This article revisits the complex intersections of identity and meaning in the context of a world in which cosmopolitanism is increasingly questioned. The role of the artist with regard to activism and cosmopolitan flows becomes difficult to navigate but important to probe. Findings drawn from fieldwork indicate that the artist is highly conflicted; often ephemerally aligned with various social movements that may or may not be related; and in a constant state of self‐negotiation and identity formation that are highly dependent on local context. Intersectionality may be a useful frame to reconceptualize the artist as a relationally connected set of constantly shifting identities rather than an assumed category, as sometimes portrayed. Key to this is an appreciation of the role of the observer in this process. Singapore is envisioned as a place of intersecting identity; so, too, are the artists within it, caught between local context and global currents.