This chapter discusses Rego’s Virgin Mary works, which not only engage with aspects of the Marian cult, but also question some basic premises of Christian dogma. Lisboa argues that in these images, key doctrinal points are contravened by a series of compositional, symbolic, and casting devices, and she explores the effect of this contravention. Lisboa then examines the artist’s emphasis on the human condition of Mary and Jesus. Lisboa further explores the artistic tradition of religious imagery, both the difficulty it poses for artists, and Rego’s employment and exploration of it. Religious polarization and skepticism, such as the Epicurean Paradox, are considered. In the remaining sections of the chapter, Lisboa gives a full discussion of Rego’s focus on Mary in these works, and the questions that they invite.