In this article, based on two case studies conducted in Stockholm and London, we discuss how graffiti and street art provide forms of expressive cosmopolitanism in reclaiming voice and reciprocity in the city. Through in-depth interviews and observations, we explore how urban artists, using their practice, foster ever-transient and contesting senses of outsidered aesthetics and communicative culture that both seek to challenge the institutionalization and hegemonic indoctrination of today's media cities and, as such, become part of the ensemble that constitute its visual geography. While there are many parallels and inter-urban synchronicity, our results indicate that locally-specific elements are prominent in each city. Both studies indicate that the solidaritarian and spatially mediating character of graffiti and street art, and not just their contents, constitutes a resource in sustaining the possibility of coproducing worldly visions in and of the cities. They both observe struggles for openness and social critique taking place across time and space.