Viviparity (live birth) represents a significant evolutionary innovation that has emerged in hundreds of lineages of invertebrate and vertebrate animals. The evolution of this trait from the ancestral state of egg laying has involved complex morphological, behavioral, physiological, and genetic changes, which enable internal development of embryos within the female reproductive tract. Comparable changes have also occurred in oviparous, brooding species that carry developing embryos in locations other than the female reproductive tract. This review explores the taxonomic distribution of vertebrate viviparity and brooding (collectively termed pregnancy), discusses the adaptations associated with internal incubation, and examines hypotheses surrounding the evolution of pregnancy in different lineages. Understanding the mechanisms that have led to the emergence of this trait can illuminate questions about the evolution of reproductive complexity and the processes that led to the emergence of evolutionary innovations that have shaped the remarkable diversity of Earth's fauna.