This chapter provides a first-hand, in-depth insight into humor-based activist–organization interaction based on a single case study. Although extensively examined in social science literature, 1 humor is arguably not a characteristic that is frequently associated with activism in mainstream Western culture and psyche. Historically, business and communication scholars have examined the activist–business relationship primarily through an organizational lens. In providing an alternative—activist-focused—perspective, this chapter addresses an existing gap in the literature. It challenges current understanding and assumptions, and hence the way businesses seek out to engage with activists and ‘manage’ opposition. Based on in-depth observations I argue that comedy, wit and hilarity have traditionally performed a crucial role in activist communication and continue to do so today. However, the communication styles and tools utilized by activists tend to differ from those used by professional organizations, which employ humor for very specific and distinct purposes. The unfamiliarity and adverse connotations associated with street theater, clowning and playful communication in a business context may lead to activists being injudiciously misunderstood or dismissed as unprofessional and amateurish. However, much of this conclusion may be based on misconceptions and the assumption that humorous protests are targeted at and performed for the benefit of organizational representatives, which is being contested in this chapter.