This chapter offers a cursory excursion into philosophizing about international law. This historical journey reveals how the interest in law beyond the state (polis) was born with the natural law doctrine and its idea that certain legal rules are of universal validity. This philosophical doctrine has been playing throughout the centuries a dominant role in formulating theoretical background for the study of international law. However, this philosophical landscape has slowly started to change with the rise of the 19th century legal positivism. While it became the dominant force in the German international legal discourse (Staatswillenspositivismus), the British school of analytical jurisprudence “found no room for a law beyond sovereignty.” The subsequent influence of the analytical school of thought was reflected in the fact that most of jurisprudential dealings with international law, including Hart’s, did not go far beyond the ‘ontological’ question of whether international law is ‘true’ law, thereby reinforcing skepticism of the pioneers, Bentham and Austin.