Recent years have seen an explosion in the production and consumption of hip hop music in Nigeria. From the MTV Africa Music Awards to the BET Awards, Nigerian hip hop heads have continued to push the boundaries of their music on the international front, linking it, in the process, to a sort of global Hip Wide Web. Yet, despite these breakthroughs, the general perception of the discursive landscape of this music is not altogether positive in Nigeria itself. In particular, the message(s) of the music’s lyrics has been severally described as a venture that has no meaning beyond its noisy character. This is especially the case when the music is being evaluated by older generations of Nigerian critics who do not share in, and are almost averse to, the hip hop culture that has newly ascended as the dominant youth culture. Problematizing these evaluations under five paradigms—crossing, multilingualism, and styling, repetition, inversion of order, meaninglessness, and pornography—this essay contends that what appears as meaninglessness in Nigerian hip hop music inscribes a masked matrix of meanings in the postmodern age. It argues that the elements of the lyrical gamut that are often perceived as meaningless are in fact meaningful and valuable resources that the artists, and by extension their audience members, harness to perform their generational ingroupness and multiplex postmodern identities.