As generic and higher-scale evolutionary relationships are increasingly well understood, systematists move research in two directions: 1) understanding specieslevel relationships with dense taxon sampling, and 2) evaluating evolutionary patterns using phylogeny. In this study I address both foci of systematic research using pitvipers, subfamily Crotalinae. For direction one, I evaluate the relationships of 96% of pitvipers by combining independent sets of molecular and phenotypic data. I find the inclusion of species with low numbers of informative characters (i.e. less than 100) negatively impacts resolution of the phylogeny, and the addition of independent datasets has no effect on or a small benefit to confidence in estimated evolutionary relationships. Combined evidence is extremely useful in evaluating taxonomy; I use it with South American bothropoid pitvipers. Previous work found the genus Bothrops paraphyletic, but no study had included enough species to propose a taxonomic resolution. I resolve the relationships of 90% of bothropoid pitvipers, and support the paraphyly of Bothrops as previously defined, but find it consists of three well-supported clades distinguished by distinct habitats and geographic ranges. I propose the division of Bothrops sensu lato into three genera. To address research direction two, I investigate the change in reproductive mode from egg-laying (oviparity) to livebearing (viviparity) in vipers, as well as the expansion of pitvipers through South America. I resolve the phylogeny and the divergence times for subgroups of interest then use model comparison and ancestral character state or iv geographic range estimation to trace the evolution of reproductive mode or geographic range across evolutionary history. For vertebrates, the predominant explanation for the evolution of reproductive mode is Dollo’s Law of unidirectional evolution. This law has been challenged for a number of characters in different systems, but the phylogenetic methods that found those violations were criticized. I find support for unidirectional evolution in two analyses and rejection of it in others, and therefore do not reject Dollo’s Law for the evolution of reproductive mode in vipers. In the case of geographic range, dozens of hypotheses have been proposed to explain the great biodiversity in South America, but tests of these hypotheses are lacking. I define specific time- and space-based predictions for seven hypotheses based on geological and climatic events – uplift of the Andes Mountains, saltwater inundation of inland areas, change in river flow, and Pleistocene climate changes. I find some support for half of the hypotheses, including one allopatric, one parapatric, and one based on climate change. I conclude that the evolution of South American pitvipers is extremely complex. Through fulfillment of both systematic research directions, I generated new knowledge about pitvipers and evolutionary processes. My methods of evaluating evolutionary patterns provide frameworks for different research questions in these areas, and I suggest that other researchers apply similar techniques to evaluate other portions of the Tree of Life