Education scholars and practitioners have much to learn about engagement and motivation of Black males by directing their inquiries to more organic sites of hip-hop cultural production outside of schools. One such site is the hip-hop's informal labor economy where Black males engage in earning money through hip-hop cultural production. Labor practices include a myriad of activities such as beat making, promoting shows, teaching dance classes, managing studios and recording sessions, artist development, visual art, and other modes of hip-hop cultural production. Through exploring the decision-making process of Black males that opt to participate in informal labor in lieu of formal labor, we examine what it is that compels their engagement and motivation efforts in hip-hop production. We find that participating in hip-hop cultural production gives Black males: (1) the autonomy to control their own image and maintain their individuality and (2) a sense of worth and belonging to something positive. From these findings, we discuss the need for schools to model themselves after such fields where Black males demonstrate high levels of engagement, motivation, and mastery.