Phylogeny-based studies of fossil organisms are increasingly utilized in the field of paleobiology to address macroevolutionary questions while taking into account the shared evolutionary history of closely related taxa. Broadly, this dissertation is concerned with tree-based investigations of evolutionary patterns in the fossil record, with a particular focus on the evolutionary history of crinoids. Using the fossil record of camerate crinoids as a model group, chapters herein integrate alpha taxonomy, phylogenetic inference, systematic revision, and phylogenetic comparative methods to investigate diverse macroevolutionary questions. In addition to inferring new phylogenetic trees, this comprehensive approach serves both to improve the primary data used to infer phylogenies (i.e., alpha taxonomy, morphology, and taxon sampling) and to incorporate phylogenetic hypotheses into tree-based studies of evolution in the fossil record. Descriptions of crinoid faunas from the Upper Ordovician (Katian) of Ontario and Spain were conducted to improve the resolution of paleobiogeographic and stratigraphic sampling in morphological datasets, and newly described taxa were included in subsequent phylogenetic analyses. Evolutionary relationships among camerate crinoids were inferred, and the resulting phylogenies were used to inform systematic revisions of crinoid classification. In addition, recovered trees were integrated with high-resolution morphologic and ecomorphologic datasets to conduct phylogeny-based studies of morphologic evolution and extinction selectivity, focusing on the role of ecology in the generation and maintenance of these patterns.