In 1960s Rio de Janeiro, the Brazilian white middle class embraced the samba music written by working-class blacks as a source of authentic national culture. Cultural mediators, or individuals that bridged sociocultural spheres and negotiated the terms in which work was produced and circulated, were essential to samba’s mainstream acceptance. This article examines how the Rio de Janeiro bar and restaurant Zicartola functioned as an alternative space of encounter during a period of social and political upheaval. Following the trajectories of musicians Nara Leão, Paulinho da Viola, and Clementina de Jesus, the article traces Zicartola’s position as conduit for the exchange that occurred between the middle and working classes between 1963 and 1965. Although cultural mediation is often framed as a way to bridge differences between disparate communities founded on differences in race and social class, these interactions only cause transformations on an individual scale while reaffirming the imbalance of power through the unequal distribution of social and cultural resources.