Challenging perspectives on the urban question have arisen in recent years from beyond academic realms through the work of artists and cultural practitioners. Often in dialogue with urban theory and political activism, and employing a range of tactical practices, they have engaged critically with cities and with the spatialities of everyday urban life. They are typically concerned less with representing political issues than with intervening in urban spaces so as to question, refunction and contest prevailing norms and ideologies, and to create new meanings, experiences, understandings, relationships and situations. Such interventionist practices may rarely be seen as part of the traditional purview of urban studies. Yet in asserting their significance here, this essay argues that growing dialogues across and between urban and spatial theory, and artistic and cultural practice, have considerable potential for inspiring and developing critical approaches to cities. The essay highlights a number of specific challenges thrown up by such interconnections that are of political and pedagogical significance and in need of further debate.