Mono no aware is considered to be one of the central-most Japanese aesthetics and distinctive to Japanese identity (Keene 1995; Miller 2011). This aesthetic standpoint finds wistful beauty in the transient, and is most often translated to ‘beauty in pathos’ or ‘the ah-ness of things’ (Hume 1995), as exemplified in the Heian-era classic, The Tale of Genji (Murasaki 1981). To the outside world, mono no aware is most commonly associated with cherry-blossom viewing, where the short-lived existence of the falling cherry blossom is seen as a metonym for contemplation of the beauty in the transience of life itself. Although this mode of aestheticization shares disinterested and contemplative characteristics with the Kantian pure aesthetic gaze (Hughes 2010), its focus on pathos would seem to be at odds with commonly understood platonic Western ideals of beauty and art (c.f. Clark 1972; Saito 2007). However, the current paper aims to elucidate how perceptions of beauty of the pathetic have also been an aspect of Western thought and aestheticization practices, since early Christian times, more prominently in the Romantic era and even in Hollywood cinema. This is of particular significance to the current paper as Hollywood is often seen as a global metonym for glamour–the apparent antithesis of Japanese traditional aesthetics, such as mono no aware. To this end, an examination will be made of expressions of pathetic beauty in Tom Ford’s (2009) award-winning Hollywood film, A Single Man, and how this relates to parallels in the development of aesthetic thought in the occident and Japan.