In what follows, I will examine two such strains of dominant contemporary legal thought: American Legal Realism, as exemplified by the work of two prominent jurists, Oliver Wendell Holmes, Jr. and Benjamin Cardozo, and the legal positivism of British philosopher H.L.A. Hart. In doing so, I will attempt to show how both projects evidence a dissatisfaction with the much of the history of legal philosophy, rejecting the metaphysical and austere academic tendencies of prior schools of jurisprudence in favor of an emphasis on practice and social reality. Crucially, however, I will argue that while Hart’s understanding of legal positivism in The Concept of Law has commonly been understood as dealing legal realism a fatal criticism (that, in failing to focus on the ‘internal point of view,’ it fails to provide a convincing answer as to the question of the nature of law), there is still much of value in the legal realist project. Even if one accepts Hart’s criticism of Holmes’ prediction theory of law, as Hart understands, there remains in both Holmes’ and Cardozo’s work a commitment to understanding the process of judicial adjudication that stands as a novel and significant contribution to jurisprudential discourse.