Singapore faces a crossroads. Decades of top-down arts policies have given rise to a robust grassroots arts community, yet this cultural shift has also exposed tensions and contradictions. Indeed, Singapore’s ‘cultural turn’ has unleashed forces and tensions that may be uncontrollable, and may be shifting the City-State in new and uncharted directions. In the context of growing activism around the world, Singaporean ‘artivists’ seek alternative forms of place-making and creative expression, sometimes reifying, at other times challenging, the State and the status quo. Yet this artistic-activist community is far from being a united front. The State, likewise, is not a single, coherent entity, but is fluid and shifting, sometimes allied with, at other times opposed to, art-led activism. Space is a crucial lens in which to explore these tensions and contradictions. The findings of this thesis are summarised through a three-pronged taxonomy of cultural-activist spaces: indoor space, subdivided into theatres, galleries, cafés, and the spaces of the university; outdoor spaces, which range from State-designated spaces of activism to ‘pop up’ spaces of arts-led activism; and, finally, digital space, which spans social networks and the Singaporean ‘blogosphere’. Each spatial scale contains distinct possibilities and limitations on the effectiveness of, and the ability for, such activism to be transformative and influence policy shifts. These spaces are, of course, also often blurred. This thesis adds to the emerging conceptualisation about ‘cultural activism’, particularly in the context of the non-Western world, and thus broadens the ‘worlding’ of urban theory. Questions are raised about assumptions around concepts such as authoritarianism and the arts, which, in Singapore, are revealed to be complex and highly fluid. This thesis can also inform policy-makers in terms of practical application, as the decades of arts and culture policy in Singapore can now be understood to have produced a multitude of tangible, measureable results (some of which were intended, while others were not).