Every literary work emerges from the particular alternatives of its time. This is ostensibly reflected in the attempted innovative renderings of these alternatives in the poetry of contemporary Nigerian poets of Yoruba extraction. Discernible in the poetry of Niyi Osundare and Remi Raji is the shaping and ordering of the linguistic appurtenances of the Yoruba orature, which themselves are sublimely rooted in the proverbial, chants, anecdotes, songs and praises derived from the Yoruba oral poetry of Ijala, Orin Agbe, Ese Ifa, Rara, folklore as well as from other elements of oral performance. This engagement with the Yoruba oral tradition significantly permeates the poetics of Niyi Osundare’s Waiting laughters and Remi Raji’s A Harvest of Laughters. In these anthologies, both Osundare and Raji traverse the cliffs and valleys of the contemporary Nigerian milieu to distil the social changes rendered in the Yoruba proverbial, as well as its chants and verbal formulae, all of which mutate from momentary happiness into an enduring anomie grounded in seasonal variations in agricultural production, ruinous political turmoil, suspense and a harvest of unresolved, mysterious deaths. The article is primarily concerned with how the African oral tradition has been harnessed by Osundare and Raji to construct an avalanche of damning, peculiarly Nigerian, socio-political upheavals (which are essentially delineated by the signification of laughter/s) and display these in relation to the country’s variegated ecology.