Reality television that allegedly takes us inside organizations provides researchers with abundant data to consider how culture industries narrate and shape understandings of (un)idealized work practices. Within this context, we explored organizational dissent on the reality television show Undercover Boss. Recent research has theorized how dissent is a co-constructed process between dissenters and recipients. A challenge to exploring this process, however, is witnessing dissent as it unfolds over time and between supervisors and subordinates. Through a qualitative content analysis of eight seasons of Undercover Boss, we examined how the dissent life cycle was depicted. We determined beneath displays of exemplary employees and redeemed bosses vowing their commitment to employee concerns, a more problematic narrative existed. Despite attempts to highlight how employees can provide insightful, quality feedback, the program privileged showing bosses’ authority, business acumen, and how they facilitated and framed dissent messages. Dissent interactions ultimately supported executive business interests and demonstrated dysfunctional dissent processes.