This book is a collection of academic essays that examines the representation, esthetics and dichotomy of the notions of grief and melancholy in East–West exchanges and cultural dialogues. It explores the topic in the dimensions of individual behaviors under specific social norms and cultural products such as literature, film and any other forms of arts/genres, etc. In his 1917 work Mourning and Melancholia (Trauer und Melancholie), Sigmund Freud connected the grief of loss with melancholic emotions which may give rise to acts of mourning. He suggested that “[i]n mourning it is the world which has become poor and empty; in melancholia it is the ego itself” (Freud, 1917: 246). Inspired by Freud’s stance and with the goal of providing up-to-date intellectual resources for academics, researchers and students with ardent interests in the varying exemplifications of grief and melancholy in Sino-Western contexts, the book serves more than a discussion over the pragmatic and ritualistic connections of grief and melancholy in relation to the inner self and the external world. It aims at the pursuit of a contemporary theorization of grief and melancholy beyond its modern limits.