This dissertation takes issue with recent injunctions against mourning in contemporary trauma studies. The critical turn to melancholic or "resistant mourning" is based on the idea that one normalizes and assimilates loss in ethically dubious ways, either denying the loss or denying the alterity of the lost other; as a result, this criticism positions melancholia as the only viable response against a totalizing mourning. In tracing the parallels between this trend and a related valorization of anti-elegiac tendencies in twentieth and twenty-first century writing, I argue that the resurgent discourse of melancholia is based on a perceived breakdown of mourning which paradoxically conceals a desire for a time of perfect, totalizing mourning that this trend ostensibly refutes. This thesis, which most centrally addresses recent trends in trauma studies, opens up to postcolonial studies by examining how contemporary Anglophone writers, shaped by a common traumatic history of English colonialism, attempt to articulate new modes of grief work rather than simply returning to old wounds. Focusing on representations of individual loss and historical trauma in the work of Kamau Brathwaite, J. M. Coetzee, Zakes Mda, and Derek Walcott, I explore acts of literature as ways of working-through that do not actually foreclose a dialogic relationship with the past. While all four writers initially seem to participate in a valorization of melancholia, they are actually attempting to work through loss in ways that challenge a reductive binary opposition between mourning as closure and melancholia as openness.