According to Zillmann (2000) viewers function as “untiring moral monitors”; relentlessly coming to moral judgments about the actions and motives of protagonists and antagonists. How does this “moral monitoring” apply to morally ambiguous crime TV drama that features unlawful protagonists? The current exploratory study is based on qualitative interviews (N = 3 × 20) that aimed to provide insight in the grounds of moral evaluations of three selected episodes of mobster drama series The Sopranos. Viewers of three distinctive moral subcultures (i.e., prisoners, law enforcement agents, and civilians) were interviewed. The results revealed that the majority of prisoners and law enforcement agents grounded their moral evaluations mostly in their professional opinions and experiences, and came to fairly strict, yet different moral evaluations. In contrast, most of the civilians had a more “lenient” association with narratives and characters. Civilians generally based their evaluations on the morally ambiguous story world, and therefore showcased more nuances in their moral judgments.