistic collectives are influenced by this specific ‘spirit’ or ‘intrinsic logic’ of a city, which affects special forms of critical actions. To illustrate this reciprocal relationship, we will present a categorization of different forms of interventions, which range from smaller interventions that interrupt the everyday practice to the creation of alternative ‘urban spaces of possibility’ or critical interventions of outspoken opposition and protest.