Shukr? Mabkh?t’s Al-?ily?n? (The Italian), a Tunisian novel that won the International Prize for Arabic Fiction in 2015, depicts a melancholic and narcissistic protagonist who appears to be haunted by his failure to engage in left-wing activity in the aftermath of the coup that deposed Tunisian president Habib Bourguiba, as well as by the author’s melancholia and sorrow over similar failures in the post-revolutionary present. Within the novel, the protagonist’s melancholia is linked to his inability to sustain the left-wing activism that he engaged in as a student; he gradually watches his dreams for political activity fail, eventually finding himself complicit in producing government propaganda. This type of melancholia can be described as “left-wing melancholy,” a term utilized by Walter Benjamin to criticize leftists who could not move beyond the failure of their projects. This melancholia is also linked to the protagonist’s wounded narcissism (a state that Freud believed caused a loss of ego-libido, which is here an object of loss that cannot be mourned and that results in melancholia), for which he tries to compensate by asserting his intelligence, virility and attractiveness to women. However, the timing of the novel’s publication (not long after the 2011 revolution) suggests that the melancholia in the novel may also contain a second dimension; perhaps it is also the result of the author’s disenchantment with the revolution that did not fulfill his hopes of bringing about successful left-wing political activity. The novel’s setting, during another period of disenchantment and failed political projects, could then be expressive of a melancholia belonging not only to that time but also to the present. The goal of this paper, therefore, is to examine the relationship between melancholia and narcissism in the novel, as well as the relationship between the melancholia of the past, when the novel is set, and the melancholia of the post-revolutionary present, in which the novel was written.