This article provides a close and practice-led investigation into the complexities and complicities of politicised collaborative art within an era of neoliberal urbanism. In addressing these complicities from a practice-led perspective, the paper provides a nuanced account of the social functions of art based on critical perspectives relating to issues of urban politics as well as politics of collaboration, participation and representation. Reflecting on experiences with facilitating socially engaged artistic projects in Basel, Monthey and London, I demonstrate the challenges faced when struggling to adhere to the artistic aims of providing transformative experiences, while at the same time working within various neoliberal and institutional constraints and expectations. Rather than succumbing into totalising narratives about how art practices are inevitably instrumentalised as they become part of neoliberal structures, logics and ambitions, the paper emphasises the need to think more carefully about the politics of this practice in terms of how it constantly negotiates and reflects the subtle power relations that exist between artists and their collaborators in urban contexts.