The purpose of this paper is to investigate Paul Muldoon’s playful elegiac recollection in two ways: his adoption of dark humor and his association techniques. As a dark humorist Muldoon reflects on desperate existential, historical, and political crises of the era; yet he does not simply remain as a serious melancholic, neither as a traditional elegist who emphatically narrows the distance between the environment in mourning and himself nor as a modern elegist who helplessly falls into a melancholic abyss. The anomalous mixture of the melancholic and the humorous is delivered through the poet’s nuanced word choices, shibboleth, and play of signifiers, all of the association techniques creating tension between objects and context, placed at the limit of signification. In lamenting the turbulent era, Muldoon maintains a humorous distance from the traumatic history, leaving traceable clues that instantly drift into the play of signifiers.