Rabbi Ila'i said: “If a person senses themselves overpowered by their urges, they should go to a city where they are not known, dress in black clothes, cover their head in black, and do what their heart desires, but let them not desecrate God’s name in public” (B. Talmud Moed Katan 17a). With reference to artists and writers from Michelangelo and Bernini to Bakhtin and Bataille, we will explore the religious struggle with transgression through the lens of several Talmudic texts.