This article reflects the trend within the stylistics of drama towards the analysis of film and television discourse by examining dialogue from HBO’s popular organised crime drama The Sopranos. A major theme of the series focuses on the consistent attempts of the authorities to bring Soprano gang members to justice for their crimes. To gather evidence, investigators rely on electronic surveillance and surreptitious listening devices worn by collaborating witnesses who agree to testify for the government against their former associates. FBI agents are additional participants in recorded conversations and they perform a range of discourse roles in these encounters. Cooperating witnesses employ a range of conversational strategies to accommodate FBI ‘eavesdroppers’, whilst the major criminal characters adopt tactics of conversational vigilance in their ‘crime talk’. Gangsters exercise a level of caution in their interactions which has important implications for conversational cooperation. This article will use Goffman’s (1981) participation framework to analyse how recorded crime talk is affected by the presence of investigating authorities and cooperating witnesses. The divergent conversational intentions of targets and cooperators also affect adherence to Grice’s (1975) conversational maxims. These seminal models will be applied to selective dialogue extracts from The Sopranos in order to demonstrate that criminal topics of conversation can have a significant effect on the structure and strategies of interactions in a television drama. Characters employ conversational caution when addressing incriminating acts which they consider it unwise to discuss explicitly. In many cases the external television audience is accommodated by being shown these crimes whilst internal overhearers are frustrated by the tactical vigilance adopted in characters’ talk.