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In the middle of a spring 2019 course entitled “Gender and Sexuality in the Ancient World,” after a suggestion by Jason Nethercut on Twitter, I assigned as readings a fundamental work on Roman sexuality by Holt Parker entitled “The Teratogenic Grid” (1997) and an Eidolon article by Sarah Scullin entitled “Making a Monster” (2016), which examines reactions to and consequences of Holt Parker’s arrest for collecting and disseminating child pornography. In response to these readings, students brought in modern examples of “popular art, problematic artist” like R. Kelly, Michael Jackson, and Cardi B. Using these examples, I then asked them to analyze the idea of the problematic creator for the ancient world. The romantic prescriptions contained in Ovid’s Ars Amatoria, for example, are problematic from the standpoint of content, but does that reflect misogynistic beliefs truly held by Ovid himself? Juxtaposing these modern and ancient readings opened up new avenues of discussion for the class, including the cultural and historical contingencies of legality and morality (a lesson already in progress through the discussion of gendered and sexual institutions in Greece/Athens like pederasty and marriage) and what we should (or should not) do about scholarly and artistic works produced by problematic creators.