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My paper takes as its premise that the Aristotelian construct of the “natural slave” (Pol. 1254b16–1255b15) was active in ancient Rome, and that it involved an ascription of difference so essentializing as to constitute an act of premodern racial formation (for the relevant definitions of race and racism, see Isaac 2004 and 2006; Haley 2009; Heng 2018; and esp. Murray 2021). I then trace within Roman comedy—a genre whose playwrights and performers included many who were of enslaved or freed status (Richlin 2017)—a sustained challenge to this racializing Aristotelian notion. I conduct a reading especially of the role reversals and acts of mutual impersonation between the free and the enslaved that define Plautus’s Captivi (cf. Moore 1998). The staging of the moments in question leaves little room for the idea that there are indeed some people who are naturally suited for enslavement and others who are not, or else the characters in question would not be mistaken for one another so easily. Next, I move on to an assessment of epidermal and other somatic factors (such as the ones so prevalent in modern racial categorizations) in Roman comedy’s undermining of racializing assignations of difference. Here, I argue that such plays as Plautus’s Poenulus and the corpus of the freedman Terence, himself apparently colore fusco (Suet. Vita Ter. 6), undermine noxious attitudes against those who are Othered in the dominant discourse because their enslaved status might be seen to align with their regional origin and/or the fact that their skin color was significantly darker or lighter than the somatic norm at Rome. Applying these observations to the genre as a whole, I conclude by considering the role that the servus callidus plays alongside comedy’s broader costuming and masking conventions in reinforcing the above points in other palliatae. The trickster as stand-in for the playwright/poet actively undermines the notion that the enslaved can only ever serve as tools of the free, and that literary authorship and other forms of agency are the exclusive domain of the enslavers. Race here emerges as a persona worn by, or forced onto, performers, a mask that defines their experience in significant ways but ultimately symbolizes a social construct that remains distinct from the human being that wears it.