An important problem for high school art teachers is deciding what belongs in the art curriculum. What works of art, media, or ideas will inspire their students to more fully develop their own artistic potential and critically engage with contemporary art and culture? What artifacts of art, visual culture, or material culture should be included and how can these artifacts be connected to student interests? This article will visit these questions and contextualize figure drawing within contemporary art practice and emerging discussions about art education curricula. Although new media and technologies have important and unexpected places within the art curriculum, traditional forms of artistic expression can also provide significant artistic experiences if they are given meaning within contemporary art, culture, and the lives of students (Gude, 2004). Woven into this description of figure drawing are ideas about how curriculum structure and a hospitable environment can nurture generative conversations among teachers and students. (Contains 4 figures.)