Proverbs are a cherished mode of expression in many West African societies. As valuable sources of wisdom and coded utterances, a study of their use in the messaging of hiplife songs will be of considerable interest to scholars. Hiplife is an amalgamation of musical forms, an intriguing blend of traditional elements with novel forms of musical expression. Highlife music, a source of creativity for hiplife artists, abounds in proverbs and folk narratives. The chapter focuses on the use of proverbial expressions as verbal art forms in Ghanaian hiplife. The essay examines how these traditional forms are transposed and even modernized in hiplife. It discusses the role of these memorable devices in the social discourses of several hiplife songs. Furthermore, the chapter explores important themes and stylistic aspects of the songs and current trends in hiplife and, by extension, in hip-hop from West Africa and the black diaspora. Through the use of song text analyses and interviews, the chapter will fill an important gap in the literature of scholarly discussions about hiplife and highlife. By making aspects of such indigenous music accessible and meaningful to more people, the essay will help bridge the gap between local and global audiences of the two genres.