In 1963--a racially-charged time in the United States--James Baldwin delivered "A Talk to Teachers," urging educators to engage youth in difficult conversations about current events. We concur with Giroux (2011, 2019) that political forces influence our educational spaces and that classrooms should not be viewed as apolitical, but instead seen as sites for engagement, where educators and artists alike can "go for broke." Drawing upon A Tribe Called Quest's 2017 Grammy performance of "We the People..." as an example of the role of the arts in troubled times, we consider ways to work alongside youth in schools to respond, consider, and process current events through music.