This essay is an attempt to explore Basho Matsuo’s establishment of haiku as a significant moment in the history of Japanese literature where the perception of nature was drastically changed. It is often assumed that Basho’s poetry exemplifies aesthetic harmony between human beings and nature. However, with the help of recent critical discussions on the idea of nature I will argue that Basho’s poems entail intriguing paradoxes between, for example, the natural and the artificial, or between the legacy of the past and the perception of the present. A reconsideration of the literary, religious and social dimensions of Basho’s work will help us clarify how the poet, having mastered a range of styles, whether classical or contemporary urban, exposed himself to nature during his journeys in order to establish a new structure of aesthetics. I will draw on the “post-pastoral” debate to position Basho’s achievement among the great traditions that have expanded the possibility of representation by striking a subtle balance between uncritical acceptance and wholesale rejection of literary tradition.