This article addresses the activation of aesthetics through the examination of an acute sensitivity to melancholy and time permeating the literary and pictorial arts of Japan. In medieval court circles, this sensitivity was activated through a pervasive sense of aware, a poignant reflection on the pathos of things. This sensibility became the motivating force for court verse, and through this medium, for the mature projects of the ukiyo-e ‘floating world picture’ artist Katsushika Hokusai. Hokusai reached back to aware sensibilities, subjects and conventions in celebrations of the poetic that sustained cultural memories resonating classical lyric and pastoral themes. This paper examines how this elegiac sensibility activated Hokusai’s preoccupations with poetic allusion in his late representations of scholar-poets and the unfinished series of Hyakunin isshu uba-ga etoki, ‘One hundred poems, by one hundred poets, explained by the nurse’. It examines four works to explain how their synthesis of the visual and poetic could sustain aware themes and tropes over time to maintain a distinctive sense of this aesthetic sensibility in Japan.