This article will examine how the work environment presented through popular culture can enrich and extend ideas of work in a community college curriculum. The article presents the context and pedagogy of utilizing notions of “dirty jobs” in the classroom and highlights the discoveries made about theories of work in the process. Students documented these discoveries using three writing assignments. These scaffolded assignments created individual ethnographic responses to the key question: “What is Work”? By using meta-cognitive teaching practices and popular culture, students were able to use the guided writing activities to explore their individual notions of work, career, and passion. The article captures both the journey of the instructor and students as they make these discoveries through intentional writing activities premised on bell hook’s “pedagogies of engagement.