The existence of ancient deep-water lakes provides an opportunity to study the independent adaptation of aquatic organisms to pelagic, benthic, and rocky shore habitats. With improving resolution of their phylogenetic relationships, the many cichlid fish species endemic to the African Great Lakes Malawi, Tanganyika, and Victoria provide a significant resource for the comparative study of such evolutionary processes. Here, we show that cichlid lineages colonizing rocky shores and pelagic habitats in the different lakes have independently evolved larger eggs and lower fecundities than benthic lineages, suggesting parallel adaptive life-history evolution. By contrast, other pelagic teleost fishes in both marine and freshwater habitats, including African lakes, typically produce large numbers of very small eggs. Our results also suggest that decreased fecundity and increased egg size not only occurred independently in each lake but occurred independently in the colonization of rocky and pelagic habitats.