This paper argues in favor of a practice of queer optimism, joy, and revelry in the face of ongoing grief and violence. I assert that the work of Puerto Rican artist/performer Villana Santiago Pacheco (“Villano Antillano”) operates as a polyvalent expressive practice that transgresses the sonic, visual, and social traditions of the Urban Puerto Rican musical scene through campiness, friction, and blatant sexuality. I examine how she explores ideas of perception and identity by teasing, questioning, and undoing the linguistic and visual semiotic imaginaries that exist in Puerto Rican society regarding trans women/folks, while also pointing to the different registers of labor that she and, more broadly, trans women perform (including, but not limited to, sex work). Villano ultimately shows us new ways of creating and maintaining sociality, of paving forward through the dancefloor, through the street, through the conditions that seek to keep us dispossessed.