Singapore is at a critical juncture. Riots in 2013 brought simmering cultural, class and ethnic tensions to the surface: Lee Kuan Yew's death in March 2015 has caused the nation to pause and reflect on its past and future. A cultural war has seen progressive and conservative societal factions battling over ideological and material space. Parallels can be drawn to resurgent activism witnessed around the world, from ‘Occupy’ and the ‘Arab Spring’ to current movements in Asian cities. Authors have been revisiting and reconceptualizing urban social and political movements, with ‘cultural activism’ and ‘creative resistance’ gaining traction in literature. Increasingly, such literature is expanding to include non-Western cities and differing political contexts. However, Singapore's unique context invites (and requires) a closer reading of what the ‘new’ geographies of activism look like in a quasi-authoritarian context, and the make-up and characteristics of activist coalitions and alliances deserve a revisiting in such a setting. This paper uses empirical examples from Singapore to show that urban social movements (USMs) may not be as easily demarcated or identifiable as they are sometimes represented. ‘Right’ and ‘left’, ‘State’ and ‘society’, and ‘activist’ and ‘non-activist’ overlap and interact in complex ways unique to Singapore's ‘illiberal pragmatic’ structure. Therefore, this paper addresses the transferability of ‘cultural activism’ conceptualizations to less-democratic settings or city-state scales, presenting the activist spaces as somewhat ambivalent and ambiguous, within a wider cultural war. Findings are presented through the cases of Bukit Brown and Singapore's ‘digital sphere’, illustrating where possibilities and impossibilities for ‘spaces of hope’ might be found, and exploring the tensions intrinsic to Singapore's cultural landscape.