A close examination of Wilde’s work reveals that lamentation and grief fuse with eroticism in such works as “The Fisherman and His Soul” and The Sphinx. The most renowned instance of the theme of necrophilia in Wilde is, of course, the dramatic scene of Salome’s erotic interaction with Jokanaan’s head. In Wilde’s decadent masterwork “Charmides,” a wood nymph’s sexual frustration in her futile attempt to revive the dead body of a male youth resembles the kommòs of Greek tragedy, the lyrical intensity of lament. The imbuement of mourning practices with Eros can be traced to the pastoral elegy The Epitaph of Adonis by the Hellenistic poet Bion of Smyrna. This chapter investigates the coalescence of necrophilia and mourning as a (post)Classical trope that crystallizes in Wilde’s work and further develops in the twentieth century. With a focus on “Charmides,” the first part of the chapter considers how Wilde, responding to the Hellenistic pastoral elegy and Adonian cults, employs tactics of misunderstanding and misapprehension as he amalgamates erotic with threnodic activity. The second part shows that the trope of necrophilic lament is fully fledged in Fernando Pessoa’s English Modernist poem Antinous. Wilde’s life and work were a decisive influence on the Portuguese poet. Emperor Hadrian’s quasi-pornographic grieving of his dead boy-lover Antinous in Pessoa’s vivid verse inherits Wilde’s poetics of ambivalence in which subversion is legitimized in cultural ritualism. The chapter aims at capturing Wilde’s hybrid worlds that transpire between Classicism and Modernism, lust and inertia, life and death.