This chapter signals that mothering is the negotiated practice of motherhood; and that mothering is personal, cultural, and therefore political. In her analysis of Jamaican popular music, Getfield offers a uniquely nuanced approach to contextualizing lyrical representations of Black mothers, mothering, and single/sole motherhood by predominantly male artistes, wherever Jamaicans are domiciled, within the island nation and in diasporic regions such as Canada, the United States, and England. Getfield touches on common themes, including the appreciation of mothers; poverty and adversity; religion and spirituality; and mothers’ roles within Jamaica’s gun culture. As she underscores, there is a dearth of data on Jamaican mothering and motherwork in academic literature. Her chapter helps to fill this gap through the study of lyrical representations of mothers and the amplification of the voices of Jamaican artistes who are among those typically ignored in scholarly circles and in academic discussions about mothering practices and motherhood.