Morphology is one of the oldest branches of science, encompassing the form, structure, and transformation of natural materials, whether biotic or abiotic. In the context of contemporary Biology, morphology may be most broadly conceived as the qualitative and quantitative theory of extant and extinct phenotypes, themselves directly sampled via manual, molecular, or digital anatomy. This dissertation includes three evolutionary and systematic studies arranged from broadest to narrowest taxonomic scope. Chapter I presents a new general theory for the origin and evolution of male insect genitalia, drawing on skeletomuscular, developmental, and phylogenetic evidence across the Ecdysozoa. The main conclusions drawn from this study are that male insect genitals are composite organs which are homologous with abdominal appendages IX and X, and which have undergone various functional and developmental specializations corresponding to major ecological and life history innovations. This transformational pattern is also observed in Chapter II, which introduces a new family of stem ants, providing unique insight into the paleoecology and evolution of the Formicidae. With my coauthors, we employed Bayesian and maximum likelihood methods to solve the phylogeny of the total Aculeata, and to statistically estimate a time-calibrated transformation sequence crownward into the extant ants using traditional and digital anatomical data. Chapter III provides the first male-based key to and diagnoses of the ant subfamilies of the globe, and outlines a list of morphological characters and questions which seeded chapter II. The appendix to chapter III is an unpublished, male-based key to the ant genera of the New World. I conclude this dissertation with a taxonomic index of the higher classification of Aculeata and Formicoidea, as here conceived. Although the future of morphology will be digital, there is no replacement for the manual work of specimen collection, curation, and manipulation. Ultimately, bioinformatics will combine phenomics and genomics to model the continuum of developmental and phylogenetic anagenesis, constrained by functional dynamics. Pursuit of this vision will manifest a new era of biological research and education.