This paper explores the cooperation taking place after the revolution of 2011 between the advertising industry, the state, and underground artists in Cairo. I argue that during times of transitions and political crises and when digital circulations are transforming the media industry in Egypt, the political power of art ceases to be deadlocked between defiance/resistance and compliance/selling out. Rather, political action during transitions transpires as a process of making sense of a world that appears ambiguous, cynical, and dreadful. In Cairo and since the early 2000s, emerging underground music scenes capitalizing on online platforms conjured alternative markets and youth publics adjacent to the mainstream media industry. After the 2011 revolution in Egypt, the advertising industry in Cairo started hiring underground musicians - instead of mainstream celebrities - to perform in commercials for a broad range of clients including the Egyptian government. The rise of the underground music scene after 2011 stilted on revolutionized youth subcultures and digital media, and spotlighted artists who flaunted their anti-corporatization and voiced their political engagement. Based on eighteen months of ethnographic fieldwork on the alternative music scene in Cairo, I explore the making of commercials (including a government’s sponsored national campaign) featuring underground musicians. I explain the power structures underpinning an incongruent collaboration transpiring during the years after 2011 between underground artists and their alleged antipodes: the corporates and government. The transformation brought by digital media intertwining with a new generation of youth audience is reshaping the media industry and restructuring the relation between governance, capital, and artists. On the one hand, corporates and governments piggyback on underground artists’ adept mastering of the online space and its social media to reach out to politicized younger generations. On the other hand, artists who need to channel cash flow to their music scenes through advertising deals have to negotiate between expectations of youth fan base looking up to the artists as the voice of the revolution and maneuvers with a government and corporates that they distrust and despise. The making of advertisements imbricates this mistrust and symbiosis between the state, capital, and artists, where actors are experimenting during transitional times when the rulebook of political action and media programming is transmuting. For underground artists, during transitions and crises, politics become the space where they can make sense of the world and actively engage with that which they also fight against; political oppression and industrialization of art.