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Humour plays a significant role in narrative storytelling but the extent to which it emerges (and is useful) during life history interviews with justice-involved populations remains unknown. The psychological value of “dark” or “gallows” humour is well established to buffer the impact of work stress, especially for emergency personnel or first responders. Drawing on the author’s experience of interviewing more than 80 men who served custodial sentences for sexual violence, this paper presents a preliminary typology to account for the ways that humour emerged in conversation. Articulating the identity of the “butt of the joke” led to a compelling trichotomy of punching up, punching down, and punching self. Punching up described participants who laughed at the expense of people in a position of power (such as a parent or a police officer). Participants who punched down made jokes about their less-savvy co-offenders, or laughed at their victims’ expense. Participants who engaged in self-deprecating humour were observed to be punching self. These examples are discussed within the context of the three predominant theories of humour: Incongruity Superiority, and Relief (Martin & Ford, 2018). Implications for narrative criminology and for narrative therapy with justice-involved individuals are discussed.