Two prominent media events involving breastfeeding celebrities prompted unprecedented transnational media attention to their bodies, their breastfeeding practices, and their beliefs about the act of breastfeeding. This study critically analyzes media representations of Salma Hayek and Angelina Jolie that feature (or imply) a nursing celebrity breast to argue that discourses about celebrity breastfeeding are a semiotically potent phenomenon that destabilize boundaries of public and private, perpetuate normative beauty standards, and prescribe proper breastfeeding practices to audiences. The transnational celebrity of Jolie, Hayek, and others makes analyzing media discourses of their breastfeeding particularly necessary because they are prominent purveyors of femininity and have made activism about women's health a key aspect of their public personae.